2-(3-(hydroxymethyl)-1-(methoxymethyl)-5-nitro-2-oxoindolin-3-yl)acetonitrile | 1258864-92-4

• 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-(hydroxymethyl)-1-(methoxymethyl)-5-nitro-2-oxoindolin-3-yl)acetonitrile
• 英文别名: 2-[3-(Hydroxymethyl)-1-(methoxymethyl)-5-nitro-2-oxoindol-3-yl]acetonitrile；2-[3-(hydroxymethyl)-1-(methoxymethyl)-5-nitro-2-oxoindol-3-yl]acetonitrile
• CAS: 1258864-92-4
• 化学式: C₁₃H₁₃N₃O₅
• 分子量: 291.263
• InChiKey: SUNCRAFSTWJVNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-(hydroxymethyl)-1-(methoxymethyl)-5-nitro-2-oxoindolin-3-yl)acetonitrile 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到[3-(cyanomethyl)-1-(methoxymethyl)-5-nitro-2-oxoindolin-3-yl]methyl methanesulfonate
  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：

  2-(3-((tert-butyldimethylsilyloxy)methyl)-1-(methoxymethyl)-5-nitro-2-oxoindolin-3-yl)acetonitrile 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到2-(3-(hydroxymethyl)-1-(methoxymethyl)-5-nitro-2-oxoindolin-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.