2-[N-(tert-butoxycarbonyl)-N-(2-trifluoromethylallyl)amino]pent-4-enoic acid methyl ester

• 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: 2-[N-(tert-butoxycarbonyl)-N-(2-trifluoromethylallyl)amino]pent-4-enoic acid methyl ester
• 英文别名: Methyl 2-[(2-methylpropan-2-yl)oxycarbonyl-[2-(trifluoromethyl)prop-2-enyl]amino]pent-4-enoate
• 化学式: C₁₅H₂₂F₃NO₄
• 分子量: 337.339
• InChiKey: VZLAJOIWXJJITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[N-(tert-butoxycarbonyl)-N-(2-trifluoromethylallyl)amino]pent-4-enoic acid methyl ester 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67%的产率得到5-trifluoromethyl-3,6-dihydro-2H-pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  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：

  甲基-2-Boc-氨基-4-戊烯酸 、 2-(trifluoromethyl)allyl 4-methylbenzenesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 以61%的产率得到2-[N-(tert-butoxycarbonyl)-N-(2-trifluoromethylallyl)amino]pent-4-enoic acid methyl ester
  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

文献信息

• RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles
  作者：Valeria De Matteis、Floris L. van Delft、Harald Jakobi、Stephen Lindell、Jörg Tiebes、Floris P. J. T. Rutjes

  DOI：10.1021/jo060893z

  日期：2006.9.1

  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.