4-(1H-indol-3-yl)-2-oxo-4-(4-methylphenyl)butyric acid ethyl ester | 1291091-38-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(1H-indol-3-yl)-2-oxo-4-(4-methylphenyl)butyric acid ethyl ester
• 英文别名: ethyl 4-(1H-indol-3-yl)-2-oxo-4-p-tolylbutanoate；ethyl (4R)-4-(1H-indol-3-yl)-4-(4-methylphenyl)-2-oxobutanoate
• CAS: 1291091-38-7
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: ZSPPQHISNPWOSV-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 ethyl 2-oxo-4-p-tolyl-3-butenoic ester 在 C₃₇H₂₇O₄P 作用下， 以 1,2-二氯乙烷 为溶剂， 以89.5%的产率得到4-(1H-indol-3-yl)-2-oxo-4-(4-methylphenyl)butyric acid ethyl ester
  参考文献：
  名称：

  光学活性的1,1'-螺双茚满-7,7'-二醇（SPINOL）基磷酸作为不对称有机催化的高对映选择性催化剂

  摘要：

  描述了一系列光学活性的1,1'-螺双茚满-7,7'-二醇（SPINOL）基磷酸的合成和应用。由（R）-SPINOL分三步制备这些基于SPINOL的磷酸，它们对于吲哚与醛亚胺和β，γ-不饱和α-酮酸酯的反应显示出极好的对映选择性。我们的研究为不对称有机催化工具箱提供了一系列有前途的手性磷酸。

  DOI：

  10.1021/jo200302x

文献信息

• Optically Active 1,1′-Spirobiindane-7,7′-diol (SPINOL)-Based Phosphoric Acids as Highly Enantioselective Catalysts for Asymmetric Organocatalysis
  作者：Chun-Hui Xing、Yuan-Xi Liao、Jaclynn Ng、Qiao-Sheng Hu

  DOI：10.1021/jo200302x

  日期：2011.5.20

  of optically active 1,1′-spirobiindane-7,7′-diol (SPINOL)-based phosphoric acids are described. These SPINOL-based phosphoric acids were prepared from (R)-SPINOL in three steps and exhibited excellent enantioselectivities for the reactions of indoles with aldimines and β,γ-unsaturated-α-ketoesters. Our study provides a family of promising chiral phosphoric acids to the asymmetric organocatalysis toolbox

  描述了一系列光学活性的1,1'-螺双茚满-7,7'-二醇（SPINOL）基磷酸的合成和应用。由（R）-SPINOL分三步制备这些基于SPINOL的磷酸，它们对于吲哚与醛亚胺和β，γ-不饱和α-酮酸酯的反应显示出极好的对映选择性。我们的研究为不对称有机催化工具箱提供了一系列有前途的手性磷酸。
• Phosphonium ion tagged chiral phosphoric acids and their application in Friedel–Crafts reactions of indoles
  作者：Julia Hermeke、Patrick H. Toy

  DOI：10.1016/j.tet.2011.03.105

  日期：2011.6

  The attachment of phosphonium ion phase tags to chiral binapthyl-based phosphoric acid catalysts, and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles has been studied. Placement of the tags at the 3 and 3' positions of the phosphoric acid, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6' positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily removed at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• Py-2NO ligand enabled Ni(<scp>ii</scp>)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters
  作者：Zi-Yue Chen、Xi-Rui Wang、Ke-Lan Xu、Pan Hu、You-Ping Tian、Hui-Juan Wang、Ying Zhou、Xiong-Li Liu

  DOI：10.1039/d3nj05076a

  日期：——

  development of chiral ligands to fine-tune stereocontrol in asymmetric catalysis is of great demand. To diversify the Py-2NO ligand library recently developed by our group, herein, we synthesized six new Py-2NO ligands, determined the absolute configuration via X-ray crystallographic study of ligand L1g, and applied these ligands in the Ni(II)-catalyzed asymmetric Michael addition reaction of indoles and

  开发用于微调不对称催化立体控制的手性配体的需求很大。为了丰富我们课题组最近开发的Py-2NO配体库，我们合成了6种新的Py-2NO配体，通过配体L1g的X射线晶体学研究确定了其绝对构型，并将这些配体应用于Ni( II )-催化吲哚和β,γ-不饱和α-酮酯的不对称迈克尔加成反应。在温和条件下，多种底物均获得了优异的产率（高达 93%）和高对映选择性（高达 99% ee）。此外，我们通过X射线晶体学研究发现叔胺衍生的N-氧化物产物中的C（芳基）-N（酰胺）键存在轴向手性。由于阻转异构现象的有趣特征，我们相信该反应将为轴向手性家族添加一个重要成员。