9,9-ethylenedioxy-3-endo-7-exo-dimethylbicyclo[3.3.1]nonan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9,9-ethylenedioxy-3-endo-7-exo-dimethylbicyclo[3.3.1]nonan-2-one
• 英文别名: (1'R,3'R,5'S,7'R)-3',7'-dimethylspiro[1,3-dioxolane-2,9'-bicyclo[3.3.1]nonane]-2'-one
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: AIOMUWGZXXDKNF-CHWFTXMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	9,9-ethylenedioxy-3-exo-7-exo-dimethylbicycli[3.3.1]nonan-2-one	——	C13H20O3	224.3

反应信息

• 作为产物：
  描述：

  9,9-ethylenedioxy-3-exo-7-exo-dimethylbicycli[3.3.1]nonan-2-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 9,9-ethylenedioxy-3-endo-7-exo-dimethylbicyclo[3.3.1]nonan-2-one
  参考文献：
  名称：

  Chair–boat equilibrium as driving force in epimerization of 3,7-dimethylbicyclo[3.3.1]nonan-2,9-dione derivatives. Stereocontrolled synthesis of the 3- exo ,7 -exo - and 3- endo ,7- exo -dimethylbicyclo[3.3.1]nonan-9-ones

  摘要：

  Molecular mechanics calculations and experimental H-1 NMR data are in close agreement and show that the epimerization equilibrium at C-3 Of 3,7-dimethylbicyclo[3.3.1]nonan-2,9-diones is shifted toward the 3-endo-epimer in order to reach the lowest energy chair-boat conformation. Introduction of a 1.3-dioxolane moiety at C-9 results in reversal of the equilibrium, in protic solvents, leading mainly to the 3-exo-epimer in the most stable chair-chair conformation. These results have been applied to the stereocontrolled synthesis of the title compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00445-8

文献信息

• Chair–boat equilibrium as driving force in epimerization of 3,7-dimethylbicyclo[3.3.1]nonan-2,9-dione derivatives. Stereocontrolled synthesis of the 3- exo ,7 -exo - and 3- endo ,7- exo -dimethylbicyclo[3.3.1]nonan-9-ones
  作者：Augusto Gambacorta、Daniela Tofani、Andrea Tafi、Mohamed Elmi Farah

  DOI：10.1016/s0040-4020(01)00445-8

  日期：2001.6

  Molecular mechanics calculations and experimental H-1 NMR data are in close agreement and show that the epimerization equilibrium at C-3 Of 3,7-dimethylbicyclo[3.3.1]nonan-2,9-diones is shifted toward the 3-endo-epimer in order to reach the lowest energy chair-boat conformation. Introduction of a 1.3-dioxolane moiety at C-9 results in reversal of the equilibrium, in protic solvents, leading mainly to the 3-exo-epimer in the most stable chair-chair conformation. These results have been applied to the stereocontrolled synthesis of the title compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.