(1R*,2S*)-2-(2-methyl-2-hydroxycyclopent-1-yl)acetic acid | 140902-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,2S*)-2-(2-methyl-2-hydroxycyclopent-1-yl)acetic acid
• 英文别名: 2-[(1R,2S)-2-hydroxy-2-methylcyclopentyl]acetic acid
• CAS: 140902-75-6
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: GBOJZWRPNZBFQV-SVRRBLITSA-N

物化性质

• 沸点：
  304.8±15.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  庚-6-烯-2-酮 、 二氧化碳 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 生成 (1R*,2S*)-2-(2-methyl-2-hydroxycyclopent-1-yl)acetic acid
  参考文献：
  名称：

  Samarium(II) iodide-induced reductive cyclization of unactivated olefinic ketones. Sequential radical cyclization/intermolecular nucleophilic addition and substitution reactions

  摘要：

  Samarium(II) iodide in the presence of HMPA effectively promotes the intramolecular coupling of unactivated olefinic ketones by a reductive ketyl-olefin radical-cyclization process. The reaction is quite general for the formation of 5- and 6-membered carbocycles and even provides modest yields in less facile cyclization processes as evidenced by the generation of methylcyclooctanol via an 8-endo cyclization. Sequential radical cyclization-intermolecular nucleophilic addition/substitution processes set the SmI2 reaction apart from its radical-chain, photochemical, and electrochemical counterparts. In addition to delineating the synthetic potential of this reaction, the role played by HMPA in enhancing SmI2 reactivity has been further refined, and a model correlating the high diastereoselectivity and product distribution in SmI2-promoted reductive coupling processes with HMPA concentration has been established.

  DOI：

  10.1021/jo00037a033

文献信息

• Samarium(II) iodide-induced reductive cyclization of unactivated olefinic ketones. Sequential radical cyclization/intermolecular nucleophilic addition and substitution reactions
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00037a033

  日期：1992.5

  Samarium(II) iodide in the presence of HMPA effectively promotes the intramolecular coupling of unactivated olefinic ketones by a reductive ketyl-olefin radical-cyclization process. The reaction is quite general for the formation of 5- and 6-membered carbocycles and even provides modest yields in less facile cyclization processes as evidenced by the generation of methylcyclooctanol via an 8-endo cyclization. Sequential radical cyclization-intermolecular nucleophilic addition/substitution processes set the SmI2 reaction apart from its radical-chain, photochemical, and electrochemical counterparts. In addition to delineating the synthetic potential of this reaction, the role played by HMPA in enhancing SmI2 reactivity has been further refined, and a model correlating the high diastereoselectivity and product distribution in SmI2-promoted reductive coupling processes with HMPA concentration has been established.