methyl 4-(1-methyl-1H-indol-3-yl)-2-oxo-4-phenylbutanoate | 1009647-87-3

• 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: methyl 4-(1-methyl-1H-indol-3-yl)-2-oxo-4-phenylbutanoate
• 英文别名: Methyl (s)-4-(1-methyl-1h-indol-3-yl)-2-oxo-4-phenylbutanoate；methyl (4S)-4-(1-methylindol-3-yl)-2-oxo-4-phenylbutanoate
• CAS: 1009647-87-3
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: NIVFSKOKMYTKFU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 4-(1-methyl-1H-indol-3-yl)-2-oxo-4-phenylbut-3-enoate 在 二氢吡啶 、 silver(I) acetate 、 氯化锆(IV) 、 C₄₄H₃₇O₄P 作用下， 以 二氯甲烷 为溶剂， 以99 %的产率得到methyl 4-(1-methyl-1H-indol-3-yl)-2-oxo-4-phenylbutanoate
  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

• 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。
• Highly enantioselective Friedel–Crafts alkylation of indole and pyrrole with β,γ-unsaturated α-ketoester catalyzed by chiral dicationic palladium complex
  作者：Kohsuke Aikawa、Kazuya Honda、Shunsuke Mimura、Koichi Mikami

  DOI：10.1016/j.tetlet.2011.09.006

  日期：2011.12

  The chiral dicationic Pd complexes, bearing sterically demanding diphosphine ligands as Lewis acid catalysts, are shown to catalyze the asymmetric Friedel–Crafts (F–C) alkylations of indoles and pyrroles with β,γ-unsaturated α-ketoesters, to provide the F–C alkylation products with benzylic stereocenters in high yields and enantioselectivities. The reactive chelated structure, formed by the chiral dicationic

  带有空间要求的二膦配体作为路易斯酸催化剂的手性二价Pd配合物，可以催化带有β，γ-不饱和α-酮酸酯的吲哚和吡咯的不对称Friedel-Crafts（FC）烷基化反应，从而提供F-具有苄基立体中心的C烷基化产物，收率高，对映选择性高。手性Pd络合物和亲电子试剂形成的反应性螯合结构对于在FC烷基化反应中获得高水平的不对称诱导非常重要。F–C产物可通过催化不对称烯序列容易地官能化以生成α-羟基酯。
• Asymmetric Binary Acid Catalysis: A Regioselectivity Switch between Enantioselective 1,2- and 1,4-Addition through Different Counteranions of InIII
  作者：Jian Lv、Long Zhang、Yueming Zhou、Zongxiu Nie、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/anie.201101254

  日期：2011.7.11

  You can count on the anion: Simply swapping the anions of an indium Lewis acid leads to a remarkable regioselectivity switch between asymmetric 1,2‐ and 1,4‐addition reactions. N‐protected indoles and β,γ‐unsaturated α‐keto esters gave adducts with excellent enantioselectivity (see scheme).

  您可以指望阴离子：简单地交换铟路易斯酸的阴离子会导致不对称的1,2-和1,4-加成反应之间显着的区域选择性转换。N保护的吲哚和β，γ-不饱和的α-酮酯可形成具有出色对映选择性的加合物（参见方案）。
• Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4-Additions
  作者：Magnus Rueping、Boris J. Nachtsheim、Stefan A. Moreth、Michael Bolte

  DOI：10.1002/anie.200703668

  日期：2008.1.4
• 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.