(1R,2S,9S)-11-(2,2-dimethylpropyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (1R,2S,9S)-11-(2,2-dimethylpropyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane
• 英文别名: (1R,5S,11aS)-3-neopentyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine；(1R,2S,9S)-11-(2,2-dimethylpropyl)-7,11-diazatricyclo[7.3.1.02,7]tridecane
• 化学式: C₁₆H₃₀N₂
• 分子量: 250.428
• InChiKey: XKTIVYUOIHHBBU-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cytisine 在 platinum(IV) oxide sodium hydroxide 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 45.0h， 生成 (1R,2S,9S)-11-(2,2-dimethylpropyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane
  参考文献：
  名称：

  Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis

  摘要：

  Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.

  DOI：

  10.1021/jo049182w

文献信息

• PROCESSES AND INTERMEDIATES
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20130096277A1

  公开（公告）日：2013-04-18

  A process for preparing enantioselectively a compound of formula I-1a or I-1b: over a compound of formulas I-2-I-7:
• Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis
  作者：Michael J. Dearden、Matthew J. McGrath、Peter O'Brien

  DOI：10.1021/jo049182w

  日期：2004.8.1

  Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.