4-(1H-indol-3-yl)-2-oxo-4-(4-methoxyphenyl)butyric acid methyl ester | 1201664-85-8

• 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: 4-(1H-indol-3-yl)-2-oxo-4-(4-methoxyphenyl)butyric acid methyl ester
• 英文别名: methyl (R)-4-(1H-indol-3-yl)-4-(4-methoxyphenyl)-2-oxobutanoate
• CAS: 1201664-85-8
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: YGLATLKJHQERJA-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 4-(1H-indol-3-yl)-4-(4-methoxyphenyl)-2-oxobut-3-enoate 在 二氢吡啶 、 C₄₄H₁₉F₁₀O₄P 作用下， 以 二氯甲烷 为溶剂， 以75 %的产率得到4-(1H-indol-3-yl)-2-oxo-4-(4-methoxyphenyl)butyric acid methyl ester
  参考文献：
  名称：

  不对称二元酸催化：对映选择性共轭氢化物还原中的可切换对映选择性

  摘要：

  金属离子从 Zr(IV) 到 Fe(III) 的交换导致二元酸催化的共轭氢化物还原的对映选择性发生变化。在 Hantzsch 酯存在下，γ-吲哚基 β,γ-不饱和 α-酮酯可以分别还原为所需的 ( S )- 或 ( R )- 产物，具有良好至优异的对映选择性（高达 98% ee） .

  DOI：

  10.1021/acs.orglett.2c04087

文献信息

• Asymmetric Latent Carbocation Catalysis with Chiral Trityl Phosphate
  作者：Jian Lv、Qichao Zhang、Xingren Zhong、Sanzhong Luo

  DOI：10.1021/jacs.5b11085

  日期：2015.12.16

  Stable carbocations such as tritylium ions have been widely explored as organic Lewis acid catalysts and reagents in organic synthesis. However, achieving asymmetric carbocation catalysis remains elusive ever since they were first identified over one century ago. The challenges mainly come from their limited compatibility, scarcity of chiral carbocations, as well as the extremely low barrier to racemization

  稳定的碳正离子如三苯甲基离子已被广泛用作有机合成中的有机路易斯酸催化剂和试剂。然而，自从一个多世纪前首次发现它们以来，实现不对称碳正离子催化仍然难以实现。挑战主要来自它们有限的相容性、手性碳正离子的稀缺性以及极低的手性碳正离子外消旋化障碍。我们在这里报告了不对称碳正离子催化的潜在概念。在该策略中，手性磷酸三苯甲基酯用作碳阳离子前体，在温和的外部刺激（例如酸、氢键、极性底物）下容易发生离子解离，形成具有催化活性的手性离子对，用于底物活化和手性诱导。
• AgAsF₆/Sm(OTf)₃ Promoted Reversal of Enantioselectivity for the Asymmetric Friedel−Crafts Alkylations of Indoles with β,γ-Unsaturated α-Ketoesters
  作者：Yanling Liu、Deju Shang、Xin Zhou、Yin Zhu、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/ol902587t

  日期：2010.1.1

  The first example of central metal controlled reversal of enantioselectivity in asymmetric Friedel-Crafts alkylation of Indoles and beta,gamma-unsaturated alpha-ketoesters has been developed. Using the same chiral starting material derived N,N'-dioxides 1 a and 1 b as ligands, various indole esters 4 were obtained In good to excellent yields and enantioselectivities. The reaction also featured mild reaction conditions and remarkably low catalyst loading (down to 0.01 mol %).
• 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.