2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole | 1276539-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole
• 英文别名: tert-butyl N-[2-[1-(benzenesulfonyl)-2-prop-2-enylindol-3-yl]ethyl]-N-prop-2-enylcarbamate
• CAS: 1276539-11-7
• 化学式: C₂₇H₃₂N₂O₄S
• 分子量: 480.628
• InChiKey: PQTWKIZPUNFOCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 甲醇 、 tris-(dibenzylideneacetone)dipalladium(0) 、 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene 、 magnesium 、 三乙胺 、 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 14.5h， 生成 (14Z)-17-ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,14,16-hexaene
  参考文献：
  名称：

  A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis−Vinyl Halide Heck Cyclization Strategy

  摘要：

  An indole-templated ring-closing metathesis has been used to create the central nine-membered ring of the cleavamine-type alkaloids. A subsequent intramolecular vinyl halide Heck reaction upon the resulting azacyclononene ring completes the assembly of the strained 1-azabicyclo[6.3.1]dodecane framework of the alkaloids. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine.

  DOI：

  10.1021/ol200437k
• 作为产物：
  描述：

  3-(2-hydroxyethyl)-1-(benzenesulfonyl)indole 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 、 lithium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 58.0h， 生成 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis−Vinyl Halide Heck Cyclization Strategy

  摘要：

  An indole-templated ring-closing metathesis has been used to create the central nine-membered ring of the cleavamine-type alkaloids. A subsequent intramolecular vinyl halide Heck reaction upon the resulting azacyclononene ring completes the assembly of the strained 1-azabicyclo[6.3.1]dodecane framework of the alkaloids. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine.

  DOI：

  10.1021/ol200437k

文献信息

• A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis−Vinyl Halide Heck Cyclization Strategy
  作者：M.-Lluïsa Bennasar、Daniel Solé、Ester Zulaica、Sandra Alonso

  DOI：10.1021/ol200437k

  日期：2011.4.15

  An indole-templated ring-closing metathesis has been used to create the central nine-membered ring of the cleavamine-type alkaloids. A subsequent intramolecular vinyl halide Heck reaction upon the resulting azacyclononene ring completes the assembly of the strained 1-azabicyclo[6.3.1]dodecane framework of the alkaloids. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine.
• Synthesis of cleavamine-type indole alkaloids and their 5-nor derivatives by a ring-closing metathesis–vinyl halide Heck cyclization strategy
  作者：M.-Lluïsa Bennasar、Daniel Solé、Ester Zulaica、Sandra Alonso

  DOI：10.1016/j.tet.2013.01.064

  日期：2013.3

  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.