| Identification | Back Directory | [Name]
(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE | [CAS]
1517-82-4 | [Synonyms]
menthyl p-toluenesulfinate
(S)-(-)-MENTHYL P-TOLUENESULFINATE
Menthyl (S)-4-methylbenzenesulfinate
(?-(1R)-Menthyl (S)-p-toluenesulfinate
(-)-(1R)-MENTHYL (S)-TOLUENE-4-SULFINATE
(-)-Menthyl (S)-4-methylbenzenesulfinate
(1R,2S,5R)-MENTHYL (S)-P-TOLUENESULFINATE
(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFITE
(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE
(S)-(-)-P-TOLUENESULFINIC ACID L-MENTHYL ESTER
p-Toluenesulfinic acid (1R,3R,4S)-menthyl ester
(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate,98%
p-Toluenesulfinic acid (1R,3R,4S)-p-menthane-3-yl ester
(1S)-2-Isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate
4-Methylbenzenesulfinic acid (1R,3R,4S)-p-menthane-3-yl ester
p-Toluenesulfinic acid (1R,1β)-2α-isopropyl-5β-methylcyclohexyl ester
p-Toluenesulfinic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester
(S)-((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyl) 4-Methylbenzenesulfinate
(S)-(-)-Menthyl p-toluenesulfinate, (-)-(1R)-Menthyl (S)-p-toluenesulfinate
4-Methylbenzenesulfinic acid (1R)-2α-isopropyl-5β-methylcyclohexane-1β-yl ester
[S(S)]-4-Methylbenzenesulfinic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester | [Molecular Formula]
C17H26O2S | [MDL Number]
MFCD00010192 | [MOL File]
1517-82-4.mol | [Molecular Weight]
294.45 |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [Melting point ]
99-104 °C
| [Boiling point ]
402.3±38.0 °C(Predicted) | [density ]
1.08 | [refractive index ]
-199 ° (C=1.5, Acetone) | [storage temp. ]
−20°C
| [solubility ]
Acetone (Slightly), Chloroform (Slightly) | [form ]
Solution | [color ]
Yellow to brown or gray | [Optical Rotation]
[α]20/D 195°, c = 2 in acetone | [BRN ]
3207468 |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Uses]
(1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate is a reactant used in the synthesis of sulfoxide pincer complexes of Mg, Rh and Ir. | [Uses]
(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate can react with:
- metal ketimines to form enantiopure sulfinimines
- p-(methylthio)benzaldehyde to form (S)-(-)-N-(4-methylthiobenzylidene)-p-toluenesulfinimine
| [General Description]
(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate is mainly used for the introduction of p-toluenesulfinyl group in asymmetric synthesis. | [Synthesis]
The general procedure for the synthesis of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinyl ester from p-toluenesulfinic acid and L-menthol was as follows: to a 250 mL flame-dried and N2 purged round-bottomed flask were added sequentially p-toluenesulfinic acid (0.525 g, 3.36 mmol), 4-bromobenzyl alcohol (0.598 g, 3.20 mmol) and DMAP (0.078 g, 0.64 mmol), which were then dissolved in anhydrous CH2Cl2 (14 mL). To this solution was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.644 g, 3.36 mmol) in a single addition and the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was diluted with CH2Cl2 (30 mL) and washed sequentially with 1M HCl (30 mL) and brine (30 mL). The organic layer was separated, dried with MgSO4, filtered and the solvent was removed under reduced pressure. Finally, the crude product was purified by fast column chromatography. | [References]
[1] Synthesis (Germany), 2018, vol. 50, # 24, p. 4855 - 4866
[2] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1646 - 1652
[3] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1646 - 1652
[4] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 356, p. 371 - 387
[5] Tetrahedron, 1999, vol. 55, # 8, p. 2311 - 2316 |
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