6-demethoxy-7α-<(1R)-1-p-tolylsulphonyloxyethyl>tetrahydro-6,14-endo-ethenothebaine | 135530-07-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 6-demethoxy-7α-<(1R)-1-p-tolylsulphonyloxyethyl>tetrahydro-6,14-endo-ethenothebaine
• CAS: 135530-07-3
• 化学式: C₂₉H₃₃NO₅S
• 分子量: 507.651
• InChiKey: KHGCUMMGKGZZGI-NCVZCJHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-demethoxy-7α-<(1R)-1-p-tolylsulphonyloxyethyl>tetrahydro-6,14-endo-ethenothebaine 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2'S,6α,7α,14α)-6-demethoxy-2'-methyl-5',6',6,7-tetrahydro-2'H,8H-1',5';6',14-dicyclopyrido<3',4':7,6>thebaine
  参考文献：
  名称：

  Steric factors in the azidolysis–thermolysis of some 5-tosyloxymethylbi-cyclo[2.2.2]oct-2-enes to yield 4-azatetracyclo[4.4.0.0.0]decanes

  摘要：

  Azidolysis of C-19 diastereoisomer tosylesters of morphine derivatives possessing a bridged ring C has been studied and 4-azatetracyclo[4.4.0(2.4).0(3.8)]decanes 6b, 6d and 6f were formed via the substitution and subsequent intramolecular cyclization of the (R)-C-19 tosylesters 4b, 4d and 4f, and primarily the ethylidene derivatives 7a, 7b and 7c were obtained from (S)-C-19 tosylesters 4c, 4e and 4g. According to our experience the course of the reaction depends on the configuration of the C-19 centre of chirality and on the spatial requirement of the substituent on C-6.

  DOI：

  10.1039/p19910001139
• 作为产物：
  描述：

  6-demethoxy-7α-thevinone 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.5h， 生成 6-demethoxy-7α-<(1R)-1-p-tolylsulphonyloxyethyl>tetrahydro-6,14-endo-ethenothebaine
  参考文献：
  名称：

  Steric factors in the azidolysis–thermolysis of some 5-tosyloxymethylbi-cyclo[2.2.2]oct-2-enes to yield 4-azatetracyclo[4.4.0.0.0]decanes

  摘要：

  Azidolysis of C-19 diastereoisomer tosylesters of morphine derivatives possessing a bridged ring C has been studied and 4-azatetracyclo[4.4.0(2.4).0(3.8)]decanes 6b, 6d and 6f were formed via the substitution and subsequent intramolecular cyclization of the (R)-C-19 tosylesters 4b, 4d and 4f, and primarily the ethylidene derivatives 7a, 7b and 7c were obtained from (S)-C-19 tosylesters 4c, 4e and 4g. According to our experience the course of the reaction depends on the configuration of the C-19 centre of chirality and on the spatial requirement of the substituent on C-6.

  DOI：

  10.1039/p19910001139