4-methoxy-α-phenylcinnamonitrile | 5432-07-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-methoxy-α-phenylcinnamonitrile
• 英文别名: 2-phenyl-3-(4-methoxyphenyl)acrylonitrile；3-(4-methoxyphenyl)-2-phenylacrylonitrile；3-(4-methoxy-phenyl)-2-phenyl-acrylonitrile；3-(4-Methoxy-phenyl)-2-phenyl-acrylonitril；4'-Methoxy-stilben-α-carbonsaeure-nitril；3-(4-Methoxyphenyl)-2-phenylprop-2-enenitrile
• CAS: 5432-07-5
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: VQADOVBGJXESGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  4-methoxy-α-phenylcinnamonitrile 在 sodium hydroxide 、 异戊醇 作用下， 生成 3-(4-methoxyphenyl)-2-phenylacrylic acid
  参考文献：
  名称：

  Bodroux, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911, vol. 153, p. 351

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Cyclohexen-1-yl)-3-(4-methoxyphenyl)prop-2-enenitrile 在 5%-palladium/activated carbon 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以53 %的产率得到4-methoxy-α-phenylcinnamonitrile
  参考文献：
  名称：

  钯催化α-环己烯取代腈脱氢生成α-芳基腈

  摘要：

  开发一种实用、廉价且无氰化物的合成 α-芳基腈的方法仍然是合成化学中的一个具有挑战性的目标。在这里，我们报告了一种合成α-芳基腈以实现这一目标的方法，通过该方法将α-环己烯基乙腈和α-环己烯基烯基腈脱氢为α-芳基腈。

  DOI：

  10.1039/d4cc00326h

文献信息

• Reaction of Amide Homologs. XII. Reaction of N-Arylmethylene-1-acylamino-1-arylmethylamine with Active Methylene Compound.
  作者：Minoru Sekiya、Keiichi Ito、Minako Saito

  DOI：10.1248/cpb.12.674

  日期：——

  1-Acylaminoarylmethylation of ethyl malonate was effected in several cases by interaction of N-arylmethylene-1-acylamino-1-arylmethylamine in refluxing toluene solution with suspended sodium hydroxide powder. Ethyl cyanoacetate, phenylacetonitrile and malononitrile formed arylmethylene derivatives under the same condition as with ethyl malonate.

  在某些情况下，乙基丙二酸的1-酰氨基芳基甲基化是通过N-芳亚甲基-1-酰氨基-1-芳甲基胺与悬浮的氢氧化钠粉末在回流的甲苯溶液中相互作用实现的。在相同条件下，乙基氰基乙酸酯、苯乙腈和丙二腈也形成了芳基亚甲基衍生物。
• Manganese Catalyzed α-Alkylation of Nitriles with Primary Alcohols
  作者：Akash Jana、C. Bal Reddy、Biplab Maji

  DOI：10.1021/acscatal.8b02998

  日期：2018.10.5

  The manganese(I) complex bearing a bidentate hydrazone ligand efficiently catalyzes the α-alkylations of nitrile using primary alcohols as alkylating agents. α-Functionalized nitriles were selectively obtained in good to excellent yields. The reaction is environmentally benign, producing water as the sole byproduct. Both benzylic and aliphatic alcohols could be used and functional groups were tolerated

  带有双齿配体的锰（I）络合物使用伯醇作为烷基化剂，可有效催化腈的α-烷基化。有选择地以高至优异的产率获得了α-官能化的腈。该反应对环境无害，产生水作为唯一的副产物。苄醇和脂族醇都可以使用，并且官能团是可容忍的。
• Thermal rearrangement of 2,3-diaryl-1-phthalimidoaziridines
  作者：Alena S. Pankova、Mariia V. Sorokina、Mikhail A. Kuznetsov

  DOI：10.1016/j.tetlet.2015.07.093

  日期：2015.9

  ziridines and 2,3-diaryl-1-phthalimidoaziridine-2-carbonitriles were found to readily undergo thermal rearrangement into imines via 1,2-migration of the phthalimido group and accompanying C–C bond cleavage. Isomerization proceeds regioselectively with preferable migration to the electron-deficient carbon atom. Interestingly, this reaction was found to predominate even in the presence of dipolarophiles

  发现2,3-二芳基-1-邻苯二甲酰亚胺基氮杂环丁烷和2,3-二芳基-1-邻苯二甲酰亚胺基氮杂环丁烷-2-腈通过邻苯二甲酰亚胺基的1,2-迁移和伴随的CC键断裂容易发生热重排成亚胺。异构化区域选择性地进行，并优选迁移至缺电子的碳原子。有趣的是，发现该反应甚至在亲偶极生物的存在下也占主导地位。
• Choline Chloride and Urea Based Eutectic Solvents: Effective Catalytic Systems for the Knoevenagel Condensation Reactions of Substituted Acetonitriles
  作者：Shuo Liu、Yuxiang Ni、Wenjing Wei、Fangli Qiu、Songlin Xu、Anguo Ying

  DOI：10.3184/174751914x13926483381319

  日期：2014.3

  The Knoevenagel condensation of aromatic aldehydes with active methylene compounds such as malononitrile, ethyl cyanoacetate, benzimidazole-2-acetonitrile and benzothiazole-2-acetonitrile proceeded very smoothly, in a reusable and cheap choline chloride and urea based deep eutectic solvents. Both reaction time and yield are satisfactory. The advantages of this catalyst are that it is readily available

  芳香醛与活性亚甲基化合物如丙二腈、氰基乙酸乙酯、苯并咪唑-2-乙腈和苯并噻唑-2-乙腈的 Knoevenagel 缩合在可重复使用且廉价的氯化胆碱和尿素基低共熔溶剂中进行得非常顺利。反应时间和收率均令人满意。这种催化剂的优点是易得、可生物降解、无毒、成本低且可回收。
• Base‐Promoted α‐Alkylation of Arylacetonitriles with Alcohols
  作者：Bivas Chandra Roy、Istikhar A. Ansari、Sk. Abdus Samim、Sabuj Kundu

  DOI：10.1002/asia.201900285

  日期：2019.7

  A practical method to synthesize α‐alkylated arylacetonitriles from arylacetonitriles and alcohols without using any expensive transition metal complexes is demonstrated here. Following this base‐catalysed sustainable procedure, various arylacetonitriles were successfully alkylated with different alcohols. The practical applicability of this protocol was extended by one‐pot synthesis of important carboxylic

  本文展示了一种从芳基乙腈和醇类合成α-烷基化芳基乙腈的实用方法，无需使用任何昂贵的过渡金属络合物。按照这种碱催化的可持续程序，各种芳基乙腈已成功地用不同的醇烷基化。通过重要的羧酸衍生物的一锅法合成扩展了该协议的实际适用性。