2-(tert-butoxycarbonyl)-7-(phenylsulfonyl)-1,2,3,6-tetrahydroazocino[4,3-b]indole | 752212-14-9

• 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-(tert-butoxycarbonyl)-7-(phenylsulfonyl)-1,2,3,6-tetrahydroazocino[4,3-b]indole
• CAS: 752212-14-9
• 化学式: C₂₄H₂₆N₂O₄S
• 分子量: 438.547
• InChiKey: LCQBVWGJTRPMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.61
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(tert-butoxycarbonyl)-7-(phenylsulfonyl)-1,2,3,6-tetrahydroazocino[4,3-b]indole 在 盐酸 、 四(三苯基膦)钯 、 1,8-双二甲氨基萘 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 42.0h， 生成 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
• 作为产物：
  描述：

  2-allyl-3-[(N-allyl-N-tert-butoxycarbonylamino)-methyl]-1-(phenylsulfonyl)indole 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到2-(tert-butoxycarbonyl)-7-(phenylsulfonyl)-1,2,3,6-tetrahydroazocino[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

文献信息

• Total Synthesis of the Bridged Indole Alkaloid Apparicine
  作者：M.-Lluïsa Bennasar、Ester Zulaica、Daniel Solé、Tomàs Roca、Davinia García-Díaz、Sandra Alonso

  DOI：10.1021/jo901986v

  日期：2009.11.6

  radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine. From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents

  吲哚为模板的闭环复分解或2-二吲哚基自由基的环化反应，是为组装吲哚生物碱装置的三环ABC亚结构而开发的两种替代方法的主要步骤。从该关键中间体，分子内乙烯基卤化物Heck反应完成了生物碱的紧张的1-氮杂双环[4.2.2]癸烷骨架的闭合，同时伴随有环外亚烷基取代基的引入。