2-(2,2-diethoxyethyl)-7-tosyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole | 101481-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2,2-diethoxyethyl)-7-tosyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole
• 英文别名: (1S,12R)-15-(2,2-diethoxyethyl)-9-(4-methylphenyl)sulfonyl-9,15-diazatetracyclo[10.3.1.02,10.03,8]hexadeca-2(10),3,5,7-tetraene
• CAS: 101481-27-0
• 化学式: C₂₇H₃₄N₂O₄S
• 分子量: 482.644
• InChiKey: LAIOIOSROUATDG-YKSBVNFPSA-N

物化性质

• 沸点：
  619.2±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,2-diethoxyethyl)-7-tosyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 20.0h， 以79%的产率得到7-tosyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole
  参考文献：
  名称：

  A new synthetic entry to pentacyclic Strychnos alkaloids. Total synthesis of (.+-.)-tubifolidine, (.+-.)-tubifoline, and (.+-.)-19,20-dihydroakuammicine

  摘要：

  A new strategy for the synthesis of pentacyclic Strychnos alkaloids has been developed. It consists in the closure of the five-membered E ring by cyclization upon the indole 3-position from a suitably N-substituted tetracyclic system embodying rings ABCD of the alkaloids. Attempts to effect the key cyclization either by Pummerer rearrangement of sulfinylacetamides 4 and 6, from chloroacetamide 12, or from bis(methylthio)acetamide 10b (exocyclic amide carbonyl group) resulted in failure. In the first case dithioacetals 9 and 10, respectively, were formed in good yields. Cyclization from alcohol 13 or from the indole-deactivated acetal 15 and dithiocetal 18 were also unsuccessful: noncyclized products coming from the initially formed oxonium or thionium intermediates 16 were obtained. Cyclization was satisfactorily accomplished in 49% yield by treatment of the N-unsubstituted indole dithioacetal 23 with DMTSF. The resulting pentacycle 25 was converted to 20-deethyltubifolidine (27). A similar treatment from dithioacetal 41a, prepared from the secondary amine 32a, afforded pentacycle 42a, from which the alkaloids tubifoline, tubifolidine, and 19,20-dihydroakuammicine were synthesized.

  DOI：

  10.1021/jo00313a017
• 作为产物：
  描述：

  2-溴-1,1-二乙氧基乙烷 在 四丁基硫酸氢铵 sodium hydroxide 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 生成 2-(2,2-diethoxyethyl)-7-tosyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole
  参考文献：
  名称：

  五环马兜铃吲哚生物碱的新合成物

  摘要：

  DMTSF处理二硫缩醛15产生的硫鎓离子的环化构成Strychnos吲哚生物碱五环系统的新合成入口。

  DOI：

  10.1016/s0040-4039(00)94994-3