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Chemical Structure| 91-60-1 Chemical Structure| 91-60-1
Chemical Structure| 91-60-1

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CAS No.: 91-60-1

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Product Citations

Product Citations

Semenya, Julius ; Yang, Yuanjie ; Lee, Hye Joon , et al.

Abstract: Carbon-heteroatom bonds are of great importance due to their prevalence in pharmaceuticals, agrochemicals, materials, and natural products. Despite the effective use of metal-catalyzed crosscoupling reactions between sp2-hybridized organohalides and soft heteroatomic nucleophiles for carbon-heteroatom bond formation, the use of sp3-hybridized organohalides remain limited and the coupling with thiols remains elusive. Here, we report the coupling of sp3-hybridized benzyl or tertiary halides with soft thiol nucleophiles catalyzed by iron and extend the utility to alcohol and amine nucleophiles. The reaction is broad in substrate scope for both coupling partners and applicable in the construction of congested tri- and tetrasubstituted carbon centers as well as β-quaternary heteroatomic products. The synthetic utility is further emphasized by gram-scale synthesis and rapid herbicide library synthesis. Overall, we provide an efficient method to prepare pharmaceutically and materially relevant carbon-heteroatom bonds by expanding iron-catalyzed cross-coupling reactions to the coupling of sp3-hybridized organohalides with soft nucleophiles.

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Product Details of [ 91-60-1 ]

CAS No. :91-60-1
Formula : C10H8S
M.W : 160.24
MDL No. :MFCD00004086
InChI Key :RFCQDOVPMUSZMN-UHFFFAOYSA-N
Pubchem ID :7058

Safety of [ 91-60-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H314
Precautionary Statements:P501-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P405
Class:8(6.1)
UN#:2923
Packing Group:Ⅲ

Calculated chemistry of [ 91-60-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 51.2
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

38.8 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.13
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.11
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.13
Log Po/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.

3.61
Log Po/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

3.3
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.06

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.47
Solubility 0.0549 mg/ml ; 0.000342 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.59
Solubility 0.0409 mg/ml ; 0.000255 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

-4.17
Solubility 0.0108 mg/ml ; 0.0000675 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

 Yes
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

 Yes
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

 Yes
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.

-5.07 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

 2.0
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)

 1.0

Application In Synthesis [ 91-60-1 ]

* 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 [ 91-60-1 ]

[ 91-60-1 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 532-02-5 ]
  • [ 91-60-1 ]
  • 2
  • [ 532-02-5 ]
  • [ 91-60-1 ]
  • [ 135-19-3 ]
  • 3
  • [ 98541-64-1 ]
  • [ 91-60-1 ]
  • [ 159142-08-2 ]
  • 4
  • [ 532-02-5 ]
  • KSH [ No CAS ]
  • [ 91-20-3 ]
  • [ 5586-15-2 ]
  • [ 91-60-1 ]
  • [ 135-19-3 ]
  • 5
  • [ 130723-13-6 ]
  • [ 135049-02-4 ]
  • [ 91-60-1 ]
  • 3-bromo-5-trifluoromethylphenyl 2-naphthyl sulphide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In 2,4-dichlorophenoxyacetic acid dimethylamine; mineral oil; The 4-hydroxy-4-[3-(naphth-2-ylthio)-5-trifluoromethylphenyl]tetrahydropyran used as a starting material was obtained as follows: Sodium hydride (60% w/w dispersion in mineral oil; 0.5 g) was added portionwise to a mixture of 2-naphthalenethiol (1.42 g) and DMA (30 ml) and the mixture was stirred at ambient temperature for 1 hour. A solution of <strong>[130723-13-6]1-bromo-3-fluoro-5-trifluoromethylbenzene</strong> (2.43 g) in DMA (10 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography using hexane as eluent. There was thus obtained 3-bromo-5-trifluoromethylphenyl 2-naphthyl sulphide (1.37 g, 40%), as an oil. A solution of the product so obtained in THF (10 ml) was cooled to -60 C. and n-butyl-lithium (1.6M in hexane; 2.3 ml) was added dropwise.
40% In 2,4-dichlorophenoxyacetic acid dimethylamine; mineral oil; The 4-hydroxy-4-[3-(naphth-2-ylthio)-5-trifluoromethylphenyl]tetrahydropyran used as a starting material was obtained as follows:- Sodium hydride (60% w/w dispersion in mineral oil; 0.5 g) was added portionwise to a mixture of 2-naphthalenethiol (1.42 g) and DMA (30 ml) and the mixture was stirred at ambient temperature for 1 hour. A solution of <strong>[130723-13-6]1-bromo-3-fluoro-5-trifluoromethylbenzene</strong> (2.43 g) in DMA (10 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography using hexane as eluent. There was thus obtained 3-bromo-5-trifluoromethylphenyl 2-naphthyl sulphide (1.37 g, 40%), as an oil. A solution of the product so obtained in THF (10 ml) was cooled to -60C and n-butyl-lithium (1.6 M in hexane; 2.3 ml) was added dropwise.
  • 6
  • [ 52079-23-9 ]
  • [ 91-60-1 ]
  • [ 883998-42-3 ]
YieldReaction ConditionsOperation in experiment
21% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 80℃; under 760.051 Torr; for 14.16h; Example 1 1; Synthesis of (5)-2-hydroxy-4-(naphthalen-2-ylsulfonyl)-7V-((i?)-6-(piperidin- 1 -ylmethyl)- l,2,3,4-tetrahydronaphthalen-l-yl)butanamide; Step A: Synthesis of (iotaS)-2-hydroxy-4-(naphthalen-2-ylthio)butanoic acid; A solution of (5)-(-)-alpha-hydroxy-gamma-butyrolactone (505 mg, 4.947 mmol) and naphthalene-2-thiol (872 mg, 5.4 mmol) in DMF (20 mL) was cooled to 0 C under nitrogen, and treated with sodium hydride, 60% dispersion in mineral oil (416 mg, 10 mmol). After 10 minutes, the reaction was heated to 80 C for 14 h, cooled to 23 C, diluted with EtOAc (100 EPO <DP n="96"/>mL) and washed with 10% hydrochloric acid solution (50 mL) and brine (50 mL). The organic layer was dried over MgSOphi concentrated in vacuo and purified using silica gel chromatography (eluant: 2 - 5 - 10% methanol/dichloromethane), affording the title compound (274 mg, 21%) as a yellow solid. MS: 261.1 (M-H).
  • 7
  • [ 60940-34-3 ]
  • [ 91-60-1 ]
  • [ 1022195-18-1 ]
  • 8
  • [ 5424-47-5 ]
  • [ 91-60-1 ]
  • [ 23117-91-1 ]
  • 10
  • [ 18791-99-6 ]
  • [ 91-60-1 ]
  • 4-(naphthalen-2-ylthio)thiophene-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 105℃; for 24h;Inert atmosphere; [00879] Xantphos (154 mg, 10%) was added to a mixture of <strong>[18791-99-6]4-bromothiophene-2-carbonitrile</strong> (0.5 g, 2.66 mmol), NaO'Bu (306 mg, 3.18 mmol), naphthalene-2-thiol (51 1 mg, 3.19 mmol), Pd2dba3 (244 mg, 10%) and toluene (13.3 mL). The mixture was thoroughly degassed with argon and stirred at 105 C for 24 h. After cooling to rt, the mixture was filtered through celite and washed with EtOAc (50 mL). The organic phase was washed with 1 :1 H20/brine (80 mL), dried over MgSC , filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography (EtOAc/cyclohexane 0?5%) to afford the intermediate 4-(naphthalen-2-ylthio)thiophene-2- carbonitrile. This was dissolved in DCM (17.7 mL) and m-CPBA (70-75%; 1 .90 g, -7.98 mmol) was added portionwise. The mixture was allowed to stir at rt for 2 h. EtOAc (40 mL) was added and the organic phase was washed with sat NaHC03 (3 chi 40 mL), dried over MgS04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography (EtOAc/cyclohexane 0?70%) to afford 4-(naphthalen-2-ylsulfonyl)thiophene-2-carbonitrile as a white solid (509 mg, 64%).
 

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