(3-苯基-1H-吲哚-2-基)乙酸甲酯 | 1039106-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: (3-苯基-1H-吲哚-2-基)乙酸甲酯
• 英文名称: (3-phenyl-1H-indol-2-yl)acetic acid methyl ester
• 英文别名: Methyl 3-phenyl-2-indolylacetate；methyl 2-(3-phenyl-1H-indol-2-yl)acetate
• CAS: 1039106-27-8
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: XQXYIMQEPCJQFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯基-1H-吲哚 、 溴乙酸甲酯 在 disodium hydrogenphosphate 、 [4,4′-di-tert-butyl-2,2′-bipyridine]bis[5-methyl-2-(4-methyl-2pyridinyl)phenyl]iridium(III) hexafluorophosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以90%的产率得到(3-苯基-1H-吲哚-2-基)乙酸甲酯
  参考文献：
  名称：

  色胺醇和色胺通过CH官能化的光化学α-羧烷基化。

  摘要：

  已经开发了在可见光照射下通过CH键的官能化使色酚和色胺的α-羧烷基化的方法。该光化学策略在Ir（iii）光催化剂的催化下并与吲哚衍生物偶联，活化了α-溴代烷基羧酸酯的C-Br键以提供以碳为中心的自由基。该方法显示出宽泛的官能团耐受性和优异的区域选择性，并应用于后期功能化和含吲哚杂种的制备。

  DOI：

  10.1039/d0cc00847h

文献信息

• Versatile Synthesis of Quinoline-3-Carboxylic Esters and Indol-2-Acetic Esters by Palladium-Catalyzed Carbonylation of 1-(2-Aminoaryl)-2-Yn-1-Ols
  作者：Bartolo Gabriele、Raffaella Mancuso、Giuseppe Salerno、Elvira Lupinacci、Giuseppe Ruffolo、Mirco Costa

  DOI：10.1021/jo8006495

  日期：2008.7.1

  1-(2-Aminoaryl)-2-yn-1-ols, easily obtained by the Grignard reaction between 1-(2-aminoaryl)ketones and alkynylmagnesium bromides, were subjected to carbonylative conditions in the presence of the PdI2-KI catalytic system, in the presence and in the absence of an external oxidant. Under oxidative conditions (80 arm of a 4:1 mixture of CO-air, in MeOH as the solvent at 100 degrees C and in the presence of 2 mol % of PdI2 and 20 mol % of KI), 1-(2-aminoaryl)-2-yn-1-ols bearing a primary amino group were selectively converted into quinoline-3-carboxylic esters in fair to good yields [45-70%, based on starting 1-(2-aminoaryl)ketones], ensuing from 6-endo-dig cyclization followed by dehydration and oxidative methoxycarbonylation. On the other hand, indol-2-acetic esters, deriving from 5-exo-dig cyclization followed by dehydrating methoxycarbonylation, were selectively obtained in moderate to good yields [42-88%, based on starting 1-(2-aminoaryl)ketones] under nonoxidative conditions (90 arm of CO, in MeOH as the solvent at 100 degrees C and in the presence of 2 mol % of PdI2 and 20 mol % of KI), in the case of 1-(2-aminoaryl)-2-yn-1-ols bearing either a primary or secondary amino group and substituted with a bulky group on the triple bond.