hydrocinnamaldehyde N,N-dimethylhydrazone | 139546-57-9

• 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: hydrocinnamaldehyde N,N-dimethylhydrazone
• 英文别名: dihydrocinnamaldehyde dimethylhydrazone；N-methyl-N-(3-phenylpropylideneamino)methanamine
• CAS: 139546-57-9
• 化学式: C₁₁H₁₆N₂
• 分子量: 176.261
• InChiKey: GDDUTUNPOYLHEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  272.4±33.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hydrocinnamaldehyde N,N-dimethylhydrazone 在 磷酸吡哆醛 、 chromobacterium violaceum transaminase 、 异丙胺 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 3-苯基-1-丙胺
  参考文献：
  名称：

  使用转氨酶将腙直接转化为胺

  摘要：

  醛和酮与转氨酶的反应已广泛用于生产胺。在这里，探索了腙和转氨酶之间的新转化。研究了几种底物，以良好的收率形成了多种胺。发现通过添加亲电试剂可以提高胺产率，这被认为可以“捕获”反应中释放的肼。

  DOI：

  10.1002/cctc.202101008
• 作为产物：
  描述：

  苯丙醛 、 偏二甲肼 反应 0.5h， 以10.0 g的产率得到hydrocinnamaldehyde N,N-dimethylhydrazone
  参考文献：
  名称：

  The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction

  摘要：

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.121

文献信息

• Synthesis of multi-substituted 1,2,4-triazoles utilising the ambiphilic reactivity of hydrazones
  作者：Haruo Matsuzaki、Norihiko Takeda、Motohiro Yasui、Mayuko Okazaki、Seishin Suzuki、Masafumi Ueda

  DOI：10.1039/d1cc05326d

  日期：——

  The synthesis of N-alkyl-1H-1,2,4-triazoles from N,N-dialkylhydrazones and nitriles via formal [3+2] cycloaddition including the C-chlorination/nucleophilic addition/cyclisation/dealkylation sequence was developed. This sequential reaction utilising the in situ generation of hydrazonoyl chloride based on the ambiphilic reactivity of hydrazones afforded a variety of multi-substituted N-alkyl-triazoles

  合成ñ -烷基-1 ħ从-1,2,4-三唑Ñ，Ñ -dialkylhydrazones和腈经由正式[3 + 2]环加成，包括Ç -chlorination /亲核加成/环化/脱烷基化序列被开发。这种基于腙的双亲反应性原位生成腙酰氯的连续反应以高产率提供了多种多取代的N-烷基-三唑。多取代三唑的合成效用也通过进一步的转化得到了证明。
• Copper-Catalyzed C(sp²)–H Difluoroalkylation of Aldehyde Derived Hydrazones with Diboron as Reductant
  作者：Miaolin Ke、Qiuling Song

  DOI：10.1021/acs.joc.6b00324

  日期：2016.5.6

  An efficient and general method for C(sp2)–H difluoroalkylation of aldehyde derived hydrazones via a CuII/B2pin2-catalyzed reaction between difluoroalkyl bromides and hydrazones was developed. In this reaction, both aromatic and aliphatic difluoroalkylated aldehyde derived hydrazones could be achieved in good to excellent yields. For some heteroaromatic aldehyde derived hydrazones, two fluoroacetates

  通过Cu II / B 2 pin 2催化的二氟烷基溴与的反应，开发了一种有效且通用的醛衍生的C（sp 2）-H二氟烷基化方法。在该反应中，芳族和脂族二氟烷基化醛衍生的azo均可以良好至优异的产率获得。对于某些杂芳族醛衍生的azo，可以将两种氟乙酸酯引入最终产物中。初步的机理研究表明，通过SET途径的二氟烷基自由基参与了反应。另外，催化二硼试剂在该转化中起着不可或缺的作用。
• One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation
  作者：Nataliya A. Markina、Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1039/c2ob07117g

  日期：——

  The reaction of readily accessible 1,1-dialkylhydrazones with commercially available o-(trimethylsilyl)aryl triflates provides a direct one-step route to pharmaceutically important 1-alkylindazoles. The products are obtained in high yields by one-pot NCS-chlorination/aryne annulation or Ac2O-acylation/deprotection/aromatization protocols.

  容易获得的1,1-二烷基肼酮与市售的o-(三甲基硅基)芳基三氟甲磺酸酯反应，提供了一种直接的一步法合成药物重要的1-烷基吡唑并的途径。通过一次性NCS氯化/芳烃环化或Ac2O酰化/去保护/芳香化方案，可以高产率地获得产物。
• Giurg; Mlochowski; Ambrozak, Polish Journal of Chemistry, 2002, vol. 76, # 12, p. 1713 - 1720
  作者：Giurg、Mlochowski、Ambrozak

  DOI：——

  日期：——
• The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction
  作者：Nathan T. Reynolds、Tomislav Rovis

  DOI：10.1016/j.tet.2005.03.121

  日期：2005.6

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.