cis-2α-methylbicyclo<4.3.0>nonan-1β-ol | 101493-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2α-methylbicyclo<4.3.0>nonan-1β-ol
• 英文别名: (1R*,2S*,6S*)-2-methylbicyclo<4.3.0.>nonan-1-ol；(3aS,4R,7aR)-4-methyl-1,2,3,4,5,6,7,7a-octahydroinden-3a-ol
• CAS: 101493-12-3
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: SDYFKZGXGDSOBJ-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 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：

  3-methyl-oct-7-en-2-one 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 cis-2α-methylbicyclo<4.3.0>nonan-1β-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

• Lanthanides in organic synthesis. 3. A general procedure for five- and six-membered ring annulation
  作者：Gary A. Molander、Jeffrey B. Etter

  DOI：10.1021/jo00360a025

  日期：1986.5
• MOLANDER G. A.; ETTER J. B., J. ORG. CHEM., 51,(1986) N 10, 1778-1786
  作者：MOLANDER G. A.、 ETTER J. B.

  DOI：——

  日期：——