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Quality Control of [ 145576-28-9 ] Purity: 98% SDS Specification

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Product Details of [ 145576-28-9 ]

CAS No. :	145576-28-9
Formula :	C₁₀H₁₆O₂
M.W :	168.23
SMILES Code :	CCOC(=O)C1CCC(=C)CC1
MDL No. :	MFCD12498694
InChI Key :	DLVGFWIRQAUWDC-UHFFFAOYSA-N
Pubchem ID :	15151435

Safety of [ 145576-28-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 145576-28-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.7
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	48.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.36
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.3
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.08
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.47
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.9
Solubility	2.11 mg/ml ; 0.0126 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.11
Solubility	1.32 mg/ml ; 0.00783 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.18
Solubility	1.12 mg/ml ; 0.00665 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.96 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.09

Application In Synthesis of [ 145576-28-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 145576-28-9 ]

[ 145576-28-9 ] Synthesis Path-Downstream 1~32

1
[ 17159-79-4 ]
[ 2065-66-9 ]
[ 145576-28-9 ]

Yield	Reaction Conditions	Operation in experiment
67%		Potassium tert-butoxide (24 gm, 0.22 moles) and triphenylphosphine methyl iodide (78 gm, 28.22 moles) were dissolved in dry tetrahydrofuran (150 ml). The mixture was cooled to -780C and stirred at the same temperature for about 15 minutes. Ethyl 4- oxocyclohexane carboxylate (25 gm, 0.147 moles) in tetrahydrofuran was added drop wise and the mixture was stirred at the same temperature for about 30 minutes and then it was warmed to room temperature and stirred overnight, extraction was done with ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated. Purification was done by column chromatography using 5% ethyl acetate in hexane. Yield: 19 gm (67%); m/z: (M++l) 169.26NMR: (delta, CDCl3) : 4.64 (2H, s), 4.09- 4.15 (2H, q), 2.42- 2.47 (IH, m), 2.31- 2.39 (2H, m), 1.96- 2.09 (4H, m), 1.43- 1.62 (2H, m), 1.23- 1.26 (3H, t)

References: [1]Patent: WO2010/46791,2010,A1 .Location in patent: Page/Page column 40.
[2]Journal of Organic Chemistry,1993,vol. 58,p. 2110 - 2114.

2
[ 145576-28-9 ]
[ 1004-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In diethyl ether; for 1h;Inert atmosphere; Reflux;	To a solution of ethyl 4-methylenecyclohexanecarboxylate (2 g, 11.89 mmol) in ether (40 mL) was added LAH (0.5 g, 13.17 mmol) portionwise under N2. The reaction mixture was refluxed for 1 h and was quenched by addition of 1 mL of EtOAc carefully and refluxed for 10 min. The reaction mixture was cooled down and added 3 mL of 1 N NaOH and stirred for 5 min, filtered off the solid and washed with ether. The filtration was washed with water, brine, dried (MgS04), and removed the solvent to afford (4-methylenecyclohexyl)methanol.

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 2110 - 2114.
[2]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 568.

3
[ 145576-28-9 ]
[ 74-95-3 ]
[ 147151-52-8 ]

Yield	Reaction Conditions	Operation in experiment
89%		n-BuLi (2.6 M in hexane, 2.5 mL, 6.6 mmoL) was added dropwisely to a solution of diisopropylamine (0.93 mL, 6.6 mmol) in THF (20 mL) at -78 C and stirred for 30 min at the same temperature. Hexamethylphosphoramide (4 mL) was added to the reaction mixture and stirred for 20 min at the same temperature. A solution of compound A 122-1 (1.01 g, 6 mmol) in THF (5 mL) was added and stirred for 1 h at the same temperature. A solution of dibromomethane (2.1 mL, 30 mmol) was added to the reaction mixture and the mixture was allowed to warm to room temperature for 1.5 h. The reaction mixture was diluted hexane (80 mL) and AcOEt (20 mL). The collected organic layer was washed with water, saturated NH4C1 aq., brine, dried over MgS04 and concentrated under reduced pressure. The residue was purified by silicagel chromatography (10% EtOAc/hexane as eluent) to provide compound A122-2 (1.39 g, 89%) as a pale yellow oil.

References: [1]Patent: WO2015/129926,2015,A1 .Location in patent: Page/Page column 103.
[2]Journal of Organic Chemistry,1993,vol. 58,p. 2110 - 2114.

4
[ 17159-79-4 ]
[ 1779-49-3 ]
[ 145576-28-9 ]

Yield	Reaction Conditions	Operation in experiment
95.7%		Triphenylmethylphosphonium bromide (53.7g, 0.15mol) was dissolved in 500mL of THF, and potassium tert-butoxide (16.8g, 0.15mol) was added at -20C. Reacted for 0.5h after the temperature was raised to 0 C. Subsequently, ethyl 4-oxo-cyclohexylcarboxylate (Compound 8-1) (17g, 0.1mol) was dissolved in 100mL of THF and added dropwise to the flask under nitrogen, reacted at room temperature for 3 hours, then a small amount of water was added to dissolve the solid, and rotary evaporated to remove THF, extracted with anhydrous diethyl ether, dried, and concentrated, the concentrate was dissolved in n-hexane, and filtered by silica gel, then concentrated to give Compound 8-2 as a colorless liquid (16.1g, 95.7% yield).
95.7%	With potassium tert-butylate; In tetrahydrofuran; hexane; water;	1) Ethyl 4-methylenecyclohexylcarboxylate (Compound 8-2) Triphenylmethylphosphonium bromide (53.7 g, 0.15 mol) was dissolved in 500 mL of THF, and potassium tert-butoxide (16.8 g, 0.15 mol) was added at -20 C. Reacted for 0.5 h after the temperature was raised to 0 C. Subsequently, ethyl 4-oxo-cyclohexylcarboxylate (Compound 8-1) (17 g, 0.1 mol) was dissolved in 100 mL of THF and added dropwise to the flask under nitrogen, reacted at room temperature for 3 hours, then a small amount of water was added to dissolve the solid, and rotary evaporated to remove THF, extracted with anhydrous diethyl ether, dried, and concentrated, the concentrate was dissolved in n-hexane, and filtered by silica gel, then concentrated to give Compound 8-2 as a colorless liquid (16.1 g, 95.7% yield).
85%		Example 6 Ethyl 4-meth lenecyclohexanecarboxylate19[0141] To a suspension of methyltriphenylphosphonium bromide (1.57 g, 4.41 mmol) in THF (9 mL) at -10 C was added w-BuLi (2.5 M in hexanes, 1.65 mL, 4.11 mmol) dropwise and the solution was allowed to stir for lh. Ethyl 4-oxocyclohexanecarboxylate (0.47 mL, 2.94 mmol) was added and the reaction was allowed to warm to room temperature over 3 h. Acetone (3 mL) was added and the solvent was removed under reduced pressure. The residue was suspended in dichloromethane and ethyl ether (1 : 1), filtered and concentrated. The crude was purified by flash column chromatography to afford 19 as clear oil (419 mg, 85%). H NMR: 1.25 (t, 3H), 1.50-1.70 (m, 2H), 1.90-2.16 (m, 4H), 2.30-2.50 (m, 3H), 4.12 (q, 2H), 4.65 (s, 2H).

84%		30A. Ethyl 4-methylenecyclohexanecarboxylate To a solution of (methyl)triphenylphosphonium bromide (5.18 g, 14.51 mmol) in THF (50 mL) at 0 C. was added n-butyllithium (9.07 mL, 14.51 mmol). The reaction mixture was stirred at 0 C. for 30 min. Ethyl 4-oxocyclohexanecarboxylate (1.9 g, 11.16 mmol) in THF (8 mL) was then added at 0 C. and the reaction was warmed to rt and stirred for 2 h. The reaction was quenched with sat'd aq. NH4Cl and diluted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (1.58 g, 84% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) delta 4.65 (s, 2H), 4.17-4.11 (m, 2H), 2.44 (tt, J=11.1, 3.8 Hz, 1H), 2.35 (dt, J=13.7, 4.0 Hz, 2H), 2.11-1.96 (m, 4H), 1.64-1.54 (m, 2H), 1.28-1.23 (m, 3H).
81%		Preparation of 4-Methylenecyclohexanecarboxylic acid ethyl ester; A suspension of methyl phosphonium bromide (3.15 g, 8.82 mmol) in dry THF (20 mL) was cooled to 00C, a solution of KtBuO (1.185 g, 10.58 mmol) in dry THF (15 mL) was added. The reaction mixture was allowed to rt and maintained for 1 h. The resulting mixture was cooled to 5-100C, 4-Oxo-cyclohexanecarboxylic acid ethyl ester (1.0 g, 5.88 mmol) (Chem. Abstr. Reg. No. 17159-79-4) was added over a period of 5 min, then was warmed to rt, maintained for 2h, then was heated to 50C and maintained over night additionally. The resulted reaction mass was diluted with water (200 mL) and extracted with EtOAc (200 mL). The organic layer was washed with water (50 mL), brine solution (100 mL), dried over anhydrous sodium sulfate and concentrated to obtain the crude product. The crude was purified by column chromatography over silica gel column using 3-4% EtOAc in pet ether as eluting solvent to obtain the pure product (1) as liquid (800 mg, 81%). 1HNMR(CDCI3): delta 4.65(s, 2H), 4.12(q, 2H), 2.3-2.5(m, 3H), 1.9-2.16(m, 4H), 1.5-1.7(m, 2H) and 1.25(t, 3H). Mass: (M+1) 169 calculated for Ci0H16O2.
76%		To a suspension of MePh3PBr (37.1 g, 104 mmol) in THF (500 mL) at 0C was added slowly LDA (1.2 eq) over 1 h. The resulting orange solution was stirred for 30 min before ethyl 4-oxocyclohexanecarboxyIate (16.1 g, 94.4 mmol) was added dropwise. The resulting suspension was warmed to rt and stirred overnight (may not necessary). A saturated NH4CI (aq) was added and THF was removed. The aqueous residue was extracted with EtOAc (100*3). The combined organic layers were washed with brine, dried over Na2S04 and concentrated. The residue was purified by passing through a short silica gel plug(hexanes/EtOAc 7:1). After being concentrated, ethyl 4-methylenecyclohexanecarboxylate was obtained as pale yellow oil (12.1 g, 76%).
73%		Lithium bis(trimethylsilyl)amide (1.0 M in THF, 15 mL, 15 mmol) was added dropwisely to a stirred solution of methyltriphenylphosphonium bromide (5.36 g, 15 mmol) in THF (50 mL) at 0 C and stirred for 40 min at the same temperature. A solution of ethyl 4-oxocyclohexanecarboxylate (2.04 g, 12 mmol) in THF (20 mL) was added slowly at 0 C and stirred for 2 h from 0 C to room temperature. The reaction was quenched with saturated NH4C1 aq. and extracted with hexane. The collected organic layer was dried over MgS04 and concentrated under reduced pressure. The solvent ( 100 mL, hexane/Et20 = 5/1) was added to the residue and stirred for 30 min. The suspension was filtrated. The filtrate was concentrated under reduced pressure. The residue was purified by silicagel chromatography (5% EtOAc/hexane as eluent) to provide compound A122-1 (1.478 g, 73%) as a colorless oil.
68.8%		N-butyllithium (21 mL, 52.5 mmol) was added dropwise to a solution of diisopropylamine (7.54 mL, 52.9 mmol) in THF (40 mL) at -78 C. over a period of 10 min. The resulted solution was stirred in an ice bath for 20 min. The above LDA solution was canulated into a suspension of methyltriphenylphosphonium bromide (19 g, 53.2 mmol) in THF (100 mL) in ice bath and the resulted mixture was stirred in the ice bath for 40 min. A solution of ethyl 4-oxocyclohexanecarboxylate (7.5 g, 44.1 mmol) in THF (20 mL) was added dropwise to this mixture. The reaction mixture was stirred for 18 h and diluted with hexane. The solid was filtered off and the filtrate was concentrated to afford a liquid. This crude product was plugged through silica gel pad (?2", EtOAc/hexane: 0 to 10%) to yield the title compound as a clear liquid (5.0 g, 68.8% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta 4.76-4.60 (m, 2H), 4.20-4.08 (m, 2H), 2.45 (tt, J=11.1, 3.6 Hz, 1H), 2.35 (dt, J=13.5, 3.5 Hz, 2H), 2.14-1.96 (m, 4H), 1.67-1.52 (m, 2H), 1.30-1.22 (m, 3H)
54%		Methyltriphenylphosphonium bromide (4.20 g, 11.75 mmol) and potassium 2-methylpropan-2-olate (1.32 g, 11.75 mmol) were dissolved in 1,4-dioxane (20 mL) under nitrogen. The solution was stirred for 30 min then cooled to 0 C. Separately, ethyl 4-methylenecyclohexane-1-carboxylate (1.06 g, 11.75 mmol) was dissolved in 1,4-dioxane (5 mL) and added dropwise over 15 min. The reaction mixture was stirred at 20 C for 1.5 h. The volatiles were removed under reduced pressure. The crude product was dissolved in DCM (30 mL) and filtered. The filtrate was purified via silica gel chromatography eluting with 0-40% EtOAc in heptane to afford ethyl 4-methylenecyclohexane-1-carboxylate 26 (1.06 g, 54%) as a clear oil. 1H NMR (400 MHz, CDCl3) 1.25 (t, J = 7.1, 3H), 1.50 - 1.66 (m, 2H), 1.93 - 2.13 (m, 4H), 2.34 (dt, J = 12.9, 3.7, 2H), 2.43 (tt, J = 10.9, 3.6, 1H), 4.13 (q, J = 7.1, 2H), 4.64 (t, J = 1.4, 2H). 1H NMR consistent with reported literature data4
		To a suspension of MePh3PBr (37.1 g, 104 mmol) in THF (500 mL) at 0C was added slowly LDA (1.2 eq) over 1 h. The resulting orange solution was stirred for 30 min before ethyl 4-oxocyclohexanecarboxylate (16.1 g, 94.4 mmol) was added dropwise. The resulting suspension was warmed to rt and stirred overnight. A saturated NH4CI (aq) was added and THF was removed. The aqueous residue was extracted with EtOAc (100mlx3). The combined organic layers were washed with brine, dried over Na2S04 and concentrated. The residue was purified by passing through a short silica gel plug (hexanes/EtOAc 7:1). After being concentrated, ethyl 4-methylenecyclohexanecarboxylate was obtained as a pale yellow oil (12.1 g).
		To a suspension of MePh3PBr (37.1 g, 104 mmol) in THF (500 mL) at 0 C was added slowly LDA (1.2 eq) over 1 h. The resulting orange solution was stirred for 30 min before ethyl 4-oxocyclohexanecarboxylate (16.1 g, 94.4 mmol) was added dropwise. The resulting suspension was warmed to rt and stirred overnight. A saturated NH4CI (aq) was added and THF was removed. The aqueous residue was extracted with EtOAc (100ml x 3). The combined organic layers were washed with brine, dried over Na2SC and concentrated. The residue was purified by passing through a short silica gel plug (hexanes/EtOAc 7:1). After being concentrated, ethyl 4-methylenecyclohexanecarboxyIate was obtained as a pale yellow oil (12.1 g).
3.5 g		Brief procedure: KO-tBu was added to a solution of methyltriphenylphosponium bromide at 0 C under nitrogen atmosphere and stirred for 30 min. To the above yellow colored reaction, a solution of ethyl 4-oxocyclohexane carboxylate in THF was added dropwise and the resulting mixture was stirred at the same temperature for 16 h. Work up: The reaction mixture was quenched with water and extracted with diethyl ether. The combined ethereal extract was dried and concentrated under reduced pressure. Purification: The crude residue was purified by silica gel (100-200 mesh) column chromatography by gradual elution from 5% to 10% EtOAc-petroleum ether. TLC system: 20% Ethyl acetate-petroleum ether, Rf value: 0.6 Nature of the compound: Colorless liquid, Yield: 3.5 g

References: [1]Patent: EP2738156,2014,A1 .Location in patent: Paragraph 0124-0125.
[2]Patent: US2014/179638,2014,A1 .Location in patent: Page/Page column.
[3]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.
[4]Patent: WO2012/142237,2012,A1 .Location in patent: Page/Page column 94.
[5]Patent: US2014/275173,2014,A1 .Location in patent: Paragraph 0421.
[6]Patent: WO2008/84300,2008,A1 .Location in patent: Page/Page column 47.
[7]Patent: WO2012/27234,2012,A1 .Location in patent: Page/Page column 64.
[8]Patent: WO2015/129926,2015,A1 .Location in patent: Page/Page column 102; 103.
[9]Patent: US2014/243298,2014,A1 .Location in patent: Paragraph 0351.
[10]Journal of the American Chemical Society,2018,vol. 140,p. 6873 - 6882.
[11]Journal of Medicinal Chemistry,2016,vol. 59,p. 8967 - 9004.
[12]Tetrahedron Letters,2018,vol. 59,p. 4479 - 4482.
[13]Patent: WO2012/27239,2012,A1 .Location in patent: Page/Page column 70.
[14]Patent: WO2012/27236,2012,A1 .Location in patent: Page/Page column 85.
[15]Patent: WO2015/4455,2015,A2 .Location in patent: Page/Page column 27.

5
[ 145576-28-9 ]
ethyl 3-hydroxy-4-methylenyl-1-cyclohexanecarboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

6
[ 145576-28-9 ]
cis-ethyl 3-hydroxy-4-methylenyl-1-cyclohexanecarboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

7
[ 145576-28-9 ]
cis-3-(Boc-amino)-4-methylenyl-1-cyclohexanoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

8
[ 145576-28-9 ]
trans-3-(Boc-amino)-4-methylenyl-1-cyclohexanoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

9
[ 145576-28-9 ]
cis-ethyl 3-(4'-nitrobenzoyloxy)-4-methylenyl-1-cyclohexanecarboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

10
[ 145576-28-9 ]
trans-3-amino-4-methylenyl-1-cyclohexanoic acid hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

11
[ 145576-28-9 ]
cis-3-amino-4-methylenyl-1-cyclohexanoic acid hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

12
[ 145576-28-9 ]
cis-ethyl 3-(N-Boc-N-ethyloxamate)-4-methylenyl-1-cyclohexanecarboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

13
[ 145576-28-9 ]
trans-ethyl 3-(N-Boc-N-ethyloxamate)-4-methylenyl-1-cyclohexanecarboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5719 - 5725.

14
[ 120-47-8 ]
aqueous NaOH [ No CAS ]
[ 145576-28-9 ]