2-{N-[(5-chloro-2-methoxyphenyl)sulfonyl]-N-(2-trifluoromethylallyl)amino}-N-(4-chloro-3-trifluoromethylbenzyl)pent-4-enamide | 913563-91-4

• 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-{N-[(5-chloro-2-methoxyphenyl)sulfonyl]-N-(2-trifluoromethylallyl)amino}-N-(4-chloro-3-trifluoromethylbenzyl)pent-4-enamide
• 英文别名: 2-[(5-chloro-2-methoxyphenyl)sulfonyl-[2-(trifluoromethyl)prop-2-enyl]amino]-N-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]pent-4-enamide
• CAS: 913563-91-4
• 化学式: C₂₄H₂₂Cl₂F₆N₂O₄S
• 分子量: 619.412
• InChiKey: BXFUIKWDXPDQFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-{N-[(5-chloro-2-methoxyphenyl)sulfonyl]-N-(2-trifluoromethylallyl)amino}-N-(4-chloro-3-trifluoromethylbenzyl)pent-4-enamide 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到1-(5-chloro-2-methoxybenzenesulfonyl)-5-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid 4-chloro-3-trifluoromethylbenzylamide
  参考文献：
  名称：

  RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles

  摘要：

  A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.

  DOI：

  10.1021/jo060893z
• 作为产物：
  描述：

  DL-2-氨基-4-戊烯酸 在 三甲基氯硅烷 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 生成 2-{N-[(5-chloro-2-methoxyphenyl)sulfonyl]-N-(2-trifluoromethylallyl)amino}-N-(4-chloro-3-trifluoromethylbenzyl)pent-4-enamide
  参考文献：
  名称：

  RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles

  摘要：

  A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.

  DOI：

  10.1021/jo060893z