ethyl (1-carboethoxy-1H-indol-3-yl)cyanoacetate | 55747-25-6

• 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: ethyl (1-carboethoxy-1H-indol-3-yl)cyanoacetate
• 英文别名: 3-(cyano-ethoxycarbonyl-methyl)-indole-1-carboxylic acid ethyl ester；2-cyano-2-(1-ethoxycarbonyl-indol-3-yl)-acetic acid ethyl ester；ethyl 3-(1-cyano-2-ethoxy-2-oxoethyl)indole-1-carboxylate
• CAS: 55747-25-6
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: CCZMDXSEJTUNCP-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±53.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (1-carboethoxy-1H-indol-3-yl)cyanoacetate 在 Raney Ni (W-4) sodium hydroxide 、 氢气 作用下， 反应 8.0h， 生成 3-amino-2-(3-indolyl)propionic acid
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022
• 作为产物：
  描述：

  吲哚-3-乙腈 、 碳酸二乙酯 在 sodium 作用下， 反应 1.5h， 以56%的产率得到ethyl (1-carboethoxy-1H-indol-3-yl)cyanoacetate
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022

文献信息

• A Versatile Approach for the Synthesis of 8H-Thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-Acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and Its Derivatives: A Novel Synthesis of Intermediate (1-Acetyl-1H-indol-3-
  作者：Valeriya S. Velezheva、Alexander Yu. Lepyoshkin、Konstantin F. Turchin、Irina N. Fedorova、Alexander S. Peregudov、Patrick J. Brennan

  DOI：10.1002/jhet.960

  日期：2013.3

  the synthesis of new 2‐amino‐3‐cyano/alkoxycarbonyl‐8H‐thieno[2,3‐b]indoles 5 and another one for the synthesis of 2‐N,N‐dialkylamino‐3‐cyano/aryl‐8H‐thieno[2,3‐b]indoles 16, based either on acetylindoxyl 1 and (1‐acetyl‐1H‐indol‐3‐yl)malononitrile/cyanoacetates 14 or 2‐bromoacetylindoxyl 2 transformations. A new, simple, rapid, and efficient method for the synthesis of valuable key intermediate ma

  我们报告了两种合成新的2-氨基-3-氰基/烷氧基羰基-8H-噻吩并[2,3 - b]吲哚5的方法，另一种用于合成2 - N，N-二烷基氨基-3-氰基的方法。 / aryl-8H-thieno [2,3-b]吲哚16，基于乙酰吲哚基1和（1-乙酰基-1H-吲哚-3-基）丙二腈/氰基乙酸酯14或2-溴乙酰基吲哚基2转化。一种新的，简单，快速而有效的方法，用于合成基于乙酰吲哚酚1的重要关键中间体丙二腈/氰基乙酸酯14已经开发了在三乙胺存在下与丙二腈或氰基乙酸酯缩合的方法。许多用于硫代乙酰胺的制备合成步骤6，1- acetylthioisatin 8，和2,2-二取代的indoxyls 13噻吩并[2,3-B]吲哚的合成过程中已被详细阐述。硫代乙酰胺6已被证明是对结核分枝杆菌H 37 Rv有活性的新型药物，其抑制浓度范围在5至21μg/ mL之间。
• Morales-Rios, Martha S.; Bucio-Vasquez, Ma. Alvina; Joseph-Nathan, Pedro, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 953 - 956
  作者：Morales-Rios, Martha S.、Bucio-Vasquez, Ma. Alvina、Joseph-Nathan, Pedro

  DOI：——

  日期：——