(14Z)-11-(benzenesulfonyl)-17-ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,14,16-hexaene | 1276539-14-0

• 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: (14Z)-11-(benzenesulfonyl)-17-ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,14,16-hexaene
• CAS: 1276539-14-0
• 化学式: C₂₅H₂₆N₂O₂S
• 分子量: 418.56
• InChiKey: FSUVKHWLXNBPJE-NDENLUEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (14Z)-11-(benzenesulfonyl)-17-ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,14,16-hexaene 在 甲醇 、 magnesium 作用下， 反应 5.5h， 以88%的产率得到(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 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 67.0h， 生成 (14Z)-11-(benzenesulfonyl)-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

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.