4-methylphenyl 3-chlorobenzoate | 6280-49-5

• 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: 4-methylphenyl 3-chlorobenzoate
• 英文别名: p-toluene m-chlorobenzoate；p-tolyl 3-chlorobenzoate；3-chloro-benzoic acid p-tolyl ester；3-Chlor-benzoesaeure-p-tolylester；3-Chlor-benzoesaeure-p-kresylester；4-Methylphenyl-3-chlorbenzoat；(4-methylphenyl) 3-chlorobenzoate
• CAS: 6280-49-5
• 化学式: C₁₄H₁₁ClO₂
• 分子量: 246.693
• InChiKey: GQGKQVFTYSXOPH-UHFFFAOYSA-N

物化性质

• 沸点：
  358.0±25.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 3-chlorobenzoate 在 三氯化铝 、 potassium carbonate 作用下， 以 硝基苯 、 丙酮 为溶剂， 反应 8.5h， 生成 ethyl [2-(3-chlorobenzoyl)-4-methylphenoxy]acetate
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of benzophenone analogues

  摘要：

  A series of substituted benzophenone analogues has been synthesized and evaluated as orally active anti-inflammatory agents with reduced side effects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin, and phenylbutazone. In carrageenan-induced foot pad edema assay, benzophenone analogues showed an interesting anti-inflammatory activity. In the air-pouch test, some of the analogues reduced the total number of leukocytes of the exudate, which indicates inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, in the liver and stomach. None of the compounds showed significant side effects compared with nonsteroidal anti-inflammatory drugs such as indomethacin and naproxen. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.04.003
• 作为产物：
  描述：

  3-chlorobenzoic 4-methylbenzoic peroxyanhydride 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-methylphenyl 3-chlorobenzoate
  参考文献：
  名称：

  在室温下将苯甲酸简单实用地转化为酚类

  摘要：

  酚类是重要的有机分子，因为它们在许多领域都有广泛的应用。本文报道了一种在室温下通过简单的有机试剂从苯甲酸制备酚类的有效实用方法。这种方法与各种官能团和杂环兼容，并且可以轻松放大。为了证明其合成效用，生物活性分子和不对称六芳基苯已通过利用这种转变作为战略步骤来制备。机理研究表明，关键的迁移步骤涉及游离碳正离子而不是自由基中间体。考虑到苯甲酸的丰富性和酚类的实用性，预计该方法将在有机合成中得到广泛的应用。

  DOI：

  10.1021/jacs.2c07529

文献信息

• Synthesis and crystallographic analysis of benzophenone derivatives—The potential anti-inflammatory agents
  作者：T.D. Venu、S. Shashikanth、S.A. Khanum、S. Naveen、Aiysha Firdouse、M.A. Sridhar、J. Shashidhara Prasad

  DOI：10.1016/j.bmc.2007.02.051

  日期：2007.5

  Fries rearrangement of substituted phenyl benzoates 1a-j to substituted hydroxy benzophenones 2a-j was achieved in excellent yield. Further benzoylation of 2a-j to benzoyloxy benzophenones 4a-n, a benzophenone analogue was achieved in good yield. All the newly synthesized compounds were evaluated for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied

  以优异的产率实现了取代苯甲酸苯酯1a-j到取代羟基二苯甲酮2a-j的弗里斯重排。2a-j进一步苯甲酰化为苯甲酰氧基二苯甲酮4a-n，二苯甲酮类似物，收率良好。评价所有新合成的化合物的抗炎活性，并与标准药物进行比较。在所研究的化合物中，对位带有氯和甲基取代基的化合物4c，4e，4g，4h和4k在所有测试剂量下均比标准药物具有更强的活性。
• Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines
  作者：Michael T. Shea、Gregory T. Rohde、Yulia A. Vlasenko、Pavel S. Postnikov、Mekhman S. Yusubov、Viktor V. Zhdankin、Akio Saito、Akira Yoshimura

  DOI：10.3390/molecules26237355

  日期：——

  Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with m-chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed

  高价碘杂环代表了一类重要的高价碘试剂，在有机合成中有许多应用。本文通过容易获得的iodobenzamides与反应报告benziodazolones的简单且方便的合成米氯过氧苯甲酸在室温下，在乙腈中。这些新的碘杂环之一的结构通过 X 射线分析得到证实。与 PPh 3和吡啶结合，这些苯并咪唑酮可以顺利地与醇或胺反应，分别生成相应的 3-氯苯甲酸酯或酰胺。发现在该酯化反应中，新型苯并碘酮试剂比类似的苯并恶酮试剂反应更有效。
• Heterogeneous catalysis by solid superacids. 17. Polymeric perfluorinated resin sulfonic acid (Nafion-H) catalyzed Fries rearrangement of aryl esters
  作者：George A. Olah、Massoud Arvanaghi、V. V. Krishnamurthy

  DOI：10.1021/jo00167a052

  日期：1983.9
• Chloro Substituted Diphenylmethanes, Phenyl Benzyl Ethers and Benzophenones Prepared from Ortho- or Para-cresol^1,2
  作者：Ralph C. Huston、Kenneth R. Robinson

  DOI：10.1021/ja01150a022

  日期：1951.6
• OLAH, G. A.;ARVANAGHI, MASSOUD;KRISHNAMURTHY, V. V., J. ORG. CHEM., 1983, 48, N 19, 3359-3360
  作者：OLAH, G. A.、ARVANAGHI, MASSOUD、KRISHNAMURTHY, V. V.

  DOI：——

  日期：——