(2Z,4E)-1-(4-chlorophenyl)-5-phenyl-2,4-pentadien-1-ol | 1497434-26-0

• 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: (2Z,4E)-1-(4-chlorophenyl)-5-phenyl-2,4-pentadien-1-ol
• 英文别名: (2Z,4E)-1-(4-chlorophenyl)-5-phenylpenta-2,4-dien-1-ol
• CAS: 1497434-26-0
• 化学式: C₁₇H₁₅ClO
• 分子量: 270.758
• InChiKey: NMUCKQNWAYFPQF-HXGSSHHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-((4-chlorobenzyl)oxy)-1-phenyl-2-butyn-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 双(1,2-双(二苯基膦)乙烷)钯 、 三乙胺 、 红铝 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.58h， 生成 (2Z,4E)-1-(4-chlorophenyl)-5-phenyl-2,4-pentadien-1-ol 、 (2E,4E)-1-(4-chlorophenyl)-5-phenyl-2,4-pentadien-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of (2Z,4E)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (E)-4-Alkoxy-2-butenyl Benzoates

  摘要：

  The sequential 1,4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates and [1,2]-Wittig rearrangement gave (2Z,4E)-2,4-pentadien-1-ols stereoselectively. Z-Selective formation of intermediary vinyl ethers, whose stereochemistry was well elucidated by the "syn-effect", was achieved by treatment of the 2-butenyl benzoates with KOH in the presence of Pd catalyst. The subsequent [1,2]-Wittg rearrangement by use of n-BuLi proceeded with retention of the stereochemistry of the intermediary vinyl ethers.

  DOI：

  10.1021/jo402272r

文献信息

• Stereoselective Synthesis of (2<i>Z</i>,4<i>E</i>)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (<i>E</i>)-4-Alkoxy-2-butenyl Benzoates
  作者：Takeo Nakano、Takahiro Soeta、Kohei Endo、Katsuhiko Inomata、Yutaka Ukaji

  DOI：10.1021/jo402272r

  日期：2013.12.20

  The sequential 1,4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates and [1,2]-Wittig rearrangement gave (2Z,4E)-2,4-pentadien-1-ols stereoselectively. Z-Selective formation of intermediary vinyl ethers, whose stereochemistry was well elucidated by the "syn-effect", was achieved by treatment of the 2-butenyl benzoates with KOH in the presence of Pd catalyst. The subsequent [1,2]-Wittg rearrangement by use of n-BuLi proceeded with retention of the stereochemistry of the intermediary vinyl ethers.