2-[1-(Benzenesulfonyl)-2-prop-2-enylindol-3-yl]ethyl 4-methylbenzenesulfonate | 1276539-10-6

• 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-[1-(Benzenesulfonyl)-2-prop-2-enylindol-3-yl]ethyl 4-methylbenzenesulfonate
• CAS: 1276539-10-6
• 化学式: C₂₆H₂₅NO₅S₂
• 分子量: 495.62
• InChiKey: JFDRABRMNCQUCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-(Benzenesulfonyl)-2-prop-2-enylindol-3-yl]ethyl 4-methylbenzenesulfonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 甲醇 、 potassium carbonate 、 magnesium 、 三乙胺 、 lithium iodide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 61.0h， 生成
  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：

  3-(2-hydroxyethyl)-1-(benzenesulfonyl)indole 在 4-二甲氨基吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-[1-(Benzenesulfonyl)-2-prop-2-enylindol-3-yl]ethyl 4-methylbenzenesulfonate
  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

• Exploration of Ring-Closing Enyne Metathesis for the Synthesis of ­Azonino[5,4-<i>b</i>]indoles
  作者：Daniel Solé、M.-Lluïsa Bennasar、Tomàs Roca、Magdalena Valldosera

  DOI：10.1002/ejoc.201501517

  日期：2016.3

  ring-closing enyne metathesis (RCEYM) as a methodology for the synthesis of the azonino[5,4-b]indole system, featuring the tricyclic substructure of the alkaloids cleavamine and quebrachamine, has been explored. Three series of enyne substrates were studied for their compatibility with the RCEYM reaction. In addition to the usual substrates bearing either a terminal or an internal alkyne, for the first

  已经探索了使用闭环烯炔复分解 (RCEYM) 作为合成 azonino[5,4-b] 吲哚系统的方法，该系统具有生物碱 cleavamine 和 quebrachamine 的三环亚结构。研究了三个系列的烯炔底物与 RCEYM 反应的相容性。除了带有末端或内部炔烃的常用底物外，还首次考虑了带有炔基卤化物部分的烯炔。尽管复分解环化允许在所有三个系列中组装 azoninoindole 核，但仅注意到内部炔烃底物的有效催化循环。根据实验结果，“yne-then-ene”途径似乎是这些反应中起作用的机制。
• 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.