2-((tert-butyldimethylsilyloxy)methyl)-N-(2-iodo-4-nitrophenyl)-N-(methoxymethyl)acrylamide | 1258864-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((tert-butyldimethylsilyloxy)methyl)-N-(2-iodo-4-nitrophenyl)-N-(methoxymethyl)acrylamide
• 英文别名: 2-[[tert-butyl(dimethyl)silyl]oxymethyl]-N-(2-iodo-4-nitrophenyl)-N-(methoxymethyl)prop-2-enamide
• CAS: 1258864-49-1
• 化学式: C₁₈H₂₇IN₂O₅Si
• 分子量: 506.413
• InChiKey: PXHRCBCLIMFCFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassiumhexacyanoferrate(II) trihydrate 、 2-((tert-butyldimethylsilyloxy)methyl)-N-(2-iodo-4-nitrophenyl)-N-(methoxymethyl)acrylamide 在 palladium diacetate 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以70%的产率得到2-(3-((tert-butyldimethylsilyloxy)methyl)-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
• 作为产物：
  描述：

  2-((tert-butyldimethylsilyloxy)methyl)-N-(2-iodo-4-nitrophenyl)acrylamide 、 氯甲基甲基醚 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以57%的产率得到2-((tert-butyldimethylsilyloxy)methyl)-N-(2-iodo-4-nitrophenyl)-N-(methoxymethyl)acrylamide
  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