(R)-1-bromo-3,3,3-trifluoroisopropyl alcohol

• 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: (R)-1-bromo-3,3,3-trifluoroisopropyl alcohol
• 英文别名: (R)-(-)-1-Bromo-3,3,3-trifluoro-2-propanol；(R)-3-Bromo-1,1,1-trifluoropropan-2-ol；(2R)-3-bromo-1,1,1-trifluoropropan-2-ol
• 化学式: C₃H₄BrF₃O
• 分子量: 192.963
• InChiKey: VBHIIZIQRDVGDH-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-bromo-3,3,3-trifluoroisopropyl alcohol 以96%的产率得到
  参考文献：
  名称：

  Ramachandran P. Veeraraghavan, Gong Baoqing, Brown Herbert C., J. Org. Chem., 60 (1995) N 1, S 41-46

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-1,1,1-三氟丙酮 在 (+)-β-chlorodiisopinocampheylborane 、 二乙醇胺 作用下， 生成 (S)-(+)-1-Bromo-3,3,3-trifluoro-2-propanol 、 (R)-1-bromo-3,3,3-trifluoroisopropyl alcohol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00106a012

文献信息

• Method for Industrial Production of Optically Active Fluoroalkyl Ethylene Oxide
  申请人：Central Glass Company, Limited

  公开号：US20180312483A1

  公开（公告）日：2018-11-01

  It is possible to produce an optically active fluoroalkyl chloromethyl alcohol with a high optical purity and a good yield by treating a fluoroalkyl chloromethyl ketone with a microorganism having an activity for asymmetrically reducing the ketone or an enzyme having the activity. Then, it is possible to obtain a fluoroalkyl ethylene oxide by treating the alcohol with a base. Industrial implementation of the production method of the present invention is easy.

  通过使用具有对不对称还原酮具有活性的微生物或具有该活性的酶处理氟烷基氯甲基酮，可以生产出具有高光学纯度和良好产率的光学活性氟烷基氯甲基醇。然后，通过使用碱处理醇，可以获得氟烷基乙烯氧。本发明的生产方法易于工业实施。