N-((3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(m-tolyl)methyl)-4-methylbenzenesulfonamide | 1398511-81-3

• 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: N-((3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(m-tolyl)methyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(R)-[(2S)-3,4-dichloro-5-oxo-2H-furan-2-yl]-(3-methylphenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 1398511-81-3
• 化学式: C₁₉H₁₇Cl₂NO₄S
• 分子量: 426.32
• InChiKey: MBYITAVIMCCMET-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二氯-2(5H)-呋喃酮 、 4-methyl-N-(3-methylbenzylidene)benzenesulfonamide 在 奎宁 作用下， 以 间二甲苯 为溶剂， 反应 168.0h， 以85%的产率得到
  参考文献：
  名称：

  Direct Asymmetric Vinylogous Mannich Reaction of 3,4-Dihalofuran-2(5H)-one with Aldimine Catalyzed by Quinine

  摘要：

  The direct asymmetric vinylogous Mannich reaction of 3,4-dihalofuran-2(513)-one with aldimine catalyzed by quinine was first reported, and gamma-butenolides have been obtained in excellent yield (up to 98%) and enantioselectivities (up to 95% ee). The synthetic applications of this protocol are demonstrated in the preparations of gamma-substituted amino butyrolactones and vicinal amino alcohols.

  DOI：

  10.1021/jo301115t

文献信息

• Direct Asymmetric Vinylogous Mannich Reaction of 3,4-Dihalofuran-2(5<i>H</i>)-one with Aldimine Catalyzed by Quinine
  作者：Yun-Long Guo、Jian-Fei Bai、Lin Peng、Liang-Liang Wang、Li-Na Jia、Xi-Ya Luo、Fang Tian、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1021/jo301115t

  日期：2012.9.21

  The direct asymmetric vinylogous Mannich reaction of 3,4-dihalofuran-2(513)-one with aldimine catalyzed by quinine was first reported, and gamma-butenolides have been obtained in excellent yield (up to 98%) and enantioselectivities (up to 95% ee). The synthetic applications of this protocol are demonstrated in the preparations of gamma-substituted amino butyrolactones and vicinal amino alcohols.