(Z)-2-chloro-1-phenyl-4-phenylbut-3-en-1-ol

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (Z)-2-chloro-1-phenyl-4-phenylbut-3-en-1-ol
• 英文别名: (Z,1S,2S)-2-chloro-1,4-diphenylbut-3-en-1-ol
• 化学式: C₁₆H₁₅ClO
• 分子量: 258.748
• InChiKey: ASAQYVAWYGHXJK-KNBCMTEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  肉桂基氯 、 苯甲醛 在 indium(III) chloride 、 lithium diisopropyl amide 作用下， 生成 (Z)-2-chloro-1-phenyl-4-phenylbut-3-en-1-ol
  参考文献：
  名称：

  Preparation of γ-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds

  摘要：

  Various gamma-heteroatom-substituted allylindium reagents were prepared, and their reactions with carbonyl compounds were examined. The reaction of 1,3-dibromopropene with metallic indium gave two types of organoindium species, gamma-bromoallylindium and allylic diindium reagents. While the former gave 2-phenyl-3-vinyloxirane upon the coupling with benzaldehyde, the latter gave 1-phenylbut-3-en-1-o1. 1-Iodo-3-bromopropene gave the homoallylic alcohol exclusively. gamma-Alkoxyallylindium reagents were prepared by treating the corresponding gamma-alkoxyallyllithium with indium trichloride and reacted with benzaldehyde to give vic-diol mono ethers in high yields with good syn selectivity. gamma-(Trimethylsilyl)allylindium and alpha,gamma-disubstituted allylindium reagents were also prepared via transmetalation with the corresponding allyllithium.

  DOI：

  10.1021/jo9816111

文献信息

• Preparation of γ-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds
  作者：Tsunehisa Hirashita、Toshiya Kamei、Tomoaki Horie、Hatsuo Yamamura、Masao Kawai、Shuki Araki

  DOI：10.1021/jo9816111

  日期：1999.1.1

  Various gamma-heteroatom-substituted allylindium reagents were prepared, and their reactions with carbonyl compounds were examined. The reaction of 1,3-dibromopropene with metallic indium gave two types of organoindium species, gamma-bromoallylindium and allylic diindium reagents. While the former gave 2-phenyl-3-vinyloxirane upon the coupling with benzaldehyde, the latter gave 1-phenylbut-3-en-1-o1. 1-Iodo-3-bromopropene gave the homoallylic alcohol exclusively. gamma-Alkoxyallylindium reagents were prepared by treating the corresponding gamma-alkoxyallyllithium with indium trichloride and reacted with benzaldehyde to give vic-diol mono ethers in high yields with good syn selectivity. gamma-(Trimethylsilyl)allylindium and alpha,gamma-disubstituted allylindium reagents were also prepared via transmetalation with the corresponding allyllithium.