4-chloro-salicylaldehyde acetylhydrazone | 19161-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-chloro-salicylaldehyde acetylhydrazone
• 英文别名: N-(acetyl)-N'-(5-Cl-salicylidene)hydrazine；H2ahsCl；N-Acetyl-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin；N-[(5-chloro-2-hydroxyphenyl)methylideneamino]acetamide
• CAS: 19161-56-9
• 化学式: C₉H₉ClN₂O₂
• 分子量: 212.636
• InChiKey: MKKMIMNDJUCTTI-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-salicylaldehyde acetylhydrazone 在 lead(IV) tetraacetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-acetyl-5-chloro-benzaldehyde
  参考文献：
  名称：

  通过 H3PMo12O40 催化 2-酰基苯甲酸与苯甲醇环化反应区域选择性和立体选择性合成 (Z)-3-Ylidenephthalides

  摘要：

  我们报告了在 2-酰基苯甲酸与醇的酯化和环化反应以区域选择性和立体选择性合成 ( Z )-3-亚芳基苯酞之后形成的完全串联的 C-O 和 C-C 键。该反应使用无毒、廉价的 H 3 PMo 12 O 40作为催化剂，并产生水作为唯一的副产物，使该反应对环境无害且可持续。此外，该反应具有环境友好的反应条件，易于扩展，产品易于衍生为药物和生物活性化合物。机理研究和密度泛函理论计算表明，合适的酸催化剂是这种转化选择性的关键。

  DOI：

  10.1002/cjoc.202100397
• 作为产物：
  描述：

  乙酰肼 、 5-氯代水杨醛 以 乙醇 为溶剂， 反应 12.0h， 生成 4-chloro-salicylaldehyde acetylhydrazone
  参考文献：
  名称：

  通过 H3PMo12O40 催化 2-酰基苯甲酸与苯甲醇环化反应区域选择性和立体选择性合成 (Z)-3-Ylidenephthalides

  摘要：

  我们报告了在 2-酰基苯甲酸与醇的酯化和环化反应以区域选择性和立体选择性合成 ( Z )-3-亚芳基苯酞之后形成的完全串联的 C-O 和 C-C 键。该反应使用无毒、廉价的 H 3 PMo 12 O 40作为催化剂，并产生水作为唯一的副产物，使该反应对环境无害且可持续。此外，该反应具有环境友好的反应条件，易于扩展，产品易于衍生为药物和生物活性化合物。机理研究和密度泛函理论计算表明，合适的酸催化剂是这种转化选择性的关键。

  DOI：

  10.1002/cjoc.202100397

文献信息

• Synthesis of 3,3′‐Disubstituted Isobenzofuran‐1(3 <i>H</i> )‐Ones via Cs _0.5 H _2.5 PW ₁₂ O ₄₀ ‐Catalyzed Difunctionalization of Carbonyls
  作者：Yu‐Feng Liu、Gang‐Ming Cao、Lei Chen、Ke Li、Xiao‐Ling Lin、Xin‐Xin Xu、Zhang‐Gao Le、Guo‐Ping Yang

  DOI：10.1002/adsc.202200081

  日期：2022.4.12

  We reported a method for the synthesis of 3,3′-disubstituted isobenzofuran-1(3H)-ones via the carbonyl difunctionalization of 2-acylbenzoic acids. A range of nucleophiles was reacted with 2-acylbenzoic acids to furnish the functionalized isobenzofuran-1(3H)-ones with the factual yield range of 61–96%. The reaction uses Cs0.5H2.5PW12O40 as a catalyst and produces water as the sole by-product. Various

  我们报道了一种通过2-酰基苯甲酸的羰基双官能化合成 3,3'-二取代异苯并呋喃-1(3 H )-酮的方法。一系列亲核试剂与 2-酰基苯甲酸反应以提供功能化的异苯并呋喃-1(3 H )-酮，实际产率范围为 61-96%。该反应使用 Cs 0.5 H 2.5 PW 12 O 40作为催化剂并产生水作为唯一的副产物。各种官能团可以通过以下方式引入到 isobenzofuran-1(3 H ) -one 骨架C-P/C-N/C-O/C-C 键的形成，这将为合成潜在的生物活性分子提供机会。在初步实验的基础上，提出了一种合理的机制。
• Ruthenium(III) complexes with N-(acetyl)-N′-(5-R-salicylidene)hydrazines: Syntheses, structures and properties
  作者：Raji Raveendran、Samudranil Pal

  DOI：10.1016/j.poly.2007.10.027

  日期：2008.2

  The reactions of 1 mol equiv. each of [Ru(PPh3)(3)Cl-2] and N-(acetyl)-N'-(5-R-salicylidene)hydrazines (H(2)ahsR, R = H, OCH3, Cl, Br and NO2) in alcoholic media afford simultaneously two types of complexes having the general formulae [Ru(HahsR)(PPh3)(2)Cl-2] and [Ru(ahsR)(PPh3)(2)Cl]. The complexes have been characterized by elemental analysis, magnetic, spectroscopic and electrochemical measurements. Molecular structures of [Ru(HahsH)(PPh3)(2)Cl-2] and [Ru(ahsH)(PPh3)(2)Cl] have been confirmed by X-ray crystallography. In both species, the PPh3 ligands are trans to each other. The bidentate HahsH(-) coordinates to the metal ion via the 0 atom of the deprotonated amide and the imine-N atom in [Ru(HahsH)(PPh3)(2)Cl-2]. In HahsH(-), the phenolic OH is involved in a strong intramolecular hydrogen bond with the uncoordinated amide N atom forming a seven-membered ring. In [Ru(ahsH)(PPh3)(2)Cl], the tridentate ahsH(2-) binds to the metal ion via the deprotonated amide 0, the imine N and the phenolate 0 atoms. In the electronic spectra, the green [Ru(HahsR)(PPh3)(2)Cl-2] and brown [Ru(ahsR)(PPh3)(2)Cl] complexes display several absorptions in the ranges 385-283 and 457-269 nm, respectively. Both complexes are low-spin and display rhombic EPR spectra in frozen solutions. Both types of complexes are redox active and display a quasi-reversible ruthenium(III) to ruthenium(II) reduction which is sensitive to the polar effect of the substituent on the chelating ligand. The reduction potentials are in the ranges -0.21 to -0.12 and -0.42 to -0.21 V (versus Ag/AgCl) for [Ru(HahsR)(PPh3)(2)Cl-2] and [Ru(ahsR)(PPh3)(2)Cl], respectively. (c) 2007 Elsevier Ltd. All rights reserved.
• Levchenkov; Lukov; Shcherbakov, Russian Journal of Coordination Chemistry, 1998, vol. 24, # 5, p. 332 - 336
  作者：Levchenkov、Lukov、Shcherbakov、Kogan

  DOI：——

  日期：——
• Lukov; Levchenkov; Kogan, Russian Journal of Inorganic Chemistry, 1997, vol. 42, # 4, p. 532 - 535
  作者：Lukov、Levchenkov、Kogan

  DOI：——

  日期：——
• Protolitic complexing properties of acylhydrazones of substituted salicylaldehydes and stability constants of their cooper(II) complexes
  作者：L. D. Popov、O. I. Askalepova、S. I. Levchenkov、V. A. Kogan

  DOI：10.1134/s0036023607040274

  日期：2007.4

  The acid-base properties of acetyl-and heptoylhydrazones of substituted salicylaldehyde derivatives and the stability of their copper(II) complexes have been studied. For both sets of compounds, the ionization constants of the hydrazones and the stability constants of hydrazone complexes are linear functions of the substituent constants sigma. An analogous tendency is found for the antiferromagnetic exchange interaction parameters in dimeric copper(II) nitrate complexes of heptoylhydrazones of substituted salicylaldehyde derivatives. A correlation between the protolytic properties of hydrazones and the magnetic properties of their complexes is suggested.