4-ethyl-6-hydroxy-9-(phenylsulfonyl)-1,2,3,6,7,8-hexahydro-2,6-methanoazecino[4,3-b]indole | 1426162-88-0

• 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: 4-ethyl-6-hydroxy-9-(phenylsulfonyl)-1,2,3,6,7,8-hexahydro-2,6-methanoazecino[4,3-b]indole
• CAS: 1426162-88-0
• 化学式: C₂₄H₂₆N₂O₃S
• 分子量: 422.548
• InChiKey: GUJPLUKZZUMTDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.54
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(2-ethyl-3-iodo-2-propenyl)-7-(phenylsulfonyl)-1,2,3,6-tetrahydroazocino[4,3-b]indole 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,8-双二甲氨基萘 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以25%的产率得到4-ethyl-9-(phenylsulfonyl)-1,2,3,6-tetrahydro-2,6-methanoazecino[4,3-b]indole
  参考文献：
  名称：

  Synthesis of cleavamine-type indole alkaloids and their 5-nor derivatives by a ring-closing metathesis–vinyl halide Heck cyclization strategy

  摘要：

  An indole-templated RCM has been used to assemble the central medium-sized rings of the indole upper-half of vinorelbine and the cleavamine-type alkaloids. From these key intermediates, the bridged tetracyclic framework of the alkaloids is completed with the insertion of a 2-ethylpropeno unit, by N-alkylation followed by a challenging endocyclic vinyl halide Heck cyclization. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.064