1-(4-Chloro-phenyl)-1H-indole-2-carboxylic acid ethyl ester | 754199-21-8

• 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: 1-(4-Chloro-phenyl)-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 1-(4-chlorophenyl)indole-2-carboxylate
• CAS: 754199-21-8
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: MJEPPWVEDIPHHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-Chloro-phenyl)-1H-indole-2-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-(4-chlorophenyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of neutral P1 substituents

  摘要：

  A series of novel, highly potent 2-carboxyindole-based factor Xa inhibitors is described. Structural requirements for neutral ligands, which bind in the S1 pocket of factor Xa were investigated with the 2-carboxyindole scaffold. This privileged fragment assembly approach yielded a set of equipotent, selective inhibitors with structurally diverse neutral P1 substituents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.020
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 、 4-氯苯硼酸 在 吡啶 、 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 1-(4-Chloro-phenyl)-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of neutral P1 substituents

  摘要：

  A series of novel, highly potent 2-carboxyindole-based factor Xa inhibitors is described. Structural requirements for neutral ligands, which bind in the S1 pocket of factor Xa were investigated with the 2-carboxyindole scaffold. This privileged fragment assembly approach yielded a set of equipotent, selective inhibitors with structurally diverse neutral P1 substituents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.020

文献信息

• Construction of N–C Axial Chirality through Atroposelective C–H Olefination of <i>N</i>-Arylindoles by Palladium/Amino Acid Cooperative Catalysis
  作者：Jitan Zhang、Qiaoqiao Xu、Jiaping Wu、Jian Fan、Meihua Xie

  DOI：10.1021/acs.orglett.9b02243

  日期：2019.8.16

  Direct construction of N–C axial chirality via Pd-catalyzed atroposelective C–H olefination of N-arylindoles is reported. The crucial role of chiral amino acid as a cocatalyst in the regio- and stereocontrol has been disclosed. In this reaction, a wide range of arylindoles and functional alkenes could be well tolerated. Moreover, the practicality and synthetic value of this process were demonstrated

  据报道，通过Pd催化的N-芳基吲哚的对映体选择性CH烯化反应，可以直接构建Nc轴向手性。已经公开了手性氨基酸在区域和立体控制中作为助催化剂的关键作用。在该反应中，可以很好地耐受各种芳基吲哚和官能烯烃。而且，该方法的实用性和综合价值通过产品的多样化者和简单的改造得到了证明。