(2S)-(-)-1-Cyano-3,3,3-trifluoro-2-propanol | 160595-64-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2S)-(-)-1-Cyano-3,3,3-trifluoro-2-propanol
• 英文别名: (S)-(-)-1-Cyano-3,3,3-trifluoro-2-propanol；(S)-4,4,4-Trifluoro-3-hydroxy-butyronitrile；(3S)-4,4,4-trifluoro-3-hydroxybutanenitrile
• CAS: 160595-64-2
• 化学式: C₄H₄F₃NO
• 分子量: 139.077
• InChiKey: NCKPCYRKCHNXIW-VKHMYHEASA-N

物化性质

• 沸点：
  231.7±40.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 (2S)-(-)-1-Cyano-3,3,3-trifluoro-2-propanol 在 氢气 作用下， 生成 乙基(3S)-4,4,4-三氟-3-羟基丁酸酯
  参考文献：
  名称：

  Bussche-Huennefeld, Christoph von .; Cescato, Claudio; Seebach, Dieter, Chemische Berichte, 1992, vol. 125, # 12, p. 2795 - 2802

  摘要：

  DOI：
• 作为产物：
  描述：

  Sulfuric acid mono-((S)-2-cyano-1-trifluoromethyl-ethyl) ester 在 硫酸 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (2S)-(-)-1-Cyano-3,3,3-trifluoro-2-propanol
  参考文献：
  名称：

  Catalytic asymmetric synthesis of new halogenated chiral synthons

  摘要：

  AbstractTwo‐step and practical asymmetric syntheses of enantiomerically pure 4‐trifluoromethyl‐2,2‐dioxo‐1,3,2‐dioxathiolane and 4‐trichloromethyl‐2,2‐dioxo‐1,3,2‐dioxathiolane (>98% ee) have been achieved. Catalytic asymmetric dihydroxylation (AD) of 3,3,3‐trifluoropropene and 3,3,3‐trichloropropene, respectively, is followed by direct cyclic sulfate formation by reaction with sulfuryl chloride. Opening of the cyclic sulfates with various nucleophiles provides easy access to important chiral synthons.

  DOI：

  10.1002/chem.19970030406

文献信息

• Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of Trifluoromethyloxirane. A General Synthesis in High Optical Purities of .alpha.-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide
  作者：P. Veeraraghavan Ramachandran、Baoqing Gong、Herbert C. Brown

  DOI：10.1021/jo00106a012

  日期：1995.1

  An extremely efficient one-pot asymmetric synthesis of either enantiomer of (trifluoramethyl)oxirane (3,3,3-trifluoro-1,2-epoxypropane, 4) in 64% yield and 96% ee has been achieved via the asymmetric reduction of the commercially available 1-bromo-3,3,3-trifluoro-2-propanone with either (+)- or (-)-B-chlorodiisopinocampheylborane (Aldrich: DIP-Chloride), followed by ring closure of the intermediate chloroborinate, IpcBCl[OCH(CH2Br)CF3]. The ring cleavage reactions of 4 provide a general synthesis of chiral trifluoromethyl carbinols without loss of optical activity. Thus we have synthesized 1-amino-3,3,3-trifluoro-2-propanol, 1-azido-3,3,3-trifluoro-2-propanol, 1-(diethylamino)3,3,3-trifluoro-2-propanol, 1-cyano-3,3,3-trifluoro-2-propanol, 1,1,1-trifluoro-2-propanol, 1,1,1-trifluoro-2-octanol, 1-phenyl-3,3,3-trifluoro-2-propanol, 1-ethoxy-3,3,3-trifluoro-2-propanol, and 1,2-dihydroxy-3,3,3-trifluorapropane, in 61-88% yields and in 96% ee by the cleavage of 4 with the appropriate nucleophile.