2-[(triphenylphosphoranylidene)amino]benzonitrile | 139308-38-6

• 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: 2-[(triphenylphosphoranylidene)amino]benzonitrile
• 英文别名: 2-<(triphenylphosphoranylidene)amino>benzonitrile；2-[(Triphenyl-lambda~5~-phosphanylidene)amino]benzonitrile；2-[(triphenyl-λ5-phosphanylidene)amino]benzonitrile
• CAS: 139308-38-6
• 化学式: C₂₅H₁₉N₂P
• mdl: MFCD05260208
• 分子量: 378.413
• InChiKey: KCEOOWGQUWFXAD-UHFFFAOYSA-N

物化性质

• 沸点：
  571.7±52.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(triphenylphosphoranylidene)amino]benzonitrile 在 sodium carbonate 作用下， 反应 1.0h， 生成 2-氨基苯甲腈
  参考文献：
  名称：

  Regioselective Condensation of Alkylidenephosphoranes with Bifunctionalized Compounds: New Approach to the Synthesis of FusedO- andN-Heterocycles

  摘要：

  A series of fused pyran- (similar to 40% yield) and furan- (similar to 20% yield) derivatives were regioselectively prepared from the reactions of 5,6-difur-2'y1-3-oxo-2,3-dihydropyridazin-4-carbonitrile with ester- and keto phosphorus ylides, whereas new ylides were obtained, in addition to fused furans, in almost equal yields (33%) from the reaction of the same substrate with cyanomethylene(triphenyl)phosphorane. However application of such Wittig reagents on 2[(benzylidene)amino]-benzonitrile afforded, in all cases, 4-hydroxyquinalines in a similar to 42% yield as major products. Moreover; 2-[(triphenylphosphoranylidene)amino] benzonitrile, with the corresponding alkene, was also isolated a side products.

  DOI：

  10.1080/104265090921092
• 作为产物：
  描述：

  2-氨基苯甲腈 、 二溴三苯基膦 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到2-[(triphenylphosphoranylidene)amino]benzonitrile
  参考文献：
  名称：

  An Easy Entry into 2-Halo-3-aryl-4(3H)-quinazoliniminium Halides from Heteroenyne-allenes

  摘要：

  An efficient three-step synthesis of 2-halo-3-aryl-4(3H)-quinazoliniminium halides from commercially available materials is described. Upon reaction with hydrogen halides, generated in situ from a Lewis acid (MX) and trace water, a variety of easily accessible heteroenyne-allenes underwent facile intramolecular cyclization to afford the title compounds in good yields. The method is highly versatile and provides a general way to construct quinazoliniminium ring systems with a variety of different substitutions.

  DOI：

  10.1021/ol201372n

文献信息

• A simple aza wittig-mediated pyrimidine annulation reaction
  作者：Edward C. Taylor、Mona Patel

  DOI：10.1002/jhet.5570280810

  日期：1991.12

  Treatment of heterocyclic o-aminonitriles and o-aminoesters 1a-5a with dibromotriphenylphosphorane gives iminophosphoranes 1b-5b which undergo a facile aza-Wittig reaction at room temperature with phenyl isocyanate to provide the carbodiimides 1c-5c. Treatment of the latter intermediates with ammonia leads to intramolecular ring closure of the initially formed guanidines to provide the fused 4-aminopyrimidines

  用二溴三苯基膦处理杂环邻氨基腈和邻氨基酯1a-5a得到亚氨基正膦1b-5b，其在室温下与异氰酸苯酯进行简单的氮杂-维蒂希反应以提供碳二亚胺1c-5c。用氨处理后面的中间体导致最初形成的胍的分子内闭环，以提供稠合的4-氨基嘧啶和4（3H）-嘧啶酮1d-Sd。
• An Easy Entry into 2-Halo-3-aryl-4(3<i>H</i>)-quinazoliniminium Halides from Heteroenyne-allenes
  作者：Vijaya Kumar Naganaboina、Kusum Lata Chandra、John Desper、Sundeep Rayat

  DOI：10.1021/ol201372n

  日期：2011.7.15

  An efficient three-step synthesis of 2-halo-3-aryl-4(3H)-quinazoliniminium halides from commercially available materials is described. Upon reaction with hydrogen halides, generated in situ from a Lewis acid (MX) and trace water, a variety of easily accessible heteroenyne-allenes underwent facile intramolecular cyclization to afford the title compounds in good yields. The method is highly versatile and provides a general way to construct quinazoliniminium ring systems with a variety of different substitutions.
• One-Pot Cascade Approach to Phenanthridine-Fused Quinazoliniminiums from Heteroenyne-Allenes
  作者：Olajide E. Alawode、Vijaya Kumar Naganaboina、Thakshila Liyanage、John Desper、Sundeep Rayat

  DOI：10.1021/ol500314x

  日期：2014.3.7

  A one-pot cascade method to obtain functionalized phenanthridine-fused quinazoliniminiums from a variety of heteroenyne-allenes is described. This protocol involves formation of C-N and C-C bonds in a single step in the presence of a Lewis acid and trace water to afford pentacyclic title compounds in moderate to good yields.
• Regioselective Condensation of Alkylidenephosphoranes with Bifunctionalized Compounds: New Approach to the Synthesis of Fused<i>O</i>- and<i>N</i>-Heterocycles
  作者：Wafaa M. Abdou、Neven A. F. Ganoub、Amin F. M. Fahmy、Abeer A. M. Shaddy

  DOI：10.1080/104265090921092

  日期：2005.10

  A series of fused pyran- (similar to 40% yield) and furan- (similar to 20% yield) derivatives were regioselectively prepared from the reactions of 5,6-difur-2'y1-3-oxo-2,3-dihydropyridazin-4-carbonitrile with ester- and keto phosphorus ylides, whereas new ylides were obtained, in addition to fused furans, in almost equal yields (33%) from the reaction of the same substrate with cyanomethylene(triphenyl)phosphorane. However application of such Wittig reagents on 2[(benzylidene)amino]-benzonitrile afforded, in all cases, 4-hydroxyquinalines in a similar to 42% yield as major products. Moreover; 2-[(triphenylphosphoranylidene)amino] benzonitrile, with the corresponding alkene, was also isolated a side products.