methyl (E)-3-<1'-<<2-(trimethylsilyl)ethoxy>methyl>-1'H-indol-2'-yl>prop-2-enoate | 153432-87-2

• 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: methyl (E)-3-<1'-<<2-(trimethylsilyl)ethoxy>methyl>-1'H-indol-2'-yl>prop-2-enoate
• 英文别名: methyl (E)-3-[1-(2-trimethylsilylethoxymethyl)indol-2-yl]prop-2-enoate
• CAS: 153432-87-2
• 化学式: C₁₈H₂₅NO₃Si
• 分子量: 331.487
• InChiKey: GTIMRGINWIRJHF-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 methyl (E)-3-<1'-<<2-(trimethylsilyl)ethoxy>methyl>-1'H-indol-2'-yl>prop-2-enoate 以 甲苯 为溶剂， 反应 72.0h， 生成 (3aS,4R,10cR)-2-Methyl-1,3-dioxo-6-(2-trimethylsilanyl-ethoxymethyl)-1,2,3,3a,4,5,6,10c-octahydro-pyrrolo[3,4-c]carbazole-4-carboxylic acid methyl ester 、 (3aS,4S,10cR)-2-Methyl-1,3-dioxo-6-(2-trimethylsilanyl-ethoxymethyl)-1,2,3,3a,4,5,6,10c-octahydro-pyrrolo[3,4-c]carbazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  A versatile new synthesis of 4-aryl- and heteroaryl-[3,4-c]pyrrolocarbazoles by [4+2] cycloaddition followed by palladium catalysed cross coupling

  摘要：

  4-Bromo- and 4-trifluorosulfonyloxypyrrolo[3,4-c]carbazoles were prepared in five steps via a [4+2] cycloaddition and were used as key intermediates in palladium-catalysed cross coupling reactions allowing the rapid generation of structurally diverse protein kinase C inhibitors. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01142-9
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 N-(2-(trimethylsilyl)ethoxymethyl)indole-2-carboxaldehyde 以 二氯甲烷 为溶剂， 生成 methyl (E)-3-<1'-<<2-(trimethylsilyl)ethoxy>methyl>-1'H-indol-2'-yl>prop-2-enoate
  参考文献：
  名称：

  A versatile new synthesis of 4-aryl- and heteroaryl-[3,4-c]pyrrolocarbazoles by [4+2] cycloaddition followed by palladium catalysed cross coupling

  摘要：

  4-Bromo- and 4-trifluorosulfonyloxypyrrolo[3,4-c]carbazoles were prepared in five steps via a [4+2] cycloaddition and were used as key intermediates in palladium-catalysed cross coupling reactions allowing the rapid generation of structurally diverse protein kinase C inhibitors. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01142-9

文献信息

• 2-(Tributylstannyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indole: Synthesis and use as a 1H-indol-2-yl-anion equivalent
  作者：Giovanni Palmisano、Marco Santagostino

  DOI：10.1002/hlca.19930760622

  日期：1993.9.22

  Pd-Catalyzed reaction of 2-(tributylstannyl)-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-indole (5) with a variety of aryl, heteroaryl, vinyl, and allyl halides provides an efficient entry to the corresponding cross-coupled products (see Table).

  2-（三丁基锡烷基）-1-[[2-（三甲基甲硅烷基）乙氧基]甲基} -1 H-吲哚（5）与各种芳基，杂芳基，乙烯基和烯丙基卤化物的钯催化反应提供了有效的途径相应的交叉耦合产品（请参见表）。