1-benzyl-3-(4-tert-butylphenylimino)indolin-2-one | 328105-90-4

• 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: 1-benzyl-3-(4-tert-butylphenylimino)indolin-2-one
• 英文别名: 1-Benzyl-3-(4-tert-butylphenyl)iminoindol-2-one
• CAS: 328105-90-4
• 化学式: C₂₅H₂₄N₂O
• 分子量: 368.478
• InChiKey: KMWUSOGABQGKHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(4-tert-butylphenylimino)indolin-2-one 、 丁炔二酸二甲酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到tetramethyl 1-benzyl-1′-(4-tert-butylphenyl)-2-oxo-1′H-spiro-[indoline-3,2′-pyridine]-3′,4′,5′,6′-tetracarboxylate
  参考文献：
  名称：

  Selective Synthesis of Functionalized Spiro[indoline-3,2′-pyridines] and Spiro[indoline-3,4′-pyridines] by Lewis Acid Catalyzed Reactions of Acetylenedicarboxylate, Arylamines, and Isatins

  摘要：

  The functionalized spiro[indoline-3,2'-pyridine]-3',4',5',6'-tetracarboxylates were efficiently synthesized by BF3 center dot OEt2-catalyzed reactions of isatin-3-imines with acetylenedicarboxylates in methylene dichloride. Under similar conditions, the BF3 center dot OEt2-catalyzed three-component reactions of acetylenedicarboxylates, arylamines, and isatins afforded functionalized spiro[indoline-3,4'-pyridine]-2',3',5',6'-tetracarboxylates in moderate yields.

  DOI：

  10.1021/jo500144z

文献信息

• N-Heterocyclic Carbene-Catalyzed Homoenolate Additions with N-Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ-Lactam Oxindoles
  作者：Bo Zhang、Peng Feng、Li-Hui Sun、Yuxin Cui、Song Ye、Ning Jiao

  DOI：10.1002/chem.201201375

  日期：2012.7.23

  In pole position: A simple and efficient approach to spirocyclic γ‐lactam oxindoles by the N‐heterocyclic carbene catalyzed addition of homoenloate equivalents to N‐aryl isatinimines has been developed (see scheme). The use of N‐aryl isatinimines as electrophiles in the NHC‐catalyzed umpolung reaction of α,β‐unsaturated aldehydes is demonstrated for the first time.

  处于极点位置：已开发出一种简单有效的方法，通过N杂环卡宾催化的均烯酸酯等效物加成到N芳基异亚丁烯酮中来合成螺环γ-内酰胺ox（见方案）。首次证明了在NHC催化的α，β-不饱和醛的umpolung反应中使用N-芳基异亚胺作为亲电子试剂。
• Selective Synthesis of Functionalized Spiro[indoline-3,2′-pyridines] and Spiro[indoline-3,4′-pyridines] by Lewis Acid Catalyzed Reactions of Acetylenedicarboxylate, Arylamines, and Isatins
  作者：Hong Gao、Jing Sun、Chao-Guo Yan

  DOI：10.1021/jo500144z

  日期：2014.5.2

  The functionalized spiro[indoline-3,2'-pyridine]-3',4',5',6'-tetracarboxylates were efficiently synthesized by BF3 center dot OEt2-catalyzed reactions of isatin-3-imines with acetylenedicarboxylates in methylene dichloride. Under similar conditions, the BF3 center dot OEt2-catalyzed three-component reactions of acetylenedicarboxylates, arylamines, and isatins afforded functionalized spiro[indoline-3,4'-pyridine]-2',3',5',6'-tetracarboxylates in moderate yields.