(2'-hydroxy-5'-chloroacetophenone)benzoylhydrazone | 736940-22-0

• 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: (2'-hydroxy-5'-chloroacetophenone)benzoylhydrazone
• 英文别名: 5-chloro-2-hydroxyacetophenone benzoylhydrazone；5-chloro-2-hydroxyacetophenone benzoyl hydrazone；N-[1-(5-chloro-2-hydroxyphenyl)ethylideneamino]benzamide
• CAS: 736940-22-0
• 化学式: C₁₅H₁₃ClN₂O₂
• 分子量: 288.733
• InChiKey: ZQAYLTHKLYBTAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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'-chloroacetophenone)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 4.0h， 生成 2,11-dichloro-13b-phenylbenzo[a]indeno[1,2-c]fluorene-9,14(8bH,13bH)-dione
  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'-chloroacetophenone)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, 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
• SUBSTITUTED (E)-N'-(1-PHENYLETHYLIDENE)BENZOHYDRAZIDE ANALOGS AS HISTONE DEMETHYLASE INHIBITORS
  申请人：Vankayalapati Hariprasad

  公开号：US20140163017A1

  公开（公告）日：2014-06-12

  In one aspect, the invention relates to substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs, derivatives thereof, and related compounds, which are useful as inhibitors of lysine-specific histone demethylase, including LSD1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the LSD1. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，本发明涉及取代的(E)-N′-(1-苯乙烯基)苯肼类似物、其衍生物和相关化合物，它们可用作赖氨酸特异性组蛋白去甲基化酶，包括LSD1的抑制剂；制备这些化合物的合成方法；含有这些化合物的制药组合物；以及使用这些化合物和组合物治疗与LSD1功能障碍相关的疾病的方法。本摘要旨在作为搜索特定技术领域的扫描工具，不旨在限制本发明。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: U: SVol.E2, 1.7.5, page 60 - 104
  作者：

  DOI：——

  日期：——
• Synthesis, structure and solution chemistry of quaternary oxovanadium(V) complexes incorporating hydrazone ligands
  作者：Bipul Mondal、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.ica.2009.02.043

  日期：2009.7

  [VIVO(acac)(2)] reacts with an equimolar amount of benzoyl hydrazone of 2-hydroxyacetophenone (H2L1) or 5-chloro-2-hydroxyacetophenone (H2L2) in the presence of excess pyridine (py) in methanol to produce the quaternary [(VO)-O-V(L-1)(OCH3)(py)] (1) and [(VO)-O-V(L-2)(OCH3)(py)] (2) complexes, respectively, while under similar condition, the benzoyl hydrazones of 2-hydroxy-5-methylacetophenone (H2L3) and 2-hydroxy-5-methoxyacetophenone (H2L4) afforded only the methoxy bridged dimeric [(VO)-O-V(L-3/L-4)(OCH3)](2) complexes. The X-ray structural analysis of 1 and 2 indicates that the geometry around the metal is distorted octahedral where the three equatorial positions are occupied by the phenolate-O, enolate-O and the imine-N of the fully deprotonated hydrazone ligand in its enolic form and the fourth one by a methoxide-O atom. An oxo-O and a pyridine-N atom occupy two axial positions. Quaternary complexes exhibit one quasi-reversible one-electron reduction peak near 0.25 V versus SCE in CH2Cl2 and they decompose appreciably to the corresponding methoxy bridged dimeric complex in CDCl3 solution as indicated by their H-1 NMR spectra. These quaternary VO3+ complexes are converted to the corresponding V2O34+-complexes simply on refluxing them in acetone and to the VO2+-complexes on reaction with KOH in methanol. An equimolar amount of 8-hydroxyquinoline (Hhq) converts these quaternary complexes to the ternary [(VO)-O-V(L)(hq)] complexes in CHCl3. (C) 2009 Elsevier B. V. All rights reserved.