(2'R,3'R)-ethyl 1-benzyl-5-methoxy-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate | 1345838-27-8

• 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: (2'R,3'R)-ethyl 1-benzyl-5-methoxy-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate
• 英文别名: (±)-(trans)-ethyl 1-benzyl-5-methoxy-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate
• CAS: 1345838-27-8
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: CMHYZBJJNOCAJV-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1H-吲哚-2,3-二酮,5-甲氧基-1-(苯基甲基)- 在 potassium carbonate 、 奎宁 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.17h， 生成 (2'R,3'R)-ethyl 1-benzyl-5-methoxy-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate
  参考文献：
  名称：

  Quinine as an organocatalytic dual activator for the diastereoselective synthesis of spiro-epoxyoxindoles

  摘要：

  A highly efficient organocatalytic approach has been developed for the diastereoselective epoxidation of (E)-3-ylidene-indolin-2-one derivatives using readily available natural product quinine and urea-hydrogen peroxide (UHP) in DCM at 10 degrees C to afford trans spiro-epoxyoxindoles which were further utilized to obtain beta-hydroxy-alpha-amino esters by water mediated regioselective ring opening from the less hindered end with aniline derivatives, under sonication. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.115

文献信息

• Noncovalent Organocatalysis: A Powerful Tool for the Nucleophilic Epoxidation of α-Ylideneoxindoles
  作者：Chiara Palumbo、Giuseppe Mazzeo、Andrea Mazziotta、Augusto Gambacorta、M. Antonietta Loreto、Antonella Migliorini、Stefano Superchi、Daniela Tofani、Tecla Gasperi

  DOI：10.1021/ol202646w

  日期：2011.12.2

  A novel asymmetric nucleophilic epoxidation for alpha-ylideneoxindole esters has been successfully devised, resulting in enantioenriched spiro compounds with two new contiguous stereocenters. The employed (S)-alpha,alpha-diphenylprolinol functions as a bifunctional catalyst, creating a complex H-bond network in conjunction with a substrate and an oxidant.