(-)-R,R-2,8-dimethoxy-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid | 1202533-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (-)-R,R-2,8-dimethoxy-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid
• CAS: 1202533-76-3
• 化学式: C₁₇H₁₈N₂O₂*C₁₈H₁₄O₈
• 分子量: 640.646
• InChiKey: HHMPZHMQXJGPRJ-DTPOWOMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  47.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  152.14
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (-)-R,R-2,8-dimethoxy-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以97%的产率得到2,8-dimethoxy-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
  参考文献：
  名称：

  Application of Crystallization-Induced Asymmetric Transformation to a General, Scalable Method for the Resolution of 2,8-Disubstituted Tröger’s Base Derivatives

  摘要：

  A general method for the gram scale resolution of 2-substituted and 2,8-disubstituted Troger's base (TB) derivatives in 63-91% yield has been achieved through the application of crystallization-induced asymmetric transformation (CIAT). Enantiomeric ratios of the resolved TB derivatives range from 99.1:0.9 to >99.5:0.5. Among the Troger's base compounds resolved are four synthetically valuable bromo and iodo derivatives.

  DOI：

  10.1021/jo401873x
• 作为产物：
  描述：

  2,8-dimethoxy-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine 、 (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate 以 1,2-二氯乙烷 为溶剂， 反应 120.0h， 以88%的产率得到(-)-R,R-2,8-dimethoxy-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid
  参考文献：
  名称：

  Application of Crystallization-Induced Asymmetric Transformation to a General, Scalable Method for the Resolution of 2,8-Disubstituted Tröger’s Base Derivatives

  摘要：

  A general method for the gram scale resolution of 2-substituted and 2,8-disubstituted Troger's base (TB) derivatives in 63-91% yield has been achieved through the application of crystallization-induced asymmetric transformation (CIAT). Enantiomeric ratios of the resolved TB derivatives range from 99.1:0.9 to >99.5:0.5. Among the Troger's base compounds resolved are four synthetically valuable bromo and iodo derivatives.

  DOI：

  10.1021/jo401873x

文献信息

• Chiral recognition of carboxylic acids by Tröger’s base derivatives
  作者：Sakilam Satishkumar、Mariappan Periasamy

  DOI：10.1016/j.tetasy.2009.08.030

  日期：2009.10

  The readily accessible optically active methoxy Troger's base 3 and the corresponding alpha,alpha'-diphenyl carbinol derivative 5 are useful for the recognition and enantiomeric discrimination of representative chiral carboxylic acids. (C) 2009 Elsevier Ltd. All rights reserved.