Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate | 146681-76-7

• 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 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate
• 英文别名: N_b,N_b-dibenzyl-2-<(methoxycarbonyl)methyl>tryptamine；[3-(2-dibenzylaminoethyl)indol-2-yl]-acetic acid methyl ester；methyl 2-[3-[2-(dibenzylamino)ethyl]-1H-indol-2-yl]acetate
• CAS: 146681-76-7
• 化学式: C₂₇H₂₈N₂O₂
• 分子量: 412.532
• InChiKey: GBPMCTIIVNIKNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以87%的产率得到2-<(methoxycarbonyl)methyl>-3-<2-(N^b-benzylamino)ethyl>indole
  参考文献：
  名称：

  Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates

  摘要：

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.

  DOI：

  10.1021/jo00078a029
• 作为产物：
  描述：

  N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine 在 盐酸 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate
  参考文献：
  名称：

  Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (.+-.)-vincadifformine, (.+-.)-tabersonine, and (.+-.)-oxotabersonine

  摘要：

  Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

  DOI：

  10.1021/jo00058a025

文献信息

• 6,7,14,15-Tetrahydro[1,5]diazocino[1,2-a:6,5-a′]diindole. Synthesis of a novel pentacyclic ring system
  作者：Kittisak Sripha、Darius Paul Zlotos

  DOI：10.1016/s0040-4020(02)01530-2

  日期：2003.1

  structures for potent allosteric enhancers of antagonist binding to muscarinic M2 receptors, the first representative of a novel heterocyclic ring system, 6,7,14,15-tetrahydro[1,5]diazocino[1,2-a:6,5-a′]diindole, has been synthesized. The new pentacyclic ring skeleton is obtained from [3-(2-dibenzylaminoethyl)indol-2-yl]-acetic acid methyl ester in three steps.

  为了寻找与毒蕈碱M 2受体结合的强效变构拮抗剂拮抗剂的新的前导结构，新型杂环系统的第一个代表是6,7,14,15-四氢[1,5]重氮基[1,2- a ]已经合成了：6,5- a ']二吲哚。新的五环骨架是由[3-（2-二苄基氨基乙基）吲哚-2-基]-乙酸甲酯分三步获得的。
• Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates
  作者：Rodney L. Parsons、Jeffrey D. Berk、Martin E. Kuehne

  DOI：10.1021/jo00078a029

  日期：1993.12

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.
• Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (.+-.)-vincadifformine, (.+-.)-tabersonine, and (.+-.)-oxotabersonine
  作者：Gyorgy Kalaus、Istvan Greiner、Maria Kajtar-Peredy、Janos Brlik、Lajos Szabo、Csaba Szantay

  DOI：10.1021/jo00058a025

  日期：1993.3

  Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.