(E)-9-(3,3,3-trifluoroprop-1-en-1-yl)phenanthrene | 1465812-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (E)-9-(3,3,3-trifluoroprop-1-en-1-yl)phenanthrene
• 英文别名: 9-[(E)-3,3,3-trifluoroprop-1-enyl]phenanthrene
• CAS: 1465812-81-0
• 化学式: C₁₇H₁₁F₃
• 分子量: 272.27
• InChiKey: BVRRUQWCDFOYPY-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-乙炔基菲 、 trifluoromethylcopper(I) 在 联硼酸频那醇酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以83%的产率得到(E)-9-(3,3,3-trifluoroprop-1-en-1-yl)phenanthrene
  参考文献：
  名称：

  Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF₃]

  摘要：

  A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.

  DOI：

  10.1021/acs.joc.7b00755

文献信息

• Julia–Kocienski approach to trifluoromethyl-substituted alkenes
  作者：Deborah O. Ayeni、Samir K. Mandal、Barbara Zajc

  DOI：10.1016/j.tetlet.2013.08.069

  日期：2013.11

  A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach. (C) 2013 Elsevier Ltd. All rights reserved.