(-)-R,R-2,8-dibromo-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid | 1478192-74-3

• 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-dibromo-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid
• CAS: 1478192-74-3
• 化学式: C₁₅H₁₂Br₂N₂*C₁₈H₁₄O₈
• 分子量: 738.386
• InChiKey: CTZGCEJVZYGVGG-DTPOWOMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  133.68
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (-)-R,R-2,8-dibromo-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-dibromo-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：

  (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate 、 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocine 以 1,2-二氯乙烷 为溶剂， 反应 120.0h， 以89%的产率得到(-)-R,R-2,8-dibromo-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