2-methylbicyclo<4.4.0.>decan-1-ol | 65727-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylbicyclo<4.4.0.>decan-1-ol
• 英文别名: 4-methyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-4a-ol
• CAS: 65727-66-4
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: ABIYAQGCKAXEFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(4'-pentenyl)cyclohexanone 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以85%的产率得到2-methylbicyclo<4.4.0.>decan-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

• Electroorganic chemistry. 31. Reductive cyclization of nonconjugated olefinic ketones to cyclic tertiary alcohols
  作者：Tatsuya Shono、Ikuzo Nishiguchi、Hiroshi Ohmizu、Michiharu Mitani

  DOI：10.1021/ja00470a031

  日期：1978.1
• US9594303B2
  申请人：——

  公开号：US9594303B2

  公开（公告）日：2017-03-14