methylcyanamide | 4674-68-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methylcyanamide
• 英文别名: Methylcyanamid；N-methylcyanamide
• CAS: 4674-68-4
• 化学式: C₂H₄N₂
• mdl: MFCD16767882
• 分子量: 56.0672
• InChiKey: MCLITRXWHZUNCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  -50--40 °C
• 沸点：
  38.8±23.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methylcyanamide 以 乙醇 为溶剂， 反应 12.0h， 生成 Trimethyl-isomelamin
  参考文献：
  名称：

  异三聚氰胺和异氰脲酸酯的合成及其生物学评价。

  摘要：

  溴化氰（1）与伯胺（2a-p），包括芳基甲胺（2-1-p）的反应，得到了相应的氰酰胺（3a-p）。3a-p的三聚得到1,3,5-三取代的2,4,6-三亚氨基六氢-1,3,5-三嗪（异三聚氰胺）（4a-p），将其用盐酸处理，得到相应的1,3 ，5-三取代的2,4,6-三氧六氢-1,3,5-三嗪（异氰脲酸酯）（5a-c，f）和1,3,5-三取代的2-亚氨基-4,6-二氧六氢-1,3 ，5-三嗪（5b'-e'）。对4a-p，5a-c，f和5b'-e'进行了生物学评估，其中一些化合物显示支气管扩张药和正性肌力活性。

  DOI：

  10.1248/cpb.44.2314
• 作为产物：
  描述：

  1-methyl-5-tetrazolyl lithium 生成 methylcyanamide
  参考文献：
  名称：

  Application of 5-lithiotetrazoles in organic synthesis

  摘要：

  Lithiation of I-benzyl and 1-p-methoxybenzyltetrazole at the 5-position with n-butyllithium followed by treatment with electrophiles gave functionalized 1-benzylic tetrazoles, which were converted into the 1-unsubstituted derivatives by debenzylation.

  DOI：

  10.1016/0040-4039(95)00117-u

文献信息

• [EN] PYRROLOPYRIMIDINES AS JANUS KINASE INHIBITORS<br/>[FR] PYRROLOPYRIMIDINES EN TANT QU'INHIBITEURS DE KINASE JANUS
  申请人：MERCK SHARP & DOHME

  公开号：WO2013085802A1

  公开（公告）日：2013-06-13

  The instant invention provides compounds of formula I which are JAK3 inhibitors. Specifically, the compounds of formula I are pyrrolo[2,3-d]pyrimidine derivative compounds. The instant invention also provides methods of treating JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer, by administering the pyrrolo[2,3-d]pyrimidine-derivative compounds of formula I.

  这项即时发明提供了化合物I的公式，这些化合物是JAK3抑制剂。具体来说，化合物I的公式是吡咯并[2,3-d]嘧啶衍生物化合物。该即时发明还提供了治疗JAK介导疾病，如类风湿性关节炎、哮喘、慢性阻塞性肺病和癌症的方法，通过给予公式I的吡咯并[2,3-d]嘧啶衍生物化合物。
• Copper-Catalyzed One-Pot Synthesis of Unsymmetrical Arylurea Derivatives via Tandem Reaction of Diaryliodonium Salts with <i>N</i>-Arylcyanamide
  作者：Pengfei Li、Guolin Cheng、Hong Zhang、Xianxiang Xu、Jingyuan Gao、Xiuling Cui

  DOI：10.1021/jo501334u

  日期：2014.9.5

  efficient “one-pot” approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples

  已经提出了一种有效的“一锅法”，用于从N-芳基氰酰胺和二芳基碘鎓盐中制备多种取代的尿素。该两步过程涉及仲胺与二芳基碘鎓的弱碱促进的化学选择性芳基化和第二仲芳基碘鎓的铜催化的N-芳基氰酰胺的亲核加成。对于29个实施例，以高达91％的收率获得了各种不对称的芳基脲。
• [EN] THERAPEUTIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS THÉRAPEUTIQUES ET MÉTHODES D'UTILISATION ASSOCIÉS
  申请人：GENENTECH INC

  公开号：WO2021097110A1

  公开（公告）日：2021-05-20

  The invention relates to compounds and methods of using said compounds, as well as pharmaceutical compositions containing such compounds, for treating diseases and conditions mediated by TEAD, such as cancer.

  该发明涉及化合物及其使用方法，以及含有这些化合物的药物组合物，用于治疗由TEAD介导的疾病和状况，如癌症。
• Syntheses of arylcyanotriazenes and related compounds.
  作者：MASAYUKI TANNO、SHOKO SUEYOSHI、SHOZO KAMIYA

  DOI：10.1248/cpb.30.3125

  日期：——

  1-Aryl-3-cyanotriazene potassium salts (IIa-j) were synthesized by treating the corresponding arylazides (Ia-j) with potassium cyanide. When IIa-j were treated with dimethyl sulfate in the presence of dicyclohexyl-18-crown ether-6 (18-crown-6), methylation occurred at N1 and N3 of the triazeno group. The resulting two isomers, 1-aryl-3-cyano-1-methyltriazenes (IIIa-j) and 1-aryl-3-cyano-3-methyltriazenes (IVa-f) were all separable by means of chromatography on silica gel. However, several of the 3-isomers (IVg-j) were not isolated. On the other hand, the direct alkylation of arylcyanotriazene potassium salts (IIa, c, e) with dimethyl sulfate in methanol gave only the 1-methyl derivatives, 1-aryl-3-cyano-1-methyltriazenes (IIIa, c, e). The alkylated positions in these products were determined by chemical and spectral studies. A clear correlation between the Hammett constants and the 13C-nuclear magnetic resonance (13C-NMR) chemical shifts of the nitrile carbons of (1-aryl-3-cyano) methyltriazenes (IIIa-j, IVa-f) was obtained.

  1-芳基-3-氰基三氮烯钾盐（IIa-j）是通过将相应的芳基叠氮化合物（Ia-j）与氰化钾反应合成的。在二环己基-18-冠醚-6（18-冠-6）的存在下，将IIa-j与硫酸二甲酯反应，会在三氮烯基团的N1和N3位置发生甲基化。所得的两种异构体，即1-芳基-3-氰基-1-甲基三氮烯（IIIa-j）和1-芳基-3-氰基-3-甲基三氮烯（IVa-f），均可通过硅胶色谱法分离。然而，几种3-异构体（IVg-j）未能被分离出来。另一方面，将芳基氰基三氮烯钾盐（IIa、c、e）在甲醇中直接与硫酸二甲酯烷基化，仅得到1-甲基衍生物，即1-芳基-3-氰基-1-甲基三氮烯（IIIa、c、e）。这些产品中的烷基化位置是通过化学和光谱研究确定的。得到了Hammett常数与（1-芳基-3-氰基）甲基三氮烯（IIIa-j、IVa-f）的氰基碳的13C核磁共振（13C-NMR）化学位移之间的明显相关性。
• Phenyltriazole derivative and insecticide
  申请人：Kumiai Chemical Industry Co., Ltd.

  公开号：US04925864A1

  公开（公告）日：1990-05-15

  A phenyltriazole derivative of the formula: ##STR1## wherein X is a halogen atom, an alkyl group, a halogen-substituted alkyl group, an alkoxy group, a nitro group, a phenoxy group, an amino group, a cyano group, a 1-pyrrolyl group or a halogen-substituted alkoxy group, Y is a C.sub.2 -C.sub.6 alkyl group which may be substituted by halogen, alkoxy, alkylthio, alkylsulfonyl, alkoxycarbonyl or carbamoyl, a methyl-substituted cycloalkyl group, an alkenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group or a 2-methyl-1,3-dithiolan-2-yl group, Z is a hydrogen atom, a halogen atom, a halogen-substituted alkyl group, an alkoxyalkyl group, an alkenyloxyalkyl group, a methyl group, an alkylsulfinyl group, an alkylsulfonyl group, a phenyl group, a ##STR2## group, wherein each of R.sup.1 and R.sup.2 which may be the same or different is a hydrogen atom, an alkyl group, an alkoxy group, an acyl group, an amino group, a phenyl group, an alkenyl group, an alkynyl group, a dimethylcarbamoyl group, an alkoxycarbonyl group, a trichloromethylthio group or an alkylsulfonyl group which may be substituted by halogen, or R.sup.1 and R.sup.2 form together with the adjacent nitrogen atom, a hetero ring, or a ##STR3## group wherein R.sup.3 is a hydrogen atom of an alkylthio group and R.sup.4 is an alkylthio group or an alkoxy group, and n is an integer of 0 to 5.

  一个苯基三唑衍生物的化学式为：其中X是卤素原子、烷基、卤素取代的烷基、烷氧基、硝基、苯氧基、氨基、氰基、1-吡咯基或卤素取代的烷氧基，Y是C.sub.2-C.sub.6烷基，可以被卤素、烷氧基、烷基硫醚、烷基磺酰基、烷氧羰基或氨基取代，甲基取代的环烷基、烯基、C.sub.1-C.sub.4烷基亚砜基或2-甲基-1,3-二硫代环戊烷基，Z是氢原子、卤素原子、卤素取代的烷基、烷氧基烷基、烯烷氧基烷基、甲基、烷基亚砜基、烷基磺酰基、苯基、或其中的R.sup.1和R.sup.2（可能相同也可能不同）是氢原子、烷基、烷氧基、酰基、氨基、苯基、烯基、炔基、二甲基氨基羰基、烷氧羰基、三氯甲基硫基或可以被卤素取代的烷基磺酰基，或者R.sup.1和R.sup.2与相邻氮原子一起形成一个杂环，或其中R.sup.3是氢原子或烷基硫基，R.sup.4是烷基硫基或烷氧基，n是0到5之间的整数。