bis(N,N'-diphenylhydrazone) of glyoxal | 83799-85-3

• 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: bis(N,N'-diphenylhydrazone) of glyoxal
• 英文别名: glyoxal-bis-diphenylhydrazone；Glyoxal-bis-diphenylhydrazon；Glyoxal-diphenylosazon；Glyoxal-bis-(1,1-diphenylhydrazon)；N-[2-(diphenylhydrazinylidene)ethylideneamino]-N-phenylaniline
• CAS: 83799-85-3
• 化学式: C₂₆H₂₂N₄
• 分子量: 390.487
• InChiKey: HDSSPAGQOWQIST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  palladium dichloride 、 bis(N,N'-diphenylhydrazone) of glyoxal 以 neat (no solvent) 为溶剂， 以95%的产率得到1-diphenylamino-10-chloro-5-phenyl-1,3,2-diazapalladolo[1,2-b]-1,2,3-benzodiazapalladol
  参考文献：
  名称：

  Cyclopalladated Complexes Derived from Diphenylhydrazones and their Transmetallation Reaction

  摘要：

  Mononuclear cyclopalladated complexes of type PdCl(Ph2N-N=CR1-C-R-2=N-NPh2), where R-1=R-2=H (2a), R-1= R-2=CH3 (2b), and R-1=H, R-2=CH3 (2c) were synthesized by the reaction of palladium chloride and hydrazones. Additionally, the reaction of the complex 2c towards lithium phenylacetylide was studied, giving Ph2N-N = C(CH3)-CH = N-N(Ph)(o-C6H4- -C-C-Ph) (3). The complexes 2a-2c and compound 3 were characterized by IR, Mass, H-1, C-13, and 2D NMR spectroscopy. X-ray structure of complex 2c was also determined.

  DOI：

  10.1002/1521-3749(200209)628:9/10<2104::aid-zaac2104>3.0.co;2-a
• 作为产物：
  描述：

  草酸醛 、 1,1-二苯肼盐酸盐 以 甲醇 、 水 为溶剂， 反应 16.0h， 以67%的产率得到bis(N,N'-diphenylhydrazone) of glyoxal
  参考文献：
  名称：

  Palladium-catalyzed decarboxylative coupling of benzoic acid derivatives using hydrazone ligands

  摘要：

  Palladium-catalyzed decarboxylative coupling of benzoic acid derivatives with arylboroxins gave biaryls using a catalytic amount of Pd(TFA)(2)-hydrazone Id system with Ag2CO3 at 80 degrees C in good yields. We also found that decarboxylative coupling with aryl(trialkoxy)silanes gave biaryls using a Pd(TFA)(2)-hydrazone 1g system with AgF in good yields. 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.017

文献信息

• Wohl; Neuberg, Chemische Berichte, 1900, vol. 33, p. 3108
  作者：Wohl、Neuberg

  DOI：——

  日期：——
• Palladium-catalyzed decarboxylative coupling of benzoic acid derivatives using hydrazone ligands
  作者：Takashi Mino、Eri Yoshizawa、Kohei Watanabe、Taichi Abe、Kiminori Hirai、Masami Sakamoto

  DOI：10.1016/j.tetlet.2014.04.017

  日期：2014.5

  Palladium-catalyzed decarboxylative coupling of benzoic acid derivatives with arylboroxins gave biaryls using a catalytic amount of Pd(TFA)(2)-hydrazone Id system with Ag2CO3 at 80 degrees C in good yields. We also found that decarboxylative coupling with aryl(trialkoxy)silanes gave biaryls using a Pd(TFA)(2)-hydrazone 1g system with AgF in good yields. 2014 Elsevier Ltd. All rights reserved.
• Cyclopalladated Complexes Derived from Diphenylhydrazones and their Transmetallation Reaction
  作者：Fernando Ortega-Jiménez、Elizabeth Gómez、Pankaj Sharma、M. Carmen Ortega-Alfaro、Rubén A. Toscano、Cecilio Alvarez-Toledano

  DOI：10.1002/1521-3749(200209)628:9/10<2104::aid-zaac2104>3.0.co;2-a

  日期：2002.9

  Mononuclear cyclopalladated complexes of type PdCl(Ph2N-N=CR1-C-R-2=N-NPh2), where R-1=R-2=H (2a), R-1= R-2=CH3 (2b), and R-1=H, R-2=CH3 (2c) were synthesized by the reaction of palladium chloride and hydrazones. Additionally, the reaction of the complex 2c towards lithium phenylacetylide was studied, giving Ph2N-N = C(CH3)-CH = N-N(Ph)(o-C6H4- -C-C-Ph) (3). The complexes 2a-2c and compound 3 were characterized by IR, Mass, H-1, C-13, and 2D NMR spectroscopy. X-ray structure of complex 2c was also determined.