(E)-p-chlorobenzaldehyde N,N-dimethylhydrazone | 138616-25-8

• 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)-p-chlorobenzaldehyde N,N-dimethylhydrazone
• 英文别名: p-Chlorobenzaldehyde dimethylhydrazone；N-[(E)-(4-chlorophenyl)methylideneamino]-N-methylmethanamine
• CAS: 138616-25-8
• 化学式: C₉H₁₁ClN₂
• 分子量: 182.653
• InChiKey: JWRGEPOIPOSDQN-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (E)-p-chlorobenzaldehyde N,N-dimethylhydrazone 在 吡啶 、 盐酸 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 1-(4-chlorophenyl)-3,3,3-trifluoropropan-1-one
  参考文献：
  名称：

  Convenient Synthesis of 1,1,1-Trifluoro-4,5-diaza-2,4-alkadienes and 1-Aryl-3,3,3- trifluoro-1-propanones

  摘要：

  通过与过量的三氟乙酸酐在吡啶中反应，由芳烃甲醛二甲基腙1或其三氟乙酰化衍生物2以良好的产率合成了几种3-芳基-1,1,1-三氟-4,5-二氮杂-2,4-链二烯3。 3的酸水解以高产率得到1-芳基-3,3,3-三氟-1-丙酮4。

  DOI：

  10.1055/s-1989-27144
• 作为产物：
  描述：

  偏二甲肼 、 4-氯苯甲醛 生成 (E)-p-chlorobenzaldehyde N,N-dimethylhydrazone
  参考文献：
  名称：

  （E）-到（Z）-N，N-二甲基hydr的光异构化和热还原

  摘要：

  脂肪醛N，N-二甲基hydr的E-异构体在UV（254 nm）辐射下经历竞争性E - Z异构化和光解成腈。所述ž - ë异构体混合物，这导致热恢复到更稳定的È异构体和下短的辐照时间的光异构化/热循环逆转可以是可逆的。三甲基乙醛N，N-二甲基hydr经历相似的反应（排除其他类型的异构化的干预），RCH的热Z → E反应速率N–NMe 2的顺序为R = Bu t > Et> Me。根据the的构象和E - Z异构化的机理来考虑结果。

  DOI：

  10.1039/p29910001649

文献信息

• Palladium-Catalyzed C(sp² )−H Alkylation of Aldehyde-Derived Hydrazones with Functionalized Difluoromethyl Bromides
  作者：Alexis Prieto、Romain Melot、Didier Bouyssi、Nuno Monteiro

  DOI：10.1002/anie.201510334

  日期：2016.1.26

  A palladium‐catalyzed C(sp2)−H difluoromethylation of aldehyde‐derived hydrazones using bromodifluoromethylated compounds to afford the corresponding functionalized difluoromethylketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a difluoroalkyl radical may be involved in the catalytic cycle. Applications of the methodology to the synthesis of α,α‐difluoro‐β‐ketoesters

  已建立了使用溴二氟甲基化化合物的钯催化的醛基的C（sp 2）-H二氟甲基化反应，以提供相应的官能化二氟甲基酮。提出经由二氟烷基自由基进行的自由基/ SET机理可能参与催化循环。说明了该方法在合成α，α-二氟-β-酮酸酯和α，α-二氟酮（RCOCF 2 H）中的应用。
• Weber, Lutz; Muehlstaedt, Manfred, Zeitschrift fur Chemie, 1988, vol. 28, # 1, p. 26 - 27
  作者：Weber, Lutz、Muehlstaedt, Manfred

  DOI：——

  日期：——
• Elimination reactions of hydrazonium salts: experimental and theoretical evidence for a large stereoelectronic effect of nitrogen
  作者：Nguyen Minh Tho、Leo F. Clarke、Anthony F. Hegarty

  DOI：10.1021/jo00312a026

  日期：1990.12
• Direct synthesis of dithioketals from N,N-dialkylhydrazones
  作者：Elena Díez、Ana M López、Carmen Pareja、Eloísa Martín、Rosario Fernández、JoséM Lassaletta

  DOI：10.1016/s0040-4039(98)01728-6

  日期：1998.10

  Direct dithioketalisation of N,N-dialkylhydrazones promoted by BF3. Et2O or p-TsOH and 1,2-ethanedithiol in dry medium affords the corresponding dithiolanes in nearly quantitative yields. A variety of hydrazones derived from several kinds of aldehydes (aliphatic, aromatic, and alpha,beta-unsaturated) and hydrazines [N, N-dimethylhydrazine, 1-aminopyrrolidine, and (S)-1-amino-2- (methoxymethyl)pyrrolidine (SAMP)] were reacted, indicating the generality of the method. The reaction was demonstrated to proceed without racemization of a particularly sensitive chiral substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Syntheses and structures of exo- and endo-cyclopalladated phenylhydrazones
  作者：Jaume Granell、Rosa Moragas、Joaquim Sales、Mercè Font-Bardía、Xavier Solans

  DOI：10.1039/dt9930001237

  日期：——

  The reaction of substituted benzylidenephenylhydrazones with palladium(II) salts has been found to give exo in preference to endo five-membered metallacycles. The endo derivatives can only be obtained if the hydrazone phenyl ring contains chlorine substituents in the ortho or meta positions. The tendency of these hydrazone ligands to give exo derivatives, in contrast to the results found with similar N-benzylideneamines which favour the formation of endo-palladocycles, can be explained by the planarity of the hydrazone ligands, which favours the interaction of the C-H bond of the hydrazone phenyl ring with the palladium. Moreover, the aminic nitrogen atom activates this phenyl ring to electrophilic attack. The crystal structures of two of the metallacycles have been determined.

表征谱图