(-)-4-(5-methoxy-1H-indol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester | 1398242-81-3

• 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: (-)-4-(5-methoxy-1H-indol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester
• 英文别名: (S)-4-(5-methoxy-1H-indol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester；methyl (S)-4-(5-methoxy-1H-indol-3-yl)-2-oxo-4-phenylbutanoate；methyl (4S)-4-(5-methoxy-1H-indol-3-yl)-2-oxo-4-phenylbutanoate
• CAS: 1398242-81-3
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: RWDMUCMZHLGFTE-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 methyl 4-phenyl-2-oxo-3-butenoate 在 bis[(S)-4-phenyloxazoline-2-yl]-2-(thienyl)-ethene 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(-)-4-(5-methoxy-1H-indol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester
  参考文献：
  名称：

  吲哚的对映体选择性高的Friedel-Crafts烷基化和与β-吡咯，通过heteroarylidene拴双恶唑啉铜配合物催化的γ-不饱和的α-酮酯。

  摘要：

  简单和廉价的手性催化剂，heteroarylidene拴PH-双（恶唑啉）-Cu（OTF）（2），可有效地催化的吲哚并吡咯与β-，γ-不饱和的α-酮酯的不对称FC烷基化。在高达> 99％ee的获得了3-吲哚基的加合物。此外，2-吡咯基的加合物在高达92％ee的首次得以实现。

  DOI：

  10.1039/c2cc34803a

文献信息

• Polystyrene-supported cu(II)-R-Box as recyclable catalyst in asymmetric Friedel–Crafts reaction
  作者：V. G. Desyatkin、M. V. Anokhin、V. O. Rodionov、I. P. Beletskaya

  DOI：10.1134/s1070428016120010

  日期：2016.12

  complex of copper(II) trifluoromethanesulfonate with chiral isopropyl bis(oxazoline) ligand (i-Pr-Box) was immobilized on accessible and inexpensive Merrifield resin according to a “click” procedure. The resulting catalyst showed high efficiency and recyclability in the asymmetric Friedel–Crafts alkylation of indole and its derivatives. The catalyst can be recycled five times without appreciable loss in

  根据“点击”程序，将三氟甲磺酸铜（II）与手性异丙基双（恶唑啉）配体（i-Pr-Box）的配合物固定在可及且廉价的Merrifield树脂上。所得催化剂在吲哚及其衍生物的不对称Friedel-Crafts烷基化反应中显示出高效率和可回收性。催化剂可以循环使用五次，而活性和对映选择性没有明显损失。
• Asymmetric Binary-Acid Catalysis with Chiral Phosphoric Acid and MgF₂: Catalytic Enantioselective Friedel−Crafts Reactions of β,γ-Unsaturated α-Ketoesters
  作者：Jian Lv、Xin Li、Long Zhong、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1021/ol1000928

  日期：2010.3.5

  A unique binary chiral phosphoric acid 1a/MgF2 catalyst that enables effective catalysis of asymmetric Friedel−Crafts reactions of phenols with up to 82% yield and >99% ee is presented. A dramatic synergistic effect has been observed in the combinations of two types of acids, wherein a highly active binary-acid catalyst can be generated from two individually inert acids.

  介绍了一种独特的二元手性磷酸1a / MgF 2催化剂，该催化剂能够以高达82％的收率和> 99％ee的效率有效催化酚的不对称Friedel-Crafts反应。在两种类型的酸的组合中已经观察到显着的协同作用，其中可以由两种单独的惰性酸产生高活性的二元酸催化剂。
• Enantioselective Friedel–Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline–Zn(OTf)2 complexes
  作者：Sheng-Jian Jia、Da-Ming Du

  DOI：10.1016/j.tetasy.2014.05.011

  日期：2014.7

  Enantioselective Friedel-Crafts alkylation reactions of indoles with beta,gamma-unsaturated alpha-ketoesters catalyzed by novel chiral C-2-symmetric squaramide-linked bisoxazoline-Zn(OTf)(2) complexes were investigated. The corresponding indole ketoesters were obtained in good to excellent yields (up to 98%) and with high enantioselectivities (up to 94% ee). This is the first report on the use of chiral squaramide-linked bisoxazoline SQBOX in a catalytic enanitioselective Friedel-Crafts alkylation reaction. (C) 2014 Elsevier Ltd. All rights reserved.