(E)-3-styryl-1-methyl-1H-indole-2-carboxylic acid | 1306764-67-9

• 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: (E)-3-styryl-1-methyl-1H-indole-2-carboxylic acid
• CAS: 1306764-67-9
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: UTTWFUCPPRRECK-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 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：
  0.06
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-3-styryl-1-methyl-1H-indole-2-carboxylic acid 、 L-苯丙氨醇 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到(S,E)-3-styryl-N-(1-hydroxy-3-phenylpropan-2-yl)-1-methyl-1H-indole-2-carboxamide
  参考文献：
  名称：

  Indole-olefin-oxazoline (IndOlefOx)-ligands: synthesis and utilization in asymmetric Rh-catalyzed conjugate addition

  摘要：

  The synthesis and utility of novel indole-olefin-oxazoline (IndOlefOx)-ligands are described. The use of these ligands was demonstrated in rhodium catalyzed asymmetric conjugate additions between 2-cyclopentenone, 2-cyclohexenone, and 2-cycloheptenone with different boron reagents with good yields and enantioselectivities of up to 94%. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.020
• 作为产物：
  描述：

  ethyl (E)-3-styryl-1-methyl-indole-2-caboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(E)-3-styryl-1-methyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Indole-olefin-oxazoline (IndOlefOx)-ligands: synthesis and utilization in asymmetric Rh-catalyzed conjugate addition

  摘要：

  The synthesis and utility of novel indole-olefin-oxazoline (IndOlefOx)-ligands are described. The use of these ligands was demonstrated in rhodium catalyzed asymmetric conjugate additions between 2-cyclopentenone, 2-cyclohexenone, and 2-cycloheptenone with different boron reagents with good yields and enantioselectivities of up to 94%. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.020

文献信息

• Cross‐Dehydrogenative Coupling/Annulation of Arene Carboxylic Acids and Alkenes in Water with Ruthenium(II) Catalyst and Air
  作者：Anup Mandal、Bholanath Garai、Suman Dana、Ratnadeep Bera、Mahiuddin Baidya

  DOI：10.1002/asia.202001087

  日期：2020.12

  cross‐dehydrogenative coupling of arene carboxylic acids with olefins is reported with ruthenium(II) catalyst employing air and water as green oxidant and solvent, respectively. It offers a robust synthesis of valuable phthalide molecules. A one‐pot sequential strategy is also disclosed to access Heck‐type products that are apparently difficult to make directly from arene carboxylic acids.

  据报道，钌（II）催化剂分别使用空气和水作为绿色氧化剂和溶剂，将芳烃羧酸与烯烃进行交叉脱氢偶联。它提供了有价值的邻苯二甲酸酯分子的可靠合成方法。还公开了一种单罐顺序策略，以访问显然难以直接从芳烃羧酸制备的Heck型产品。
• Ru-Catalyzed (<i>E</i>)-Specific <i>ortho</i>-C–H Alkenylation of Arenecarboxylic Acids by Coupling with Alkenyl Bromides
  作者：Zhiyong Hu、Florian Belitz、Guodong Zhang、Florian Papp、Lukas J. Gooßen

  DOI：10.1021/acs.orglett.1c00956

  日期：2021.5.7

  alkenyl bromides, (E)-configured vinyl arenes or dienes are formed exclusively. Mechanistic studies show that this selectivity is achieved because the (E)-configured alkenyl bromides undergo a smooth coupling, whereas the (Z)-isomers are rapidly eliminated with the formation of alkynes.

  在[对-异丙基）RuCl 2 ] 2的存在下，（E）-构型的烯基溴化物与芳族羧酸盐偶合形成邻-乙烯基苯甲酸。这种C–H乙烯基化无需任何活化的膦配体就可以高产率进行，并且具有出色的官能团耐受性。从烯基溴化物的常见（E / Z）混合物开始，仅形成（E）构型的乙烯基芳烃或二烯。机理研究表明，实现这种选择性的原因是，（E）-构型的烯基溴化物经历了平滑的偶联，而（Z异构体会随着炔烃的形成而迅速消除。