diphenylcyanamide | 27779-01-7

• 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: diphenylcyanamide
• CAS: 27779-01-7
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: NWJGNHCFEPMCCT-UHFFFAOYSA-N

物化性质

• 熔点：
  73.5°C
• 沸点：
  320.68°C (rough estimate)
• 密度：
  1.1579 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diphenylcyanamide 在 甲醇 、 羟胺 作用下， 生成 1,1-Diphenyl-2-hydroguanidine
  参考文献：
  名称：

  v.Braun; Schwarz, Chemische Berichte, 1903, vol. 36, p. 3661

  摘要：

  DOI：
• 作为产物：
  描述：

  (4E)-4-(diphenylhydrazinylidene)-3-methyl-1,2-oxazol-5-one 生成 diphenylcyanamide
  参考文献：
  名称：

  WENTRUP C.; WINTER H.-W., J. ORG. CHEM., 1981, 46, NO 5, 1045-1046

  摘要：

  DOI：

文献信息

• Chemoselective Reactions of Tellurium Tetraethoxide towards Thioamides and Amides
  作者：Kazushi Omote、Yoshio Aso、Tetsuo Otsubo、Fumio Ogura

  DOI：10.1246/bcsj.67.1759

  日期：1994.6

  Tellurium tetraethoxide reacts with primary thioamides at room temperature, forming nitriles in high yields. On the other hand, the reactions with amides are largely temperature-dependent, giving predominantly esters at 80 °C and nitriles at a higher temperature. Similarly, tellurium tetraethoxide readily induces the C–N bond cleavage of ureas to give carbamates and amines.

  四乙氧基碲在室温下与伯硫酰胺反应，高效生成腈。另一方面，四乙氧基碲与酰胺的反应很大程度上依赖于温度，在80°C主要生成酯，而在更高温度下生成腈。同样，四乙氧基碲容易引发尿素中的C-N键断裂，生成氨基甲酸酯和胺。
• 5‐(Cyano)dibenzothiophenium Triflate: A Sulfur‐Based Reagent for Electrophilic Cyanation and Cyanocyclizations
  作者：Xiangdong Li、Christopher Golz、Manuel Alcarazo

  DOI：10.1002/anie.201904557

  日期：2019.7.8

  and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not

  报道了通过用Tf 2 O活化二苯并[b，d]噻吩-5-氧化物并随后与TMSCN反应制备的5-（氰基）二苯并噻吩三氟甲磺酸盐9的合成，并评估了其作为亲电氰化试剂的反应性。9促进了亲电氰化的可扩展制备，易于处理和广泛的底物范围其中包括胺，硫醇，甲硅烷基烯醇醚，烯烃，富电子（杂）芳烃和聚芳烃，说明了该试剂的合成潜力。重要的是，转移过程不需要试剂的路易斯酸活化。我们在此另外报告了仿生氰基环化级联反应，该反应不是典型的亲电子氰化试剂所促进的，证明了9具有引发挑战性转化的优异能力。
• MILD AND SELECTIVE OXIDATIONS WITH POLYSTYRENE-BOUND DIARYL SELENOXIDE
  作者：Nan Xing Hu、Yoshio Aso、Tetsuo Otsubo、Fumio Ogura

  DOI：10.1246/cl.1985.603

  日期：1985.5.5

  Polystyrene-bound diaryl selenoxide is shown to behave as a mild oxidizing agent for thiol to disulfide, sulfide to sulfoxide, phosphine to phosphine oxide, and hydroguinone to benzoguinone. In add...

  聚苯乙烯结合的二芳基硒氧化物被证明是硫醇生成二硫化物、硫化物生成亚砜、膦生成氧化膦和氢醌生成苯醌的温和氧化剂。另外...
• 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。
• A NEW SYNTHESIS OF ALKYL FLUORIDES: THE PYROLYSIS OF 2-ALKYLPSEUDOURONIUM FLUORIDES AND FLUOROBORATES
  作者：J. H. Amin、J. Newton、F. L. M. Pattison

  DOI：10.1139/v65-442

  日期：1965.12.1

  The pyrolysis of 2-alkylpseudouronium fluorides and fluoroborates at approximately 185° gave alkyl fluorides in yields of up to 77%. The method is most useful for the preparation of primary alkyl fluorides; attempts to prepare secondary fluorides, such as cyclohexyl fluoride, gave the corresponding alkenes.

  2-烷基伪氟鎓氟化物和氟硼酸盐在大约 185° 下的热解得到了产率高达 77% 的烷基氟化物。该方法最适用于制备伯烷基氟化物；尝试制备二级氟化物，如环己基氟，得到了相应的烯烃。