(E)-ethyl 2-(1-benzyl-5-methoxy-2-oxoindolin-3-ylidene)acetate | 1190218-29-1

• 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)-ethyl 2-(1-benzyl-5-methoxy-2-oxoindolin-3-ylidene)acetate
• 英文别名: ethyl (2E)-2-(1-benzyl-5-methoxy-2-oxoindol-3-ylidene)acetate
• CAS: 1190218-29-1
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: GNNKEQLKRUVXFS-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 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：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(1-benzyl-5-methoxy-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(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
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 1H-吲哚-2,3-二酮,5-甲氧基-1-(苯基甲基)- 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到(E)-ethyl 2-(1-benzyl-5-methoxy-2-oxoindolin-3-ylidene)acetate
  参考文献：
  名称：

  Noncovalent Organocatalysis: A Powerful Tool for the Nucleophilic Epoxidation of α-Ylideneoxindoles

  摘要：

  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.

  DOI：

  10.1021/ol202646w

文献信息

• Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides
  作者：Xu Zhu、Shunsuke Chiba

  DOI：10.1039/c5cc10299e

  日期：——

  The Lewis acid-mediated conjugate addition of vinyl azides to electron-deficient alkenes led to the efficient construction of 1-pyrroline skeletons.

  Lewis酸介导的乙烯基叠氮化物与电子亏缺烯烃的共轭加成，有效地构建了1-吡咯烯骨架。
• INDOLINONE COMPOUND
  申请人：Kaku Hidetaka

  公开号：US20110009379A1

  公开（公告）日：2011-01-13

  [Problems] A compound, which is useful as an active ingredient for a pharmaceutical composition, for example a pharmaceutical composition for treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder, is provided. [Means for Solution] The present inventors have extensively studied compounds having TRPA1 channel activation activity, and confirmed that an indolinone compound has a TRPA1 channel activation activity, and thus completed the present invention. The indolinone compound of the present invention has a TRPA1 channel activation activity and can be used as an active ingredient of a pharmaceutical composition for preventing and/or treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder or the like.

  [问题] 提供一种化合物，该化合物可用作制药组合物的活性成分，例如用于治疗便秘型肠易激综合征，弛缓性便秘和/或功能性胃肠障碍的制药组合物。 [解决方案] 现有发明人广泛研究了具有TRPA1通道激活活性的化合物，并确认一种吲哚酮化合物具有TRPA1通道激活活性，从而完成了本发明。本发明的吲哚酮化合物具有TRPA1通道激活活性，可用作预防和/或治疗便秘型肠易激综合征，弛缓性便秘和/或功能性胃肠障碍等制药组合物的活性成分。
• 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.
• [EN] INDOLINONE COMPOUND<br/>[FR] COMPOSÉ D'INDOLINONE
  申请人：ASTELLAS PHARMA INC

  公开号：WO2009123080A1

  公开（公告）日：2009-10-08

  【課題】医薬組成物、例えば便秘型過敏性腸症候群、弛緩性便秘、及び／又は機能性胃腸障害の治療医薬組成物の有効成分として有用な化合物を提供する。 【解決手段】本発明者らは、TRPA1 チャネル活性化作用を有する化合物について鋭意検討し、式（１）で表されるインドリノン化合物がTRPA1 チャネル活性化作用を有することを確認し、本発明を完成した。本発明のインドリノン化合物はTRPA1 チャネル活性化作用を有し、便秘型過敏性腸症候群、弛緩性便秘、及び／又は機能性胃腸障害等の予防及び／又は治療医薬組成物の有効成分として使用しうる。式（１） （式中、 R1 は、-CO2H 又はその生物学的等価体等であり、 R２は、ヘテロ環、アリール、C3-8 シクロアルキル、-CO-C1-6 アルキル、-H、又は-C1-6 アルキル等であり、 R３は、-H、-C1-6 アルキル、ハロゲン、-NO2、-CN、又は-O-C1-6 アルキル等であり、 点線は、Z-オレフィン、又はE-オレフィン、あるいはこれらの混合物である。）
• 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.