[ CAS No. 100-79-8 ] {[proInfo.proName]}

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2D 3D

Structure of 100-79-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 100-79-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100-79-8 ]

SDS Specification

Alternatived Products of [ 100-79-8 ]

Product Details of [ 100-79-8 ]

CAS No. :	100-79-8	MDL No. :	MFCD00063238
Formula :	C₆H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	HOCH₂C₃H₃O₂(CH₃)₂	InChI Key :	-
M.W :	132.16	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 100-79-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	32.21
TPSA :	38.69 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.71
Log Po/w (XLOGP3) :	-0.2
Log Po/w (WLOGP) :	0.13
Log Po/w (MLOGP) :	-0.26
Log Po/w (SILICOS-IT) :	0.84
Consensus Log Po/w :	0.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.47
Solubility :	45.1 mg/ml ; 0.341 mol/l
Class :	Very soluble
Log S (Ali) :	-0.16
Solubility :	92.2 mg/ml ; 0.698 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.52
Solubility :	40.1 mg/ml ; 0.303 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.09

Safety of [ 100-79-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 100-79-8 ]

* 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.

Upstream synthesis route of [ 100-79-8 ]
Downstream synthetic route of [ 100-79-8 ]

[ 100-79-8 ] Synthesis Path-Upstream 1~1

1
[ 100-79-8 ]
[ 102045-96-5 ]
[ 114746-70-2 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 39, p. 5319 - 5322

[ 100-79-8 ] Synthesis Path-Downstream 1~9

1
[ 100-79-8 ]
[ 5736-06-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With ruthenium trichloride; trichloroisocyanuric acid; tetrabutylammomium bromide; potassium carbonate; In water; acetonitrile; at 20℃; for 3h;	To a mixture of compound 1(350mg, 1.1 mmol) and RuCl3 (318 mg, 1.1 mmol) in MeCN (10 mL) and water (5 mL) were added K2C03 (455 mg, 3.3 mmol), TCCA and TBAB. The resulting mixture was stirred at rt for 3 h. The reaction was quenched with an aqueous solution ofNHCl and extracted with ethyl acetate. Organic layers were combined, dried over Na2SO4, concentrated to give 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid (450 mg, 75%). LC-MS: m/z = 147.4 [M+H]
30%	With potassium permanganate; potassium hydroxide; In water; for 2h;Cooling with ice;	Under ice-cooling, an aqueous (30 mL) solution of potassium permanganate (1.8 g, 11.3 mmol) was added dropwise to an aqueous (50 mL) solution of 2,2-dimethyl-1,3-dioxolane-4-methanol (1.0 g, 7.6 mmol) and potassium hydroxide (1.0 g, 15 mmol), and the mixture was stirred for 2 hours. The mixture was filtered on celite, and the filtrate was concentrated under reduced pressure. A saturated aqueous potassium hydrogen sulfate solution was added to the resulting filtrate until a pH thereof became 4. The mixture was extracted with ethyl acetate (200 mL×2), and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the titled reference compound (0.33 g) as a colorless oily product (Yield: 30%). [tabl0013-en] [Table 13] Reference compound 7-1 1H-NMR (500MHz, CDCl3) delta 4.62 (1H, dd, J = 7.6, 4.8Hz), 4.31 (1H, dd, J = 8.9, 7.6Hz), 4.20 (1H, dd, J = 8.9, 4.8 Hz), 1.54 (3H, s), 1.42 (3H, s)

Reference： [1]ACS Catalysis,2018,vol. 8,p. 6738 - 6744
[2]Patent: JP2005/75784,2005,A .Location in patent: Page/Page column 16-17; 22
[3]Angewandte Chemie - International Edition,2009,vol. 48,p. 559 - 563
[4]Patent: WO2016/44770,2016,A1 .Location in patent: Page/Page column 711
[5]Patent: EP3342768,2018,A1 .Location in patent: Paragraph 0123
[6]Helvetica Chimica Acta,1935,vol. 18,p. 598,599
[7]Chemistry of Penicillin,
[8]Chemical Communications,1998,p. 2361 - 2362
[9]Patent: WO2004/22530,2004,A1 .Location in patent: Page 33, 36
[10]Organic Process Research and Development,2004,vol. 8,p. 931 - 938

2
[ 30165-96-9 ]
[ 100-79-8 ]
[ 66492-30-6 ]

Reference： [1]Canadian Journal of Chemistry,1978,vol. 56,p. 722 - 724

3
[ 137944-39-9 ]
[ 100-79-8 ]
(4R,5R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-1,3-dimethyl-4,5-bis-(3-trifluoromethyl-phenyl)-[1,3,2]diazaphospholidine [ No CAS ]
(4R,5R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-1,3-dimethyl-4,5-bis-(3-trifluoromethyl-phenyl)-[1,3,2]diazaphospholidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 3326 - 3334

4
[ 1570-05-4 ]
[ 100-79-8 ]
3,4-bis-benzyloxy-benzoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 1411 - 1415

5
[ 335349-57-0 ]
[ 100-79-8 ]
[ 335349-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In dimethyl sulfoxide;	Example E5 (RS)-5-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4-iodo-2-nitro-phenylamine Prepared from <strong>[335349-57-0]5-chloro-4-iodo-2-nitro-phenylamine</strong> (Example A1) (4.48 g, 15 mmol), D,L-alpha, beta-isopropylidene-glycerol (10 mL, 81 mmol) and KOH (1.01 g, 18 mmol) in DMSO (10 mL) at 23 C. according to the general procedure E. Obtained as a yellow solid (4.9 g). MS (ISN) 393 [(M-H)-]; mp 151 C.

Reference： [1]Patent: US6407094,2002,B1

6
[ 30165-96-9 ]
[ 100-79-8 ]
(3-morpholino-1,2,5-thiadiazol-4-yloxy)-2,2-dimethyl-1,3-dioxolanyl methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tert-butyl alcohol;	Step A: <strong>[30165-96-9]3-Morpholino-4-chloro-1,2,5-thiadiazole</strong> (1 g., 5 mmole), 2,2-dimethyl-1,3-dioxolan-4-yl methanol (0.7 g., 5 mmole) were heated under reflux for 2 hours in t-butanol containing potassium t-butoxide (0.7 g.). The reaction mixture was diluted with water (10 ml.) and extracted twice with ethyl acetate. After washing with water and drying over magnesium sulfate, evaporation provided 1.35 g. (90%) of (3-morpholino-1,2,5-thiadiazol-4-yloxy)-2,2-dimethyl-1,3-dioxolanyl methane in the form of a yellow oil.

Reference： [1]Patent: US4076939,1978,A

7
[ 33332-28-4 ]
[ 100-79-8 ]
[ 1219130-25-2 ]

Yield	Reaction Conditions	Operation in experiment
50%		To a solution of solketal (48.7 g, 0.369 mol) in 1,4-dioxane (1500 mL) was added NaH (14.8 g, 369 mmol) at room temp and stirred for 2 h. Then 6-chloropyrazin-2-amine (34; 16.0 g, 123 mmol) was added and the mixture was stirred at 120 °C for 12 h. The solvent was removed and ethyl acetate (1000 mL) was added. The mixture was washed with brine (1000 mL x 3), The organic solvent was dried over Na2SO4, concentrated in vacuo and purified by chromatography on silica gel (dichloromethane:methanol=30:l-10:l) to give 6-((2,2-dimethyl-l,3-dioxolan-4- yl)methoxy)pyrazin-2-amine (35; 13.8 g, 61.3 mmol, 50percent) as a yellow solid. MS (ESI) calcd for C10H15N3O3 (m/z) 225.24, found: 226 [M+ H].

Reference： [1]Patent: WO2011/59839,2011,A1 .Location in patent: Page/Page column 78

8
[ 34259-99-9 ]
[ 100-79-8 ]
[ 54666-48-7 ]

Yield	Reaction Conditions	Operation in experiment
		NaH (60percent dispersion in mineral oil, 12.19 g, 305.3 mmol) was added portionwise to DL- 1 ,2-isoproylideneglycerol (16.1 1 g, 1218 mmol) and the mixture was stirred until gas evolution had ceased (ca. 30 min RT, followed by 2 h at 60°C). Subsequently, 4- bromothiazole (20.00 g, 121 .9 mmol) was added and the mixture was stirred at 140°C for 45 min. Subsequently, the reaction mixture was quenched with aq. sat. NH4CI and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgS04, and cone, in vacuo. The residue was subjected to distillation and the volatiles (HV, 60°C)were removed. The residue was purified by means of CC (5-40percent EtOAc/Hept) to provide a yellow oil. LC-MS (3): tR = 0.52 min; [M+H]+: 216.20.
		A.1.10.1. 4-((2,2-Dimethyl-1 ,3-dioxolan-4-yl)methoxy)thiazole NaH (60percent dispersion in mineral oil, 12.19 g, 305.3 mmol) was added portionwise to DL- 1 ,2-isoproylideneglycerol (16.11 g, 1218 mmol) and the mixture was stirred until gas evolution had ceased (ca. 30 min RT, followed by 2 h at 60°C). Subsequently, 4- bromothiazole (20.00 g, 121.9 mmol) was added and the mixture was stirred at 140°C for 45 min. Subsequently, the reaction mixture was quenched with aq. sat. NH4CI and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgS04, and cone, in vacuo. The residue was subjected to distillation and the volatiles (HV, 60°C) were removed. The residue was purified by means of CC (5-40percent EtOAc/Hept) to provide a yellow oil. LC-MS (3): tR = 0.52 min; [M+H]+: 216.20.

Reference： [1]Patent: WO2014/115078,2014,A1 .Location in patent: Page/Page column 43-44
[2]Patent: WO2014/115072,2014,A1 .Location in patent: Page/Page column 51

9
[ 156897-06-2 ]
[ 100-79-8 ]
rac-[2-(4-chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 3h;	Step 1 : Synthesis of rac-[2-(4-chloro-phenyl)-6,6-dimethyl-l-phenyl-6,7-dihydro-5H- pyrrolizin-3-yl] -acetic acid 2,2-dimethyl-[l,3]dioxolan-4-ylmethyl ester (0169) 1.74 g (13.2 mmol) rac-(2,2-dimethyl-[l,3]dioxolan-4-yl)-methanol, 1.82 g (9.5 mmol) EDCxHCl and 0.05 g (0.4 mmol) DMAP were dissolved in 15 ml THF. 3 g (7.9 mmol) 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro- lH-pyrrolizin-5-yl] acetic acid (<strong>[156897-06-2]licofelone</strong>) dissolved in 20 ml THF were dropped into this solution within 15 min. The reaction mixture was kept under continuous stirring at RT for 3 hours. Stirring was stopped and the solvent was decanted off. The decanted organic layer was evaporated and the obtained yellow oily product was subjected to flash chromatography (ethyl acetate/n-heptane 1 :2 (v/v)) to yield the oily product. To the yellow oil 50 ml n- pentane were added while stirring. A slightly yellow to white solid precipitated. After stirring for 1 hour, the product was filtered off and dried for 2 hours at RT at 21 mbar. (0170) 1H NMR (400 MHz, acetone- d6) delta [ppm] : 1.30 (s, 5 H) 1.34 (s, 1 H) 2.80 - 2.83 (m, 1 H) 3.60 (s, 1 H) 3.74 (dd, J=8.41, 6.06 Hz, 0.5 H) 3.82 (s, 1 H) 4.07 (dd, J=8.21, 6.65 Hz, 0.5 H) 4.17 (dd, J=5.08, 3.52 Hz, 1 H) 4.32 (d, J=4.69 Hz, 0.5 H) 7.03 - 7.07 (m, 1 H) 7.15 - 7.19 (m, 2 H) 7.30 (d, J=8.21 Hz, 1 H)

Reference： [1]Patent: WO2017/68053,2017,A1 .Location in patent: Page/Page column 26

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Isomers

Technical Information

? Appel Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Hydride Reductions ? Jones Oxidation ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Nomenclature of Ethers ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Amines ? Preparation of Ethers ? Reactions of Alcohols ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Swern Oxidation

Historical Records

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[ 100-79-8 ]

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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 100-79-8 ] {[proInfo.proName]}

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[ 100-79-8 ] Synthesis Path-Upstream 1~1

[ 100-79-8 ] Synthesis Path-Downstream 1~9

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Alcohols

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