N-(4-chlorophenyl)-N-methyl-2-methylidene-4-[(4-methylphenyl)sulfonylamino]butanamide | 1247768-01-9

• 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: N-(4-chlorophenyl)-N-methyl-2-methylidene-4-[(4-methylphenyl)sulfonylamino]butanamide
• CAS: 1247768-01-9
• 化学式: C₁₉H₂₁ClN₂O₃S
• 分子量: 392.906
• InChiKey: CRJBMHMZBNWDDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-N-methyl-2-methylidene-4-[(4-methylphenyl)sulfonylamino]butanamide 在 碘苯二乙酸 、 palladium dichloride 作用下， 以 乙腈 为溶剂， 以58%的产率得到5-chloro-1-methyl-1'-tosylspiro[indoline-3,3'-pyrrolidin]-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles

  摘要：

  A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivatives involving concomitant direct C H functionalization and C X bond formation was developed By simply changing the reaction conditions (solvent and catalyst), either 3,3'-disubstituted oxindole or spirooxindole was accessible from the same starting material.

  DOI：

  10.1021/ol101778c

文献信息

• Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles
  作者：Hai-Long Wei、Tiffany Piou、Jeremy Dufour、Luc Neuville、Jieping Zhu

  DOI：10.1021/ol2005243

  日期：2011.5.6

  Cyclisative carbo-iodination of N-alkyl-N-arylacrylamide derivatives (3) in the presence of PhI(OAc)(2)/I-2 afforded functionalized 3-(iodomethyl)-3-substituted-indolin-2-ones (4) in good to excellent yields. With a suitably functionalized linear amide, spirooxindole 8 was prepared in a one-pot fashion via a sequence of iodo-arylation followed by an in situ base-promoted intramolecular S(N)2 reaction.