(E)-4-((2-phenylhydrazono)methyl)benzonitrile | 100726-23-6

• 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: (E)-4-((2-phenylhydrazono)methyl)benzonitrile
• 英文别名: (E)-4-[(2-phenylhydrazono)methyl]benzonitrile；p-cyanobenzaldehyde phenylhydrazone；4-[(E)-(phenylhydrazono)methyl]benzonitrile；4-[(E)-(phenylhydrazinylidene)methyl]benzonitrile
• CAS: 100726-23-6
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: CXCWFSDDYJMHAM-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (E)-4-((2-phenylhydrazono)methyl)benzonitrile 在 potassium carbonate 作用下， 以 乙腈 、 苯 为溶剂， 反应 5.0h， 生成 (Z)-1,4-diphenyl-2-(phenylamino)but-2-ene-1,4-dione
  参考文献：
  名称：

  Photochemical transformations of (E)-1-(2'-arylidene-1'-phenylhydrazinyl)-1,2-dibenzoylalkenes

  摘要：

  DOI：

  10.1021/jo00361a006
• 作为产物：
  描述：

  苯肼 、 4-氰基苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-4-((2-phenylhydrazono)methyl)benzonitrile
  参考文献：
  名称：

  离子配对催化在对映选择性加成腙到Ñ -acyldihydropyrrole衍生物†

  摘要：

  我们已经证明，基于二氢吡咯烯酰胺衍生物可作为手性季的高效前体起作用Ñ下布朗斯台德酸催化的是经历与腙反应-acyliminium盐，后者参与作为掩蔽亲核羰基等价物。优化的方法以优异的产率提供了多种对映体纯的α-取代的脯氨酸衍生物，甚至与产生两个连续立体中心的二取代的β-烯酰胺相容。

  DOI：

  10.1039/c8cc05311a

文献信息

• An efficient five-component synthesis of thioether containing dihydropyrano[2,3-c]pyrazoles: a green domino strategy
  作者：Vediyappan Ramesh、Sivakumar Shanmugam、Natarajan Savitha Devi

  DOI：10.1039/c6nj02313d

  日期：——

  An efficient route for the synthesis of novel thioether containing dihydropyrano[2,3-c]pyrazoles has been accomplished via a solvent-free, catalyst-free, one-pot, five component domino strategy. This synthetic approach offers several advantages such as an easy work-up, no need for purification techniques and a short reaction time with good atom economy and high yields of the products (81–86%).

  通过无溶剂，无催化剂，一锅，五组分多米诺骨牌策略，已经成功地完成了一种新型的含有二氢吡喃并[2,3- c ]吡唑的硫醚合成方法。这种合成方法具有许多优点，例如后处理容易，无需纯化技术，反应时间短，原子经济性好，产物收率高（81-86％）。
• <i>sp</i> 2-C-H Acetoxylation of Diversely Substituted (<i>E</i> )-1-(Arylmethylene)-2-phenylhydrazines Using PhI(OAc)₂ as Acetoxy Source at Ambient Conditions
  作者：Goutam Brahmachari、Indrajit Karmakar

  DOI：10.1002/ejoc.201900994

  日期：2019.9.15

  It's Simple! Catalyst‐ and additive‐free regioselective direct sp2 C–H acetoxylation of biologically interesting aldehyde hydrazones to access a new series of hydrazone acetates has been achieved. The reaction proceeds at ambient temperature employing PIDA as an acetoxy source.

  很简单！已实现了对生物感兴趣的乙的无催化剂和无添加剂的区域选择性直接sp 2 C–H乙酰化反应，从而获得了一系列新的acetate乙酸盐。使用PIDA作为乙酰氧基源，反应在环境温度下进行。
• Ion-pairing catalysis in the enantioselective addition of hydrazones to <i>N</i>-acyldihydropyrrole derivatives
  作者：Nagore Zabaleta、Uxue Uria、Efraim Reyes、Luisa Carrillo、Jose L. Vicario

  DOI：10.1039/c8cc05311a

  日期：——

  demonstrated that dihydropyrrole-based enamide derivatives can act as efficient precursors of chiral quaternary N-acyliminium salts under Brønsted acid catalysis that undergo reactions with hydrazones, the latter participating as masked nucleophilic carbonyl group equivalents. The optimized methodology provides a variety of enantiopure α-substituted proline derivatives in excellent yields, being even compatible

  我们已经证明，基于二氢吡咯烯酰胺衍生物可作为手性季的高效前体起作用Ñ下布朗斯台德酸催化的是经历与腙反应-acyliminium盐，后者参与作为掩蔽亲核羰基等价物。优化的方法以优异的产率提供了多种对映体纯的α-取代的脯氨酸衍生物，甚至与产生两个连续立体中心的二取代的β-烯酰胺相容。
• Efficient Synthesis of Fully Substituted and Diversely Functionalized Pyrazoles through <i>p</i>‐TSA Catalyzed One‐Pot Condensation of Cyclic <i>β</i>‐Diketones, Arylglyoxals and Arylhydrazones
  作者：Arun Dhurey、Subhro Mandal、Animesh Pramanik

  DOI：10.1002/ejoc.202300770

  日期：2023.10.21

  An acid catalyzed one-pot condensation of readily available cyclic β-diketones, arylglyoxals and arylhydrazones produces a library of diversely functionalized pyrazole derivatives in excellent yield under metal-catalyst-free benign conditions.

  容易获得的环状β-二酮、芳基乙二醛和芳基腙的酸催化一锅缩合反应在无金属催化剂的良性条件下以优异的产率产生了多种官能化的吡唑衍生物库。
• Organocatalytic asymmetric hydroarylation of o-hydroxyl styrenes via remote activation of phenylhydrazones
  作者：Wei Dai、Han Lu、Xiao-Li Jiang、Ting-Ting Gao、Feng Shi

  DOI：10.1016/j.tetasy.2014.12.009

  日期：2015.2

  The first catalytic asymmetric styrene hydroarylation reaction has been established via the enantioselective Friedel-Crafts alkylations of phenylhydrazones with o-hydroxyl styrenes under the catalysis of a chiral phosphoric acid as an organocatalyst, leading to the construction of a chiral 1,1-diarylethane scaffold with high enantioselectivity (up to 89% ee). The investigation on the activation mode suggested that the two reactants, o-hydroxyl styrenes and phenylhydrazones, were simultaneously activated by the catalyst via multiple hydrogen-bonds. The remote activation of the hydrazone functionality by a dual hydrogen-bonding interaction with the catalyst contributed greatly to the hydroarylation reaction of the o-hydroxyl styrenes. (C) 2014 Elsevier Ltd. All rights reserved.