(+)-1',3'-dibromo-N-normetazocine | 165882-64-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,7-苯并吗啡烷
• 英文名称: (+)-1',3'-dibromo-N-normetazocine
• 英文别名: (1S,9S,13S)-3,5-dibromo-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol
• CAS: 165882-64-4
• 化学式: C₁₄H₁₇Br₂NO
• 分子量: 375.103
• InChiKey: NSFBWBWTAIDXMI-IMIVBSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-1',3'-dibromo-N-normetazocine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96.8 mg的产率得到(+)-1'-bromonormetazocine
  参考文献：
  名称：

  Synthesis and .sigma. Binding Properties of 1'- and 3'-Halo- and 1',3'-Dihalo-N-normetazocine Analogs

  摘要：

  The synthesis and sigma 1 and sigma 2 binding properties of several 1'- and 3'-halo- and 1',3'-dihalosubstituted analogues of (+)-N-benzyl- and (+)- and (-)-N-dimethylallyl-N-normetazocine are presented. Structure-activity relationship analyses of the binding data showed that halogen substitution at the 1'-position of these N-substituted N-normetazocine analogues had little effect an ol binding affinity, whereas 3'-halo substitution as well as 1',3'-dihalo substitution resulted in a reduction of affinity. sigma 2 affinity was increased by the presence of a 3'-bromo substituent in this series of (+)-N-substituted N-normetazocines.

  DOI：

  10.1021/jm00015a023
• 作为产物：
  描述：

  (2alpha,6alpha,11R*)-1,2,3,4,5,6-六氢-6,11-二甲基-2,6-甲桥-3-苯并氮杂环辛四烯-8-醇 在 溴 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 以174 mg的产率得到(+)-1',3'-dibromo-N-normetazocine
  参考文献：
  名称：

  Synthesis and .sigma. Binding Properties of 1'- and 3'-Halo- and 1',3'-Dihalo-N-normetazocine Analogs

  摘要：

  The synthesis and sigma 1 and sigma 2 binding properties of several 1'- and 3'-halo- and 1',3'-dihalosubstituted analogues of (+)-N-benzyl- and (+)- and (-)-N-dimethylallyl-N-normetazocine are presented. Structure-activity relationship analyses of the binding data showed that halogen substitution at the 1'-position of these N-substituted N-normetazocine analogues had little effect an ol binding affinity, whereas 3'-halo substitution as well as 1',3'-dihalo substitution resulted in a reduction of affinity. sigma 2 affinity was increased by the presence of a 3'-bromo substituent in this series of (+)-N-substituted N-normetazocines.

  DOI：

  10.1021/jm00015a023

文献信息

• Synthesis and .sigma. Binding Properties of 1'- and 3'-Halo- and 1',3'-Dihalo-N-normetazocine Analogs
  作者：Richmond Danso-Danquah、Xu Bai、X. Zhang、S. Wayne Mascarella、Wanda Williams、Bethel Sine、Wayne D. Bowen、F. Ivy Carroll

  DOI：10.1021/jm00015a023

  日期：1995.7

  The synthesis and sigma 1 and sigma 2 binding properties of several 1'- and 3'-halo- and 1',3'-dihalosubstituted analogues of (+)-N-benzyl- and (+)- and (-)-N-dimethylallyl-N-normetazocine are presented. Structure-activity relationship analyses of the binding data showed that halogen substitution at the 1'-position of these N-substituted N-normetazocine analogues had little effect an ol binding affinity, whereas 3'-halo substitution as well as 1',3'-dihalo substitution resulted in a reduction of affinity. sigma 2 affinity was increased by the presence of a 3'-bromo substituent in this series of (+)-N-substituted N-normetazocines.