2-(5'-Hexenyl)-2-butenoic acid | 132156-68-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(5'-Hexenyl)-2-butenoic acid
• 英文别名: (2E)-2-ethylideneoct-7-enoic acid
• CAS: 132156-68-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: CZYOOQXBNVVUQS-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(5'-Hexenyl)-2-butenoic acid 在 草酰氯 作用下， 以98%的产率得到2-(5'-Hexenyl)-2-butenoyl chloride
  参考文献：
  名称：

  The generation and rearrangement of 2-(diazoacetyl)cyclobutanones: the formation of 5-spirocyclopropyl-2(5H)-furanones

  摘要：

  We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.

  DOI：

  10.1021/jo00004a022
• 作为产物：
  描述：

  6-溴-1-己烯 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 5.75h， 生成 2-(5'-Hexenyl)-2-butenoic acid
  参考文献：
  名称：

  The generation and rearrangement of 2-(diazoacetyl)cyclobutanones: the formation of 5-spirocyclopropyl-2(5H)-furanones

  摘要：

  We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.

  DOI：

  10.1021/jo00004a022

文献信息

• MILLER, R. D.;THEIS, W.;HEILIG, G.;KIRCHMEYER, S., J. ORG. CHEM., 56,(1991) N, C. 1453-1463
  作者：MILLER, R. D.、THEIS, W.、HEILIG, G.、KIRCHMEYER, S.

  DOI：——

  日期：——
• The generation and rearrangement of 2-(diazoacetyl)cyclobutanones: the formation of 5-spirocyclopropyl-2(5H)-furanones
  作者：Robert D. Miller、W. Theis、G. Heilig、S. Kirchmeyer

  DOI：10.1021/jo00004a022

  日期：1991.2

  We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.