4-bromo-salicylaldehyde acetylhydrazone | 143361-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-salicylaldehyde acetylhydrazone
• 英文别名: N-(acetyl)-N'-(5-Br-salicylidene)hydrazine；H2ahsBr；N-[(5-bromo-2-hydroxyphenyl)methylideneamino]acetamide
• CAS: 143361-71-1
• 化学式: C₉H₉BrN₂O₂
• 分子量: 257.087
• InChiKey: YTJMMCWCOHWNLC-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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-bromo-salicylaldehyde acetylhydrazone 在 lead(IV) tetraacetate 作用下， 以 四氢呋喃 为溶剂， 生成 2-acetyl-5-bromobenzaldehyde
  参考文献：
  名称：

  H4SiW12O40催化三组分串联反应合成3,3-二取代异吲哚啉酮

  摘要：

  开发了AH 4 SiW 12 O 40催化的2-酰基苯甲酸、伯胺和氧化膦的三组分串联反应以形成3,3-二取代异吲哚啉酮。通过使用 H 4 SiW 12 O 40作为催化剂和碳酸二甲酯 (DMC) 作为溶剂，各种 2-酰基苯甲酸衍生物和伯胺都能很好地产生 C3-膦酰基官能化的 3,3-二取代异吲哚啉酮收率范围为61%-87%。这种转化的优点包括绿色催化剂和溶剂、可用的起始原料、广泛的底物范围、高效率和操作简单，水作为唯一的副产物。该策略实现了高效、绿色的分子片段组装来获取异吲哚啉酮，这将为以绿色方式合成潜在的生物活性分子提供机会。

  DOI：

  10.1016/j.cclet.2023.108480
• 作为产物：
  描述：

  乙酰肼 、 5-溴水杨醛 以 乙醇 为溶剂， 反应 12.0h， 生成 4-bromo-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。
• Regio‐ and Stereoselective Synthesis of ( <i>Z</i> )‐ <scp>3‐Ylidenephthalides</scp> <i>via</i> <scp> H ₃ PMo ₁₂ O ₄₀ ‐Catalyzed </scp> Cyclization of <scp>2‐Acylbenzoic</scp> Acids with Benzylic Alcohols
  作者：Guoping Yang、Ke Li、Xiaoling Lin、Yijin Li、Chengxing Cui、Shixiong Li、Yuanyuan Cheng、Yufeng Liu

  DOI：10.1002/cjoc.202100397

  日期：2021.11

  We report an exclusively tandem C—O and C—C bond forming beyond the esterification and cyclization reaction of 2-acylbenzoic acids with alcohols to regio- and stereoselective synthesis of the (Z)-3-ylidenephthalides. The reaction uses the nontoxic, inexpensive H3PMo12O40 as catalyst and produces water as the sole by-product, making the reaction environmentally benign and sustainable. Moreover, this

  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。
• Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes
  作者：Tanmoy Chanda、Sushobhan Chowdhury、Namrata Anand、Suvajit Koley、Ashutosh Gupta、Maya Shankar Singh

  DOI：10.1016/j.tetlet.2015.01.077

  日期：2015.2

  First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spiro-cyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol. (C) 2015 Elsevier Ltd. All rights reserved.
• 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：——