cis-1,1,1-Trifluor-2-phenyl-hexen-(2) | 15256-70-9

• 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: cis-1,1,1-Trifluor-2-phenyl-hexen-(2)
• 英文别名: (Z)-1-(1,1,1-trifluorohex-2-en-2-yl)benzene；[(Z)-1,1,1-trifluorohex-2-en-2-yl]benzene
• CAS: 15256-70-9
• 化学式: C₁₂H₁₃F₃
• 分子量: 214.23
• InChiKey: YTBYJYLINBXFQH-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-1,1,1-Trifluor-2-phenyl-hexen-(2) 在 C₃₂H₁₂BF₂₄^(1-)*C₃₄H₃₆IrNPS⁽¹⁺⁾ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、10.0 MPa 条件下， 反应 72.0h， 生成 (-)-1-(1,1,1-trifluorohexan-2-yl)benzene
  参考文献：
  名称：

  高选择性铱催化的三氟甲基烯烃的不对称加氢：一条新的路线到三氟甲基的立体中心。

  摘要：

  Abstractmagnified imageFluorine‐containing compounds are useful in many applications ranging from pharmaceuticals to ferroelectric crystals. We have developed a new, highly enantioselective synthetic route to trifluoromethyl‐bearing stereocenters in up to 96% ee via asymmetric hydrogenation using N,P‐ligated iridium catalysts. We also hydrogenated an isomeric mixture of olefins; this reaction gave the hydrogenation product highly enantioselectively (87% ee), and only the E isomer was present after the reaction had reached 56% conversion.

  DOI：

  10.1002/adsc.200800645
• 作为产物：
  描述：

  三丁基膦 、 2,2,2-三氟苯乙酮 以 正己烷 为溶剂， 生成 cis-1,1,1-Trifluor-2-phenyl-hexen-(2) 、 trans-1,1,1-Trifluor-2-phenyl-hexen-(2)
  参考文献：
  名称：

  Four-membered cyclic oxyphosphoranes. Isolation of stereoisomers at phosphorus and conversion into olefins and phosphinate esters

  摘要：

  DOI：

  10.1021/ja01026a030

文献信息

• The Reaction of Trifluoromethyl Ketones and Trialkylphosphines
  作者：Donald J. Burton、Frank E. Herkes、Kenneth J. Klabunde

  DOI：10.1021/ja00973a060

  日期：1966.11
• Four-membered cyclic oxyphosphoranes. Isolation of stereoisomers at phosphorus and conversion into olefins and phosphinate esters
  作者：Fausto Ramirez、Curtis P. Smith、J. F. Pilot

  DOI：10.1021/ja01026a030

  日期：1968.11
• Highly Selective Iridium-Catalyzed Asymmetric Hydrogenation of Trifluoromethyl Olefins: A New Route to Trifluoromethyl- Bearing Stereocenters
  作者：Mattias Engman、Pradeep Cheruku、Päivi Tolstoy、Jonas Bergquist、Sebastian F. Völker、Pher G. Andersson

  DOI：10.1002/adsc.200800645

  日期：2009.2

  Abstractmagnified imageFluorine‐containing compounds are useful in many applications ranging from pharmaceuticals to ferroelectric crystals. We have developed a new, highly enantioselective synthetic route to trifluoromethyl‐bearing stereocenters in up to 96% ee via asymmetric hydrogenation using N,P‐ligated iridium catalysts. We also hydrogenated an isomeric mixture of olefins; this reaction gave the hydrogenation product highly enantioselectively (87% ee), and only the E isomer was present after the reaction had reached 56% conversion.