cyclohexylcarbamoyl cyanide

• 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: cyclohexylcarbamoyl cyanide
• 英文别名: 1-cyano-N-cyclohexylformamide
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: GYAYLSJOAJGMFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclohexylcarbamoyl cyanide 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以99%的产率得到(Z)-2-amino-N-cyclohexyl-2-(hydroxyimino)acetamide
  参考文献：
  名称：

  羟胺与氨基甲酰基叠氮化物和氨基甲酰基氰化物的不同反应性：羟基脲和氨基甲酰氨基肟的合成

  摘要：

  氨基甲酰基化剂氨基甲酰基叠氮化物和氨基甲酰基氰化物（又名氰基甲酰胺）以不同的方式与羟胺反应，在第一种情况下生成N-羟基脲，在氨基甲酰基氰化物的情况下，生成氨基甲酰基a肟肟衍生物。为后一种类型的化合物开发的合成方法代表了杂环结构的一种有趣的前体，可以高效地制备各种实例。在比较异丙基和苄基衍生物的实验值和计算出的13 C和15 N NMR化学位移值的基础上，提出了mid胺肟部分中双键的Z构型。

  DOI：

  10.1021/jo1014855
• 作为产物：
  描述：

  2-bromo-N-cyclohexyl-2,2-difluoroacetamide 在 sodium azide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 32.0h， 生成 cyclohexylcarbamoyl cyanide
  参考文献：
  名称：

  Interaction of α,α-difluoroazides with trivalent phosphorus compounds and triphenylantimony

  摘要：

  alpha,alpha-Difluoroazides react with triphenylantimony and various compounds of trivalent phosphorus according to the oxidative fluorination scheme. In the case of trivalent phosphorus compound the primary products are phosphazenes, phosphazides or difluorophosphoranes that may undergo further transformations to the corresponding fluorine derivatives of pentavalent phosphorus.

  DOI：

  10.1134/s1070363210080141

文献信息

• Solvent-Free Synthesis of Cyanoformamides from Carbamoyl Imidazoles
  作者：Jeremy Nugent、Sarah G. Campbell、Yen Vo、Brett D. Schwartz

  DOI：10.1002/ejoc.201700974

  日期：2017.9.15

  Secondary and tertiary cyanoformamides have been synthesized with a solvent-free approach from carbamoyl imidazoles and TMSCN. This method negates the need to use large excesses of toxic reagents and is amenable to large-scale synthesis.

  仲和叔氰基甲酰胺已由无溶剂方法由氨基甲酰基咪唑和TMSCN合成。该方法不需要使用大量过量的有毒试剂，并且适合大规模合成。
• Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine
  作者：Eduardo García-Egido、Jairo Paz、Beatriz Iglesias、Luis Muñoz

  DOI：10.1039/b912043b

  日期：——

  Treatment of primary amines with tetramethylphenylguanidine (PhTMG) and a cyanophosphonate at −10 °C under an atmosphere of carbon dioxide provides cyanoformamides in very high to excellent yields. The reaction proceeds efficiently within a short time. By-products were not detected in most runs and epimerization was not found when optically pure α-aminoesters were used as substrates. As an example, the reaction was applied to the synthesis of the marine natural product ceratinamine.

  在−10 °C的二氧化碳气氛下，采用四甲基苯基氨基脲（PhTMG）和氰基磷酸酯对一类胺进行处理，能够获得氰甲酰胺，产率非常高到优秀。该反应在短时间内高效进行。在大多数实验中未检测到副产物，且在使用光学纯的α-氨基酯作为底物时未发现表异构化。作为一个例子，该反应被应用于合成海洋天然产物ceratinamine。
• Cyanocarbonylation of Amines with 5-Tosyloxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione
  作者：Nobuya Katagiri、Minoru Ishikura、Yoshihiro Morishita、Masahiko Yamaguchi

  DOI：10.3987/com-99-s22

  日期：——

  5-Tosyloxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione (3), prepared by the reaction of 5-hydroxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione sodium salt (2) with tosyl chloride, was treated with various amines (4a-c and 6a,b) in the presence of triethylamine to give the corresponding N-cyanocarbonyl derivatives (5a-c and 7a,b). However, reaction of 3 with benzyl alcohol gave rise to the formation of dibenzyl carbonate (10).
• Reaction of 5-Hydroxyimino-1,3-dioxine-4,6-dione (Isonitroso Meldrum's Acid) with Carbodiimides to Give Parabanic Acids
  作者：Nobuya Katagiri、Yoshihiro Morishita、Chikara Kaneko

  DOI：10.3987/com-97-s58

  日期：——

  Reaction of 5-hydroxyimino-1,3-dioxine-4,6-dione (isonitroso Meldrum's Acid) with carbodiimides gave cyanoformamide derivatives in quantitative yields, which cyclized to iminoparabanic acids and parabanic acids under basic and acidic conditions, respectively.
• Interaction of α,α-difluoroazides with trivalent phosphorus compounds and triphenylantimony
  作者：S. A. Lermontov、A. G. Polivanova、S. B. Shkavrov

  DOI：10.1134/s1070363210080141

  日期：2010.8

  alpha,alpha-Difluoroazides react with triphenylantimony and various compounds of trivalent phosphorus according to the oxidative fluorination scheme. In the case of trivalent phosphorus compound the primary products are phosphazenes, phosphazides or difluorophosphoranes that may undergo further transformations to the corresponding fluorine derivatives of pentavalent phosphorus.