N-methyl-N-(1-adamantyl)formamide

• 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-methyl-N-(1-adamantyl)formamide
• 英文别名: N-(1-adamantyl)-N-methylformamide
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: JTZLKTVICVREOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  N-methyl-N-(1-adamantyl)formamide 在 sodium hydride 、 三氯氧磷 作用下， 以 mineral oil 、 苯 为溶剂， 反应 23.33h， 生成 β-[methyl(1-adamantyl)amino]acrylonitrile
  参考文献：
  名称：

  A base induced transformation of a 1,3-dimethyl-1,3-di(1-adamantyl)formamidinium salt into β-[methyl-(1-adamantyl)amino]acrylonitriles in aliphatic nitriles

  摘要：

  A novel 1,3-dimethyl-1,3-di-(1-adamantyl)formamidinium perchlorate has been prepared via the Vilsmeier-Haack reaction of N-methyl-N-(1-adamantyl)formamide and N-methyl-N-(1-adamantyl) amine in a mixture of phosphorus oxychloride and benzene. The new formamidinium salt was found to undergo addition-elimination reactions when treated with sodium hydride in acetonitrile or propionitrile solution, thereby forming the corresponding beta-[methyl(1-adamantyl)amino]acrylonitriles and N-methyl-N-(1-adamantyl) amine. The H-1 and C-13 NMR spectra and the single-crystal X-ray structure of the new formamidinium salt have been determined along with those of the related compound 1,3-di-(1-adamantyl)-1-cyanoamidine and the corresponding beta-(dialkylamino)acrylonitriles.

  DOI：

  10.3998/ark.5550190.0013.207

文献信息

• Highly efficient carbene and polycarbene catalysis of the transesterification reaction
  作者：Konstantin A. Marichev、Nikolai I. Korotkikh、Alan H. Cowley、Vagiz Sh. Saberov、Nataliya V. Glinyanaya、Gennady F. Rayenko、Oles P. Shvaika

  DOI：10.24820/ark.5550190.p010.034

  日期：——

  Highly efficient carbene and polycarbene catalysis of the transesterification reaction of ethyl benzoate in methanol has been observed and results in values of TON as high as 4000–6150 at a molar ratio of ester to methanol of 1:18 at room temperature. The most effective catalysts were found to be the individual carbenes or in situ generated carbenes, namely adamantyl and aromatic substituted cyclic

  已经观察到苯甲酸乙酯在甲醇中的酯交换反应的高效卡宾和聚卡宾催化，并且在室温下酯与甲醇的摩尔比为 1:18 时，TON 值高达 4000-6150。发现最有效的催化剂是单独的卡宾或原位生成的卡宾，即金刚烷基和芳族取代的环状化合物和聚合卡宾。这些反应都不需要使用分子筛。聚合咪唑-2-亚基催化剂用于从葵花油中高效生产生物柴油燃料。
• Regioselective electrophilic formylation—3-substituted thiophenes as a case study
  作者：Otto Meth-Cohn、Mark Ashton

  DOI：10.1016/s0040-4039(00)00254-9

  日期：2000.4

  A variety of methods for regioselective formylation have been examined and exemplified with 3-methylthiophene. Optimal yields and regioselectivity for 2-formylation were obtained with N-formylpyrrolidine (11:1) although up to a 46:1 ratio could be obtained with MeOCHCl2:TiCl4, albeit in lower yield. Optimal 5-formylation (1:1.5) was obtained when using N-formylindoline:(COCl)2.

  已经研究了多种用于区域选择性甲酰化的方法，并以3-甲基噻吩为例。用N-甲酰基吡咯烷（11：1）可获得最佳的产率和2-甲酰基化的区域选择性，尽管用MeOCHCl 2：TiCl 4可获得高达46：1的比例，尽管产率较低。当使用N-甲酰吲哚啉：（COCl）2时，获得最佳的5-甲酰化（1：1.5）。
• A base induced transformation of a 1,3-dimethyl-1,3-di(1-adamantyl)formamidinium salt into β-[methyl-(1-adamantyl)amino]acrylonitriles in aliphatic nitriles
  作者：Arthur V. Knishevitsky、Nikolai I. Korotkikh、Alan H. Cowley、Jennifer A. Moore、Kalyan V. Vasudevan、Tatyana M. Pekhtereva、Oles P. Shvaika

  DOI：10.3998/ark.5550190.0013.207

  日期：——

  A novel 1,3-dimethyl-1,3-di-(1-adamantyl)formamidinium perchlorate has been prepared via the Vilsmeier-Haack reaction of N-methyl-N-(1-adamantyl)formamide and N-methyl-N-(1-adamantyl) amine in a mixture of phosphorus oxychloride and benzene. The new formamidinium salt was found to undergo addition-elimination reactions when treated with sodium hydride in acetonitrile or propionitrile solution, thereby forming the corresponding beta-[methyl(1-adamantyl)amino]acrylonitriles and N-methyl-N-(1-adamantyl) amine. The H-1 and C-13 NMR spectra and the single-crystal X-ray structure of the new formamidinium salt have been determined along with those of the related compound 1,3-di-(1-adamantyl)-1-cyanoamidine and the corresponding beta-(dialkylamino)acrylonitriles.