(+)-3'-bromonormetazocine | 165673-94-9

• 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: (+)-3'-bromonormetazocine
• 英文别名: (1S,9S,13S)-5-bromo-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol
• CAS: 165673-94-9
• 化学式: C₁₄H₁₈BrNO
• 分子量: 296.207
• InChiKey: NSJGUFVULPOYDC-XOZVTBISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：

  3-甲基-2-丁烯醛 、 (+)-3'-bromonormetazocine 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 (+)-3'-bromo-5,9α-dimethyl-2-(3,3-dimethylallyl)-2'-hydroxy-6,7-benzomorphan
  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 pyridinium perbromate 、 溶剂黄146 作用下， 反应 1.5h， 以86%的产率得到(+)-3'-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

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.