(E)-1,3-diphenyl-2,4-dimethyl-1,3-pentadiene | 85267-86-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1,3-diphenyl-2,4-dimethyl-1,3-pentadiene
• 英文别名: (E)-2,4-dimethyl-1,3-diphenyl-1,3-pentadiene；[(1E)-2,4-dimethyl-1-phenylpenta-1,3-dien-3-yl]benzene
• CAS: 85267-86-3
• 化学式: C₁₉H₂₀
• 分子量: 248.368
• InChiKey: KEWNXXOUQYTOBV-JQIJEIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (1R,5S,6R)-4,4,6-trimethyl-1,5-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene 生成 (E)-1,3-diphenyl-2,4-dimethyl-1,3-pentadiene
  参考文献：
  名称：

  PADWA, A.;KUMAGAI, TSUTOMU;TOHIDI, MAHROKH, J. ORG. CHEM., 1983, 48, N 11, 1834-1840

  摘要：

  DOI：

文献信息

• Selective Double Carbomagnesiation of Internal Alkynes Catalyzed by Iron-N-Heterocyclic Carbene Complexes: A Convenient Method to Highly Substituted 1,3-Dienyl Magnesium Reagents
  作者：Yuesheng Liu、Lijun Wang、Liang Deng

  DOI：10.1021/jacs.5b12522

  日期：2016.1.13

  Controlled multicarbometalation of alkynes has been envisaged as an efficient synthetic method for dienyl and polyenyl metal reagents, but an effective catalyst enabling the transformation has remained elusive. Herein, we report that an iron(II)-N-heterocyclic carbene (NHC) complex (IEt2Me2)(2)FeCl2 (IEt2Me2 = 1,3-diethyl-4,5-dimethylimidazol-2-ylidene) can serve as a precatalyst for the double carbometalation of internal unsymmetrical alkynes with alkyl Grignard reagents, producing highly substituted 1,3-dienyl magnesium reagents with high regio- and stereoselectivity. Mechanistic studies suggest the involvement of low-coordinate organoiron(II)-NHC species as the in-cycle intermediates. The strong sigma-donating nature of IEt2Me2 and its appropriate steric property are thought the key factors endowing the iron-NHC catalyst fine performance.
• Studies dealing with the cycloreversion reactions of phenyl-substituted 2,3-diazabicyclo[3.1.0]hex-2-enes
  作者：Albert Padwa、Tsutomu Kumagai、Mahrokh Tohidi

  DOI：10.1021/jo00159a009

  日期：1983.6