(cis-2-ethylcyclopent-1-yl)acetic acid | 82167-97-3

• 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
• 英文名称: (cis-2-ethylcyclopent-1-yl)acetic acid
• 英文别名: cis-(2-ethylcyclopentyl)acetic acid；2-[(1R,2R)-2-ethylcyclopentyl]acetic acid
• CAS: 82167-97-3
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: HDWRLHUKTLMVNC-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  重氮甲烷 、 (cis-2-ethylcyclopent-1-yl)acetic acid 以 乙醚 为溶剂， 生成 methyl cis-(2-ethylcyclopentyl)acetate
  参考文献：
  名称：

  Relationship of the anionic behavior of unsaturated medium-ring alcohols to structure. Generation and antarafacial cyclization of coiled 8.pi.-electron carbanions

  摘要：

  DOI：

  10.1021/ja00380a016
• 作为产物：
  描述：

  ethyl 2-ethyl-1-cyclopentenecarboxylate 在 Rh on carbon 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 20.0~110.0 ℃ 、586.06 kPa 条件下， 反应 63.0h， 生成 (cis-2-ethylcyclopent-1-yl)acetic acid
  参考文献：
  名称：

  Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles

  摘要：

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.

  DOI：

  10.1021/jo00031a031

文献信息

• Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles
  作者：Manning P. Cooke

  DOI：10.1021/jo00031a031

  日期：1992.2

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.
• Relationship of the anionic behavior of unsaturated medium-ring alcohols to structure. Generation and antarafacial cyclization of coiled 8.pi.-electron carbanions
  作者：Leo A. Paquette、Gary D. Crouse、Ashok K. Sharma

  DOI：10.1021/ja00380a016

  日期：1982.8