p-methoxybenzaldehyde 4-phenylsemicarbazone | 91991-04-7

• 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: p-methoxybenzaldehyde 4-phenylsemicarbazone
• 英文别名: 4-methoxy-benzaldehyde-(4-phenyl semicarbazone)；4-Methoxy-benzaldehyd-(4-phenyl-semicarbazon)；4-Phenyl-1-anisal-semicarbazid；Anisaldehyd-phenylsemicarbazon；1-[(4-Methoxyphenyl)methylideneamino]-3-phenylurea
• CAS: 91991-04-7
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: XRWZKLFYEYRJAG-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-methoxybenzaldehyde 4-phenylsemicarbazone 在 dimethylammonium chlorochromate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 4-甲氧基苯甲醛
  参考文献：
  名称：

  用于从肟、缩氨基脲、4-苯基缩氨基脲和对硝基苯腙中再生羰基化合物的高效、选择性和廉价的负载型氧化剂

  摘要：

  摘要 吸附在硅胶上的氯铬酸二甲基铵 (DMCC/SiO2) 可以在温和和非水条件下以良好的收率从肟、缩氨基脲、4-苯基缩氨基脲和对硝基苯腙中再生羰基化合物。

  DOI：

  10.1080/00397910008087230
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 4-苯基氨基脲 生成 p-methoxybenzaldehyde 4-phenylsemicarbazone
  参考文献：
  名称：

  Borsche; Gerhardt, Chemische Berichte, 1914, vol. 47, p. 2910

  摘要：

  DOI：

文献信息

• An Efficient, Selective and Inexpensive Supported Oxidant for the Regeneration of Carbonyl Compounds from Oximes, Semicarbazones, 4-Phenylsemicarbazones, and P-Nitrophenylhydrazones
  作者：Gui-Sheng Zhang、Bing Chai

  DOI：10.1080/00397910008087230

  日期：2000.4

  Abstract Dimethylammonium chlorochromate adsorbed on silica gel (DMCC/SiO2) makes the regeneration of carbonyl compounds from oximes, semicarbazones, 4-phenyl-semicarbazones, and p-nitrophenylhydrazones in good yields under mild and non-aqueous conditions.

  摘要 吸附在硅胶上的氯铬酸二甲基铵 (DMCC/SiO2) 可以在温和和非水条件下以良好的收率从肟、缩氨基脲、4-苯基缩氨基脲和对硝基苯腙中再生羰基化合物。
• Synthesis of pyrazolines by a site isolated resin-bound reagents methodology
  作者：Vincent Gembus、Jean-Jacques Bonnet、François Janin、Pierre Bohn、Vincent Levacher、Jean-François Brière

  DOI：10.1039/c004704j

  日期：——

  achieved by an organocatalysed aza-Michael/transimination domino sequence between hydrazones and enones making use of a mixture of heterogeneous resin-bound acid/base reagents. This methodology nicely illustrates the site isolation concept of supported reagents allowing the simultaneous use of otherwise destructive reactive functionalities.

  生物学上重要的3,4-取代的吡唑啉的制备是通过使用异质树脂结合的酸/碱试剂的混合物在和烯酮之间进行有机催化的aza-Michael /氨基化多米诺序列实现的。该方法很好地说明了支持试剂的位点隔离概念，允许同时使用其他破坏性反应功能。
• Ramachander; Srinivasan, Current Science, 1959, vol. 28, p. 368
  作者：Ramachander、Srinivasan

  DOI：——

  日期：——
• Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands
  作者：Vincent Gembus、Christophe Furman、Régis Millet、Roxane Mansouri、Philippe Chavatte、Vincent Levacher、Jean-François Brière

  DOI：10.1016/j.ejmech.2012.10.031

  日期：2012.12

  In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [S-35]-GTP gamma S binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure activity relationship. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Borsche; Gerhardt, Chemische Berichte, 1914, vol. 47, p. 2910
  作者：Borsche、Gerhardt

  DOI：——

  日期：——