oleic acid N-benzyl-N-methylamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: oleic acid N-benzyl-N-methylamide
• 英文别名: (Z)-N-benzyl-N-methyloctadec-9-enamide
• 化学式: C₂₆H₄₃NO
• 分子量: 385.634
• InChiKey: WQHMTPDLSWJHNS-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  oleic acid N-benzyl-N-methylamide 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 、 1,1,3,3-四甲基二硅氧烷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以93%的产率得到N-benzyl-N-methyloleylamine
  参考文献：
  名称：

  Practical Access to Amines by Platinum-Catalyzed Reduction of Carboxamides with Hydrosilanes: Synergy of Dual Si−H Groups Leads to High Efficiency and Selectivity

  摘要：

  The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions The rate of the reaction is dependent on the distance of two Si-H groups, 1,1,3,3-tetramethyidisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, C=C, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.

  DOI：

  10.1021/ja9055307
• 作为产物：
  描述：

  油酸 、 N-甲基苄胺 在 三甲基乙酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到oleic acid N-benzyl-N-methylamide
  参考文献：
  名称：

  Dual Si–H effects in platinum-catalyzed silane reduction of carboxamides leading to a practical synthetic process of tertiary-amines involving self-encapsulation of the catalyst species into the insoluble silicone resin formed

  摘要：

  Combination of commercially available platinum catalysts with siloxanes containing more than two Si-H groups is found to be an efficient catalyst system for the reduction of carboxamides to amines. In particular, facile removal of silicon and platinum residues from the product can be achieved by the use of polymethylhydrosiloxanes as reducing reagents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.165

文献信息

• Practical Access to Amines by Platinum-Catalyzed Reduction of Carboxamides with Hydrosilanes: Synergy of Dual Si−H Groups Leads to High Efficiency and Selectivity
  作者：Shiori Hanada、Emi Tsutsumi、Yukihiro Motoyama、Hideo Nagashima

  DOI：10.1021/ja9055307

  日期：2009.10.21

  The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions The rate of the reaction is dependent on the distance of two Si-H groups, 1,1,3,3-tetramethyidisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, C=C, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.
• Dual Si–H effects in platinum-catalyzed silane reduction of carboxamides leading to a practical synthetic process of tertiary-amines involving self-encapsulation of the catalyst species into the insoluble silicone resin formed
  作者：Shiori Hanada、Yukihiro Motoyama、Hideo Nagashima

  DOI：10.1016/j.tetlet.2006.06.165

  日期：2006.8

  Combination of commercially available platinum catalysts with siloxanes containing more than two Si-H groups is found to be an efficient catalyst system for the reduction of carboxamides to amines. In particular, facile removal of silicon and platinum residues from the product can be achieved by the use of polymethylhydrosiloxanes as reducing reagents. (c) 2006 Elsevier Ltd. All rights reserved.