(1R*,2S*)-1-(2-hydroxy-2-methylcyclopent-1-yl)-2-propanone | 140902-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,2S*)-1-(2-hydroxy-2-methylcyclopent-1-yl)-2-propanone
• 英文别名: 1-[(1R,2S)-2-hydroxy-2-methylcyclopentyl]propan-2-one
• CAS: 140902-71-2
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: RWIMFVBDSMFDHS-BDAKNGLRSA-N

物化性质

• 沸点：
  241.7±13.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  庚-6-烯-2-酮 、 乙酸酐 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 生成 (1R*,2S*)-1-(2-hydroxy-2-methylcyclopent-1-yl)-2-propanone 、 (1R*,2S*)-1-methyl-2-(2-oxopropyl)cyclopentan-1-ol
  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.