2-[3-((1,3-dioxolan-2-yl)methyl)-5-chloro-2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-3-yl]acetonitrile | 1258864-69-5

• 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-[3-((1,3-dioxolan-2-yl)methyl)-5-chloro-2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-3-yl]acetonitrile
• 英文别名: 2-[5-Chloro-3-(1,3-dioxolan-2-ylmethyl)-2-oxo-1-(2-trimethylsilylethoxymethyl)indol-3-yl]acetonitrile；2-[5-chloro-3-(1,3-dioxolan-2-ylmethyl)-2-oxo-1-(2-trimethylsilylethoxymethyl)indol-3-yl]acetonitrile
• CAS: 1258864-69-5
• 化学式: C₂₀H₂₇ClN₂O₄Si
• 分子量: 422.984
• InChiKey: PXBGFXNPJXCDEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-((1,3-dioxolan-2-yl)methyl)-5-chloro-2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-3-yl]acetonitrile 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到2-[5-chloro-2-oxo-3-(2-oxoethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-3-yl]acetonitrile
  参考文献：
  名称：

  Palladium-catalyzed domino Heck/cyanation: synthesis of 3-cyanomethyloxindoles and their conversion to spirooxoindoles

  摘要：

  3'-Alkyl-3-cyanomethyloxindoles, prepared by a palladium-catalyzed domino Heck/cyanation, were efficiently converted to spiropyrrolidinyl-, spiropiperidinyl- and spirocyclopropyl-oxindoles. The so-obtained spirooxindoles bearing three diversity points were further functionalized via selective N-acylation, N-alkylation, N-sulfonylation, SNAr reaction and Buchwald-Hartwig N-arylation reaction to reach diverse set of heterocycles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.056
• 作为产物：
  描述：

  potassiumhexacyanoferrate(II) trihydrate 、 2-((1,3-dioxolan-2-yl)methyl)-N-(4-chloro-2-iodophenyl)-N-[(2-(trimethylsilyl)ethoxy)methyl]-acrylamide 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以68%的产率得到2-[3-((1,3-dioxolan-2-yl)methyl)-5-chloro-2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-3-yl]acetonitrile
  参考文献：
  名称：

  Palladium-catalyzed domino Heck/cyanation: synthesis of 3-cyanomethyloxindoles and their conversion to spirooxoindoles

  摘要：

  3'-Alkyl-3-cyanomethyloxindoles, prepared by a palladium-catalyzed domino Heck/cyanation, were efficiently converted to spiropyrrolidinyl-, spiropiperidinyl- and spirocyclopropyl-oxindoles. The so-obtained spirooxindoles bearing three diversity points were further functionalized via selective N-acylation, N-alkylation, N-sulfonylation, SNAr reaction and Buchwald-Hartwig N-arylation reaction to reach diverse set of heterocycles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.056

文献信息

• Palladium-catalyzed domino Heck/cyanation: synthesis of 3-cyanomethyloxindoles and their conversion to spirooxoindoles
  作者：Stéphanie Jaegli、Jean-Pierre Vors、Luc Neuville、Jieping Zhu

  DOI：10.1016/j.tet.2010.09.056

  日期：2010.11

  3'-Alkyl-3-cyanomethyloxindoles, prepared by a palladium-catalyzed domino Heck/cyanation, were efficiently converted to spiropyrrolidinyl-, spiropiperidinyl- and spirocyclopropyl-oxindoles. The so-obtained spirooxindoles bearing three diversity points were further functionalized via selective N-acylation, N-alkylation, N-sulfonylation, SNAr reaction and Buchwald-Hartwig N-arylation reaction to reach diverse set of heterocycles. (C) 2010 Elsevier Ltd. All rights reserved.