(2S)-(+)-1-叠氮基-3,3,3-三氟-2-丙醇 | 160595-62-0

• 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
• 中文名称: (2S)-(+)-1-叠氮基-3,3,3-三氟-2-丙醇
• 中文别名: 2-丙醇,3-叠氮-1,1,1-三氟-,(S)-
• 英文名称: (2S)-(+)-1-Azido-3,3,3-trifluoro-2-propanol
• 英文别名: (S)-3-azido-1,1,1-trifluoropropan-2-ol；(S)-(+)-1-Azido-3,3,3-trifluoro-2-propanol；(2S)-3-azido-1,1,1-trifluoropropan-2-ol
• CAS: 160595-62-0
• 化学式: C₃H₄F₃N₃O
• 分子量: 155.079
• InChiKey: BCRPFCFZQSDCHZ-REOHCLBHSA-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

• 作为反应物：
  描述：

  (2S)-(+)-1-叠氮基-3,3,3-三氟-2-丙醇 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (2S)-3-氨基-1,1,1-三氟-2-丙醇
  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
• 作为产物：
  描述：

  (S)-(-)-3,3,3-三氟2,3-环氧丙烷 在 sodium azide 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (2S)-(+)-1-叠氮基-3,3,3-三氟-2-丙醇
  参考文献：
  名称：

  Highly Stereocontrolled Access to 1,1,1-Trifluoro-2,3-epoxypropane via Lipase-Mediated Kinetic Resolution of 1,1,1-Trifluoro-3-(phenylthio)propan-2-ol and Its Application

  摘要：

  通过脂肪酶介导的相应酯类的动力学解析，制备出了对映体纯度很高的 1,1,1-三氟-3-(苯硫基)丙-2-醇。解析出的醇通过形成锍盐成功地转化为 1,1,1-三氟-2,3-环氧丙烷和/或在随后的反应中用作潜伏的 1,1,1-三氟-2,3-环氧丙烷。

  DOI：

  10.1246/bcsj.69.2655

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.
• Highly Stereocontrolled Access to 1,1,1-Trifluoro-2,3-epoxypropane via Lipase-Mediated Kinetic Resolution of 1,1,1-Trifluoro-3-(phenylthio)propan-2-ol and Its Application
  作者：Makoto Shimizu、Kouki Sugiyama、Tamotsu Fujisawa

  DOI：10.1246/bcsj.69.2655

  日期：1996.9

  1,1,1-Trifluoro-3-(phenylthio)propan-2-ol was prepared in high enantiomeric purity by lipase-mediated kinetic resolution of the corresponding esters. The resolved alcohol was successfully converted into 1,1,1-trifluoro-2,3-epoxypropane and/or used in the subsequent reactions as latent 1,1,1-trifluoro-2,3-epoxypropane via sulfonium salt formation.

  通过脂肪酶介导的相应酯类的动力学解析，制备出了对映体纯度很高的 1,1,1-三氟-3-(苯硫基)丙-2-醇。解析出的醇通过形成锍盐成功地转化为 1,1,1-三氟-2,3-环氧丙烷和/或在随后的反应中用作潜伏的 1,1,1-三氟-2,3-环氧丙烷。
• Catalytic asymmetric synthesis of new halogenated chiral synthons
  作者：Koen P. M. Vanhessche、K. Barry Sharpless

  DOI：10.1002/chem.19970030406

  日期：1997.4

  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.