(R)-(-)-1-Azido-3,3,3-trifluoro-2-propanol

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (R)-(-)-1-Azido-3,3,3-trifluoro-2-propanol
• 英文别名: (2R)-3-azido-1,1,1-trifluoropropan-2-ol
• 化学式: C₃H₄F₃N₃O
• 分子量: 155.079
• InChiKey: BCRPFCFZQSDCHZ-UWTATZPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,1,1-三氟-2,3-环氧丙烷 在 sodium azide 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (R)-(-)-1-Azido-3,3,3-trifluoro-2-propanol 、 (2S)-(+)-1-叠氮基-3,3,3-三氟-2-丙醇
  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

• 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.