O-(4-chlorobenzoyl)-salicylic acid | 88875-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: O-(4-chlorobenzoyl)-salicylic acid
• 英文别名: 2-(4-Chlorobenzoyl)oxybenzoic acid
• CAS: 88875-74-5
• 化学式: C₁₄H₉ClO₄
• 分子量: 276.676
• InChiKey: HNDKZCVGVFSTSK-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C(Solv: benzene (71-43-2))
• 沸点：
  508.1±35.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-(4-chlorobenzoyl)-salicylic acid 在 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 4'-氯黄酮
  参考文献：
  名称：

  通过分子内wittig反应的新型4H-chromen-4-ones合成

  摘要：

  由O-酰基（芳酰基）水杨酸的甲硅烷基酯与（三甲基甲硅烷基）亚甲基三苯基膦烷的甲硅烷基酯的反应顺序形成的酰基磷光烷在酯羰基上进行分子内的Wittig环化反应，得到良好或优异的4H-铬4--4-产量。

  DOI：

  10.1021/ol006518p
• 作为产物：
  描述：

  3-Hydroxy-4'-chloroflavone 在 C₃₀H₂₃FeN₂O₆ 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 O-(4-chlorobenzoyl)-salicylic acid
  参考文献：
  名称：

  非血红素铁催化剂对黄酮醇和3-羟基-4（1 H）-喹诺酮2,4-二加氧酶的作用进行仿生的血红素铁催化剂的生物启发性黄酮醇和喹诺酮双加氧反应

  摘要：

  单核络合物Fe III（O -bs）（salen）（salenH 2  = 1,6-双（2-羟基苯基）-2,5-二氮杂-六-1,5-二烯; O -bsH = O-苯甲酰水杨酸 酸）合成为合成的酶-深度复合物，并通过光谱法和X射线晶体分析进行了表征。在催化量的Fe III（O -bs）（salen）存在下，黄酮醇（flaH）和3-羟基-4-喹诺酮（quinH 2）衍生物的双氧化作用导致杂环的氧化裂解，得到相应的Ø-苯甲酰基水杨酸和邻氨基苯甲酸衍生物，同时释放一氧化碳。这些反应可以被认为是仿生功能模型，与含铁的黄酮醇和不依赖辅因子的3-羟基-4（1 H）-喹诺酮2,4-二加氧酶有关。

  DOI：

  10.1016/j.jinorgbio.2011.11.013

文献信息

• Studies on benzhydryl derivatives. IV. Synthesis and anti-inflammatory activity of 2-O-(diphenylacetyl)salicylic acids.
  作者：SHOJI TAKEMURA、YOSHIKO AZUMA、CHIYUKI SHOGAKI、YASUYOSHI MIKI、HIKARU NAGATOMI、BOMPEI YASUI、KAZUKO ANDO

  DOI：10.1248/cpb.31.2632

  日期：——

  A synthetic route to 2-O-(diphenylacetyl)salicylic acid derivatives was developed and the effects of the products on the heat-denaturation of albumin and on heat-induced erythrocytolysis were examined (in vitro anti-inflammation test). Trichloroethyl salicylate was acylated with diphenylacetic acid and its derivatives in the presence of methanesulfonyl chloride and pyridine, and the products were deprotected with zinc-acetic acid to give 2-O-(diphenylacetyl)salicylic acid derivatives. Their biological effects resembled those of ibuprofen.

  开发了一条合成2-O-(二苯乙酰基)水杨酸衍生物的路线，并考察了产品对白蛋白热变性及热致红细胞溶血的影响（体外抗炎试验）。水杨酸三氯乙酯在甲磺酰氯和吡啶存在下与二苯乙酸及其衍生物进行酰化反应，产物用乙酸锌脱保护得到2-O-(二苯乙酰基)水杨酸衍生物。它们的生物效应与布洛芬相似。
• Kinetics and Mechanism of the Oxygenation of Potassium Flavonolate. Evidence for an Electron Transfer Mechanism
  作者：László Barhács、József Kaizer、Gábor Speier

  DOI：10.1021/jo991926w

  日期：2000.6.1

  0.10) x 10(-1), DeltaH()/kJ mol(-1) = 29 +/- 2, DeltaS/J mol(-1) K(-1) = -161 +/- 6. The reaction fits a Hammett linear free energy relationship for 4'-substituted flavonols, and electron-releasing groups make the oxygenation reaction faster. The anodic oxidation wave potentials E(a) of the 4'-substituted flavonolates correlate well with reaction rates. At more negative E(a) values faster reaction

  在绝对DMF中黄酮醇（flaH）的钾盐的氧合导致O-苯甲酰水杨酸钾和一氧化碳在40°C时产率为95％。动力学测量得出速率定律-d [flaK] / dt = k（2 ）[flaK] [O（2）]。速率常数，激活焓和313.16 K处的熵如下：k（2）/ M（-）（1）s（-1）=（3.28 +/- 0.10）x 10（-1），DeltaH（ ）/ kJ mol（-1）= 29 +/- 2，DeltaS / J mol（-1）K（-1）= -161 +/-6。该反应符合4'-取代的Hammett线性自由能关系黄酮醇和释放电子的基团使氧化反应更快。4'-取代的黄酮酸酯的阳极氧化波电势E（a）与反应速率密切相关。在更多的负E（a）值观察到更快的反应速率。反应混合物的EPR光谱（g = 2.0038，dH = 1.8 G，a（H）= 0。
• New simple wittig-type cyclizations to flavones, 4-quinolones and indenones
  作者：Helmut Vorbrüggen、Bernhard D. Bohn、Konrad Krolikiewicz

  DOI：10.1016/s0040-4020(01)81518-0

  日期：1990.1
• Benzoylsalicylic acid derivatives as defense activators in tobacco and Arabidopsis
  作者：Samuel Kamatham、Reddanna Pallu、Anil Kumar Pasupulati、Surya Satyanarayana Singh、Padmaja Gudipalli

  DOI：10.1016/j.phytochem.2017.07.014

  日期：2017.11

  Systemic acquired resistance (SAR) is a long lasting inducible whole plant immunity often induced by either pathogens or chemical elicitors. Salicylic acid (SA) is a known SAR signal against a broad spectrum of pathogens in plants. In a recent study, we have reported that benzoylsalicylic acid (BzSA) is a SAR inducer in tobacco and Arabidopsis plants. Here, we have synthesized BzSA derivatives using SA and benzoyl chlorides of various moieties as substrates. The chemical structures of BzSA derivatives were elucidated using Infrared spectroscopy (IR), Nuclear magnetic spectroscopy (NMR) and High-resolution mass spectrometer (HRMS) analysis. The bioefficacy of BzSA derivatives in inducing defense response against tobacco mosaic virus (TMV) was investigated in tobacco and SA abolished transgenic NahG Arabidopsis plants. Interestingly, pre-treatment of local leaves of tobacco with BzSA derivatives enhanced the expression of SAR genes such as NPR1 [Non-expressor of pathogenesis-related (PR) genes 1], PR and other defense marker genes (HSR203, SIP1C, WIPK) in systemic leaves. Pre-treatment of BzSA derivatives reduced the spread of TMV infection to uninfected areas by restricting lesion number and diameter both in local and systemic leaves of tobacco in a dose-dependent manner. Furthermore, pre-treatment of BzSA derivatives in local leaves of SA deficient Arabidopsis NahG plants induced SAR through AtPR1 and AtPR5 gene expression and reduced leaf necrosis and curling symptoms in systemic leaves as compared to BzSA. These results suggest that BzSA derivatives are potent SAR inducers against TMV in tobacco and Arabidopsis. (C) 2017 Elsevier Ltd. All rights reserved.
• VORBRUGGEN, HELMUT;BOHN, BERNHARD D.;KROLIKIEWICZ, KONRAD, TETRAHEDRON, 46,(1990) N0, C. 3489-3502
  作者：VORBRUGGEN, HELMUT、BOHN, BERNHARD D.、KROLIKIEWICZ, KONRAD

  DOI：——

  日期：——