(R)-1-phenylethyl trifluoroacetate | 58287-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-phenylethyl trifluoroacetate
• 英文别名: [(1R)-1-phenylethyl] 2,2,2-trifluoroacetate
• CAS: 58287-20-0
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: WVOSOYOZZDZROR-SSDOTTSWSA-N

物化性质

• 沸点：
  203.2±35.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-1-phenylethyl trifluoroacetate 、 苯酚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以65%的产率得到(S)-1-苯乙基苯基醚
  参考文献：
  名称：

  Formation of chiral aryl ethers from enantiopure amine or alcohol substrates

  摘要：

  Three methods for the preparation of chiral aryl ethers are demonstrated. N,N-Disulfonylimide derivatives are used in the stereoselective formation of aryl ethers from chiral amines. Nucleophilic attack of aryloxide anions on the cyclic N,N-disulfonylimide derivative of (S)-1-phenylethylamine afforded the (R)-1-phenylethyl phenyl and 2-naphthyl ethers with 83-87 and 70-79% inversion of configuration, respectively. The results are compared with results from alternative methods for the preparation of homochiral aryl ethers from chiral alcohols with complete retention and inversion of configuration, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00130-6
• 作为产物：
  描述：

  (R)-(+)-1-苯基乙醇 、 三氟乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到(R)-1-phenylethyl trifluoroacetate
  参考文献：
  名称：

  Formation of chiral aryl ethers from enantiopure amine or alcohol substrates

  摘要：

  Three methods for the preparation of chiral aryl ethers are demonstrated. N,N-Disulfonylimide derivatives are used in the stereoselective formation of aryl ethers from chiral amines. Nucleophilic attack of aryloxide anions on the cyclic N,N-disulfonylimide derivative of (S)-1-phenylethylamine afforded the (R)-1-phenylethyl phenyl and 2-naphthyl ethers with 83-87 and 70-79% inversion of configuration, respectively. The results are compared with results from alternative methods for the preparation of homochiral aryl ethers from chiral alcohols with complete retention and inversion of configuration, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00130-6

文献信息

• KONIG, WILFRIED A.;LUTZ, SABINE;WENZ, GERHARD, ANGEW. CHEM., 100,(1988) N, C. 989-990
  作者：KONIG, WILFRIED A.、LUTZ, SABINE、WENZ, GERHARD

  DOI：——

  日期：——
• Formation of chiral aryl ethers from enantiopure amine or alcohol substrates
  作者：Sadri A. Said、Anne Fiksdahl

  DOI：10.1016/s0957-4166(01)00130-6

  日期：2001.4

  Three methods for the preparation of chiral aryl ethers are demonstrated. N,N-Disulfonylimide derivatives are used in the stereoselective formation of aryl ethers from chiral amines. Nucleophilic attack of aryloxide anions on the cyclic N,N-disulfonylimide derivative of (S)-1-phenylethylamine afforded the (R)-1-phenylethyl phenyl and 2-naphthyl ethers with 83-87 and 70-79% inversion of configuration, respectively. The results are compared with results from alternative methods for the preparation of homochiral aryl ethers from chiral alcohols with complete retention and inversion of configuration, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.