2-hydroxy-5-methylacetophenone benzoylhydrazone | 114070-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-methylacetophenone benzoylhydrazone
• 英文别名: N-[1-(2-hydroxy-5-methylphenyl)ethylideneamino]benzamide
• CAS: 114070-32-5
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: NUEOBVRTSSKWQA-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-hydroxy-5-methylacetophenone benzoylhydrazone 在 水 、 lead(IV) tetraacetate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.03h， 生成 3-hydroxy-6-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Regioselective quadruple domino aldolization/aldol condensation/Michael/SNAr-cyclization: construction of hexacyclic indeno-fused C-nor-D-homo-steroid frameworks

  摘要：

  An operationally simple and highly atom-economic anionic quadruple domino reaction sequence for the synthesis of hexacyclic indeno-fused naphthalene/quinoline molecules having structural resemblance with the C-nor-D-homo-steroid nucleus has been developed. Promoter and solvent specificity, regioselectivity and mechanistic details were experimentally established. Catalyst concentration and solvent dependent switching of domino steps creating four new C-C bonds are discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.059
• 作为产物：
  描述：

  苯甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-hydroxy-5-methylacetophenone benzoylhydrazone
  参考文献：
  名称：

  Regioselective quadruple domino aldolization/aldol condensation/Michael/SNAr-cyclization: construction of hexacyclic indeno-fused C-nor-D-homo-steroid frameworks

  摘要：

  An operationally simple and highly atom-economic anionic quadruple domino reaction sequence for the synthesis of hexacyclic indeno-fused naphthalene/quinoline molecules having structural resemblance with the C-nor-D-homo-steroid nucleus has been developed. Promoter and solvent specificity, regioselectivity and mechanistic details were experimentally established. Catalyst concentration and solvent dependent switching of domino steps creating four new C-C bonds are discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.059

文献信息

• Synthesis of 1,2-Diacylbenzenes from<i>o</i>-Hydroxyaryl Ketone Acylhydrazones Using [(Diacetoxy)iodo]benzene
  作者：Robert M. Moriarty、Bruce A. Berglund、M. Suresh Chander Rao

  DOI：10.1055/s-1993-25857

  日期：——

  2′-Hydroxyacetophenone and 2′-hydroxypropiophenone acylhydrazones 3 are oxidized to 1,2-diacylbenzenes 4 using [(diacetoxy)-iodo]benzene in dichloromethane at room temperature in a synthetically useful and high yield reaction.

  2′-羟基乙酰苯和2′-羟基丙酰苯肼酮3在室温下使用[(二乙酸氧基)-碘]苯在二氯甲烷中氧化为1,2-二酰基苯4，反应具有合成实用性和高产率。
• Oxidation of N-Aroylhydrazones of o-hydroxyaryl ketones withlead(IV)acetate: A facile route to aromatic o-diketones
  作者：Antigoni Kotali、Petros G. Tsoungas

  DOI：10.1016/s0040-4039(00)96497-9

  日期：1987.1

  N-Aroylhydrazones of o-hydroxyaryl ketones are oxidized with lead(IV)acetate to aromatic o-diketones in a synthetically useful reaction.

  在合成上有用的反应中，用乙酸铅（IV）将邻羟基芳基酮的N-芳酰基hydr氧化为芳族邻二酮。
• Synthesis, structure and solution chemistry of a family of dinuclear hydrazonato-vanadium(V) complexes with [OV(μ-O)VO]4+ core
  作者：Bipul Mondal、Tarun Ghosh、Manas Sutradhar、Gurunath Mukherjee、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.poly.2008.03.018

  日期：2008.6

  [VOL}2μ-O] (1–4) complexes were synthesized from the reaction of [VIVO(acac)2] with an equimolar amount of H2L [H2L is the general abbreviation of hydrazone ligands (H2L1–4) derived from the condensation of benzoyl hydrazine with either 2-hydroxyacetophenone or its para substituted derivatives] in acetone or CH2Cl2 or acetonitrile. These V2O3L2 complexes were also obtained from the reaction of VOSO4 with

  双核trioxidic [VOL} 2 μ-O]（1 - 4）复合物从[V的反应合成IV O（ACAC）2 ]与H的等摩尔量的2 L [ħ 2 L是腙的通用缩写苯甲酰肼与2-羟基苯乙酮或其对位取代衍生物的缩合反应得到的配体（H 2 L 1-4）在丙酮或CH 2 Cl 2或乙腈中。这些V 2 O 3 L 2配合物也是从VOSO 4与H的反应中获得的。在甲醇水溶液（50％V / V）中存在两个当量乙酸钠的情况下，也来自[V IV O（L）（bipy / phen）]络合物在CH 2 Cl 2溶液中的分解，生成2 L乙酸。[V IV O（acac）2 ]分别与H 2 L 2和H 2 L 4反应，得到具有C 2 / c空间群的2和4的黑色单斜晶体。在丙酮中，其中各个配体经完全去质子化的烯醇形式经子午键合到钒上。V–O键的长度遵循以下顺序：V–O（氧代）
• Synthesis, structure and solution chemistry of dioxidovanadium(V) complexes with a family of hydrazone ligands. Evidence of formation of centrosymmetric dimers via H-bonds in the solid state
  作者：Bipul Mondal、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.ica.2010.03.053

  日期：2010.6

  formation of centrosymmetric dimers while the complex 12 (containing only one hydrogen atom in the cationic part) exhibits normal H-bonding. The nature of the H-bonds in each of the four centrosymmetric dimeric complexes is different. These complexes have potential catalytic activity in the aerial oxidation of l -ascorbic acid and are converted into the [VO(L)(hq)] complexes containing VO 3+ motif on reaction

  [V IV O（acac）2]与三齿ONO供体配体（H 2 L 1-4，通用缩写H 2 L；由苯甲酰肼与2-羟基苯乙酮及其5的缩合反应而得）的甲醇溶液反应取代的衍生物）在比吡啶强碱性的中性单齿烷基胺碱（例如乙胺，二乙胺，三乙胺和哌啶）的存在下（一般缩写B）产生BH + [VO 2 L]-（1-16）配合物。这16种络合物中的5种在结构上具有特征，表明钒在扭曲的方形锥体环境中存在于分子的阴离子部分[VO 2 L]-中。配合物5、6、15和16在其阳离子部分包含两个与胺N原子相连的H原子（例如，二乙基铵和哌啶鎓离子）与相邻分子发生H键合，导致形成中心对称的二聚体，而配合物12（在阳离子部分仅含一个氢原子）表现出正常的H键合。四个中心对称二聚体复合物中的每一个的H键性质不同。这些配合物在1-抗坏血酸的空中氧化中具有潜在的催化活性，并在与等摩尔量的8-羟基喹啉（Hhq）在甲醇中反应时转化为含有VO
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: U: SVol.E2, 1.7.5, page 60 - 104
  作者：

  DOI：——

  日期：——