(E)-1-Benzyl-2,3-dihydro-2-oxospiro(1H-indole-3,2'-oxirane)-3'-carboxylic Acid Ethyl Ester | 121195-63-9

• 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: (E)-1-Benzyl-2,3-dihydro-2-oxospiro(1H-indole-3,2'-oxirane)-3'-carboxylic Acid Ethyl Ester
• 英文别名: (±)-(trans)-ethyl 1-benzyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate；ethyl (2'S,3S)-1-benzyl-2-oxospiro[indole-3,3'-oxirane]-2'-carboxylate
• CAS: 121195-63-9；121195-64-0
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: XZMJONSGMDKAAS-APWZRJJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氯苯胺 、 (E)-1-Benzyl-2,3-dihydro-2-oxospiro(1H-indole-3,2'-oxirane)-3'-carboxylic Acid Ethyl Ester 以 水 为溶剂， 反应 5.0h， 以92%的产率得到(±)-ethyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)-2-[(4-chlorophenyl)amino] acetate
  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
• 作为产物：
  描述：

  ethyl (E)-2-(1-benzyl-2-oxoindolin-3-ylidene)acetate 在 奎宁 、 过氧化脲素 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 以92%的产率得到(E)-1-Benzyl-2,3-dihydro-2-oxospiro(1H-indole-3,2'-oxirane)-3'-carboxylic Acid Ethyl Ester
  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

• Asymmetric Organocatalyzed Epoxidation of 2-Oxoindoline-3-ylidene Acetaldehydes
  作者：Takasuke Mukaiyama、Kento Ogata、Tsuyoshi Ono、Yujiro Hayashi

  DOI：10.1002/cctc.201402811

  日期：2015.1

  The asymmetric epoxidation of 2‐oxoindoline‐3‐ylidene acetaldehydes, catalyzed by diarylprolinol silyl ether, has been developed. The reaction provides oxindole derivatives possessing chiral epoxides in good yield with good diastereoselectivity and excellent enantioselectivity.

  已开发了由二芳基脯氨醇甲硅烷基醚催化的2-氧代吲哚啉-3-亚乙基乙醛的不对称环氧化。该反应以良好的收率，良好的非对映选择性和优异的对映选择性提供了具有手性环氧化物的羟吲哚衍生物。
• 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.
• Baiocchi, Leandro; Giannangeli, Marilena, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1905 - 1909
  作者：Baiocchi, Leandro、Giannangeli, Marilena

  DOI：——

  日期：——
• Quinine as an organocatalytic dual activator for the diastereoselective synthesis of spiro-epoxyoxindoles
  作者：Mangilal Chouhan、Anang Pal、Ratnesh Sharma、Vipin A. Nair

  DOI：10.1016/j.tetlet.2013.10.115

  日期：2013.12

  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.