2-<(phenylsulfinyl)acetyl>-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole | 101481-19-0

• 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-<(phenylsulfinyl)acetyl>-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole
• CAS: 101481-19-0；101481-28-1
• 化学式: C₂₂H₂₂N₂O₂S
• 分子量: 378.495
• InChiKey: RTLBDBHDJVGAML-MUIFZSOGSA-N

物化性质

• 沸点：
  672.7±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-<(phenylsulfinyl)acetyl>-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole 在 三乙胺 、 三氟乙酸酐 作用下， 生成 2--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
• 作为产物：
  描述：

  2,3,4,5,6,7-hexahydro-1H-1,5-methanoazocino[4,3-b]indole 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-<(phenylsulfinyl)acetyl>-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

文献信息

• A new synthetic entry to pentacyclic Strychnos alkaloids. Total synthesis of (.+-.)-tubifolidine, (.+-.)-tubifoline, and (.+-.)-19,20-dihydroakuammicine
  作者：Mercedes Amat、Ana Linares、Joan Bosch

  DOI：10.1021/jo00313a017

  日期：1990.12

  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.