tert-butyl 1-(methoxymethyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-5-ylcarbamate | 1258864-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 1-(methoxymethyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-5-ylcarbamate
• 英文别名: tert-butyl N-[1-(methoxymethyl)-2-oxospiro[indole-3,3'-pyrrolidine]-5-yl]carbamate
• CAS: 1258864-56-0
• 化学式: C₁₈H₂₅N₃O₄
• 分子量: 347.414
• InChiKey: VDDWXQPOBTVURJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-(methoxymethyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-5-ylcarbamate 、 环丙基甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 1'-(cyclopropanecarbonyl)-1-(methoxymethyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-5-ylcarbamate
  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：

  allyl 5-(tert-butoxycarbonylamino)-1-(methoxymethyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate 在 四(三苯基膦)钯 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到tert-butyl 1-(methoxymethyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-5-ylcarbamate
  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.