(+)-4-(1H-indol-3-yl)-2-oxo-4-(4-bromophenyl)butyric acid methyl ester | 1201664-61-0

• 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-bromophenyl)butyric acid methyl ester
• 英文别名: (S)-4-(1H-indol-3-yl)-2-oxo-4-(4-bromophenyl)butyric acid methyl ester；methyl (4S)-4-(4-bromophenyl)-4-(1H-indol-3-yl)-2-oxobutanoate
• CAS: 1201664-61-0
• 化学式: C₁₉H₁₆BrNO₃
• 分子量: 386.245
• InChiKey: BELFYZQLXWNIMG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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 、 4-(4-bromophenyl)-2-oxo-3-butenoic acid methyl ester 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90%的产率得到(+)-4-(1H-indol-3-yl)-2-oxo-4-(4-bromophenyl)butyric 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

• Enantioselective Friedel–Crafts Alkylation of Indoles with β,γ-Unsaturated α-Ketoesters Catalyzed by New Copper(I) Catalysts
  作者：Shibo Yu、Qihang Cai、Chao Wang、Jiaqi Hou、Jiemian Liang、Zilin Jiao、Chao Yao、Yue-Ming Li

  DOI：10.1021/acs.joc.2c02749

  日期：2023.3.3

  stabilizing the reaction intermediate and enhancing the stereoselectivity of the reactions. The desired products can be obtained in up to 98% yield at 99% enantiomeric excess. The same high enantioselectivity can be observed when the reaction is carried in a gram scale, indicating a good scalability of the catalyst system in enantioselective Friedel–Crafts alkylation of different indoles with β,γ-unsaturated

  新型 Cu(I) 催化剂可有效地对多种吲哚与不同的 β,γ-不饱和 α-酮酯进行对映选择性 Friedel-Crafts 烷基化。一项控制研究表明，这种催化剂系统对空气的敏感性较低，反应可以在没有特殊照顾的情况下进行，例如手套箱操作或无湿气/无氧条件。初步计算结果表明，底物和催化剂之间存在π-π堆积，这种相互作用似乎起到了稳定反应中间体和提高反应立体选择性的作用。在 99% 的对映体过量下，可以获得高达 98% 的收率。当反应以克规模进行时，可以观察到相同的高对映选择性，
• 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.