反式-2-乙烯基环戊基乙酸 | 41309-52-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 反式-2-乙烯基环戊基乙酸
• 英文名称: trans-2-vinylcyclopentylacetic acid
• 英文别名: 2-vinylcyclopentylacetic acid；2-[(1S,2S)-2-ethenylcyclopentyl]acetic acid
• CAS: 41309-52-8；79299-05-1；82189-59-1；124918-96-3
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: DHSDKSDGRKEGOK-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-2-乙烯基环戊基乙酸 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 2-[(1S,2R)-2-(hydroxymethyl)cyclopentyl]acetic acid
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8
• 作为产物：
  描述：

  (E)-1-acetoxy-2,7-octadiene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 溶剂黄146 为溶剂， 生成 反式-2-乙烯基环戊基乙酸
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8

文献信息

• Yamamoto, Keiji; Terakado, Masahiko; Murai, Kouya, Chemistry Letters, 1989, p. 955 - 958
  作者：Yamamoto, Keiji、Terakado, Masahiko、Murai, Kouya、Miyazawa, Masahiro、Tsuji, Jiro、et al.

  DOI：——

  日期：——
• Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues
  作者：Masahiko Terakado、Kouya Murai、Masahiro Miyazawa、Keiji Yamamoto

  DOI：10.1016/s0040-4020(01)85639-8

  日期：——

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.