(E)-1-Phenyl-4-vinyl-undec-1-en-3-ol | 137256-03-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1-Phenyl-4-vinyl-undec-1-en-3-ol
• 英文别名: (E)-4-ethenyl-1-phenylundec-1-en-3-ol
• CAS: 137256-03-2
• 化学式: C₁₉H₂₈O
• 分子量: 272.431
• InChiKey: SAZZCHSJBGHQRZ-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  20.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 (E)-2-decenyl chloride 在 barium 作用下， 生成 (E)-1-Phenyl-4-vinyl-undec-1-en-3-ol 、 (1E,5E)-1-phenyl-1,5-tridecadien-3-ol
  参考文献：
  名称：

  Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds

  摘要：

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).

  DOI：

  10.1021/ja00093a010

文献信息

• Allylbarium in organic synthesis: unprecedented .alpha.-selective and stereospecific allylation of carbonyl compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Hisashi Yamamoto

  DOI：10.1021/ja00023a058

  日期：1991.11