N-methyl-N-phenyl-carbamoyl cyanide | 99839-93-7

• 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: N-methyl-N-phenyl-carbamoyl cyanide
• 英文别名: N-methyl-N-phenylcarbamoyl cyanide；N-methyl-N-phenylcyanoformamide；methyl(phenyl)carbamoyl cyanide；N-methyl-N-phenylcyanamide；methyl-phenyl-oxalamonitrile；Methyl-phenyl-oxalamonitril；1-cyano-N-methyl-N-phenylformamide
• CAS: 99839-93-7
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: MKCUJZZBPTWSKW-UHFFFAOYSA-N

物化性质

• 熔点：
  61-63 °C
• 沸点：
  250.1±23.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硫酸 、 N-methyl-N-phenyl-carbamoyl cyanide 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  DE515542

  摘要：

  公开号：
• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 氧气 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 N-methyl-N-phenyl-carbamoyl cyanide
  参考文献：
  名称：

  Solution and Solid-State Photochemistry of 2-Anilino-5-phenyl-2,4-pentadienenitriles

  摘要：

  2-(N-Methylanilino)-5-phenyl-2,4-pentadienenitrile (3) undergoes either isomerization or oxidative cleavage at the 2,3-double bond upon irradiation in solution, whereas it dimerizes in a regiospecific manner to give the [2 + 2] cycloaddition product 12 upon irradiation in the solid state. From the fluorescence spectra and semiempirical calculation, the excited state of 3 is proposed to be a twist intramolecular charge transfer species. The X-ray analysis indicates that molecules 3b orient appropriately with a reasonable distance for the [2 + 2] cycloaddition in the solid state. The distance between C2 and C3' is 525 pm, the longest distance known in solid-state [2 + 2] cycloadditions. 2-(N-Methyl-p-bromoanilino)-5-phenyl-2,4-pentadienenitrile (4) shows behavior similar to that of 3 in the solution and solid-state photochemistry, whereas analogs 7-10 having nitro substituents on the 5-phenyl rings do not dimerize upon irradiation in the solid state. Semiempirical calculation of the electronic structures is used to interprete the discrepancy of reactivity.

  DOI：

  10.1021/jo00098a037

文献信息

• Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-<i>N</i>-arylamides under an Oxygen Atmosphere
  作者：Shunsuke Chiba、Line Zhang、Jian-Yuan Lee

  DOI：10.1021/ja1027327

  日期：2010.6.2

  copper-catalyzed reaction of alpha-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C=O bonds. The

  发现α-叠氮基-N-芳基酰胺的铜催化反应在氧气氛下进行以提供氮杂螺环己二烯酮。本转化是通过从 α-叠氮基-N-芳基酰胺脱氮形成亚胺基铜物种以及它们与酰胺氮上的分子内苯环的亚氨基铜化，然后连续形成 C=O 键来进行的。初步调查显示，分子氧是实现本催化环化的先决条件，并且发现 O(2) 的氧原子之一被纳入环己二烯酮部分。
• The synthesis of cyanoformamides <i>via</i> a CsF-promoted decyanation/oxidation cascade of 2-dialkylamino-malononitriles
  作者：Lin-Sheng Lei、Cao-Gen Xue、Xue-Tao Xu、Da-Ping Jin、Shao-Hua Wang、Wen Bao、Huan Liang、Kun Zhang、Abdullah M. Asiri

  DOI：10.1039/c9ob00510b

  日期：——

  A mild and efficient method for the synthesis of cyanoformamides from N,N-disubstituted aminomalononitriles with CsF as the promoter has been developed. This method features a wide substrate scope and high reaction efficiency, and will facilitate corresponding cyanoformamide-based biological studies and synthetic methodology development.

  已经开发了一种温和而有效的方法，该方法以CsF为促进剂，从N，N-二取代的氨基丙二腈合成氰基甲酰胺。该方法具有广泛的底物范围和高的反应效率，并将促进相应的基于氰基甲酰胺的生物学研究和合成方法的发展。
• 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 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds
  作者：Nivesh Kumar、Santanu Ghosh、Subhajit Bhunia、Alakesh Bisai

  DOI：10.3762/bjoc.12.111

  日期：——

  benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of beta-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for

  经由“无过渡金属”的分子内脱氢偶联（IDC），已经完成了在假苄基位置带有全碳季中心的各种2-氧吲哚的合成。通过使用KOt-Bu催化β-N-芳基酰胺酯与烷基卤化物的一锅C-烷基化，然后脱氢偶联，通过形成碳-碳键来进行2-氧吲哚部分的构建。实验证据表明该反应朝向自由基介导的途径。
• Electrochemical Synthesis of Cyanoformamides from Trichloroacetonitrile and Secondary Amines Mediated by the B₁₂ Derivative
  作者：Mohammad Moniruzzaman、Yoshio Yano、Toshikazu Ono、Kenji Imamura、Yoshihito Shiota、Kazunari Yoshizawa、Yoshio Hisaeda、Hisashi Shimakoshi

  DOI：10.1021/acs.joc.1c00837

  日期：2021.11.19

  The B12 derivative, heptamethyl cobyrinate, -mediated electrochemical synthesis of cyanoformamides has been developed. Aerobic oxygenation of the carbon-centered radical initiated in situ generation of the reactive acyl chloride intermediate, which led to cyanoformamides in the presence of an amine. This one-pot and scalable synthetic method has been demonstrated with 41 examples up to 94% yields with

  已经开发了B 12衍生物，七甲基钴酸，介导的氰基甲酰胺的电化学合成。碳中心自由基的有氧氧化引发了反应性酰氯中间体的原位生成，这在胺的存在下产生了氰基甲酰胺。这种一锅法且可扩展的合成方法已通过 41 个示例得到证明，其中 21 种新化合物的产率高达 94%。基于DFT计算提出了由B 12衍生物介导的电解机理。