3-chlorophenyl 2-hydroxybenzoate | 126165-45-5

• 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: 3-chlorophenyl 2-hydroxybenzoate
• 英文别名: (3-Chlorophenyl) 2-hydroxybenzoate
• CAS: 126165-45-5
• 化学式: C₁₃H₉ClO₃
• 分子量: 248.666
• InChiKey: DSRAKPISHLDESU-UHFFFAOYSA-N

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：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chlorophenyl 2-hydroxybenzoate 以40%的产率得到
  参考文献：
  名称：

  BHAVSAR, MADHURY D.;DESAI, VIJAYKANT B., MAN-MADE TEXT. INDIA , 32,(1989) N, C. 8-11, 15

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-氯苯氧基)苯甲醛 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 三乙烯二胺 、 氧气 、 sodium iodide 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以34%的产率得到3-chlorophenyl 2-hydroxybenzoate
  参考文献：
  名称：

  N-杂环卡宾/光共催化的氧化Smiles重排：由O-芳基水杨醛合成芳基水杨酸酯。

  摘要：

  开发了N-杂环卡宾/光共催化的O-芳基水杨醛的氧化Smiles重排。缺电子的和富电子的芳基均能很好地作为迁移基团，以高收率得到相应的芳基水杨酸酯。该反应的特征是通过使用氧气作为末端氧化剂并在光催化下进行Smiles重排后，通过Breslow中间体的无金属氧化形成两个新的CO键和一个CO键断裂。

  DOI：

  10.1039/c9cc09272b

文献信息

• Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
  作者：Asik Hossian、Ranjan Jana

  DOI：10.1039/c6ob01758d

  日期：——

  We report herein, a silver(I)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C–O or C–S bond cleavage.

  我们在此报告，通过1,5-芳基迁移，通过银（I）催化的2-芳氧基-或2-（芳硫基）苯甲酸的Smiles重排以分别提供芳基-2-羟基苯甲酸酯或芳基-2-巯基苯甲酸酯二聚体。从氧或硫到羧化氧。从机理上讲，芳基醚部分受到羧基的分子内ipso攻击，然后发生C–O或C–S键断裂。芳基-2-巯基苯甲酸酯通过原位硫醇部分进行氧化二聚。
• A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids
  作者：Jose. C. Gonzalez-Gomez、Nieves P. Ramirez、Teresa Lana-Villarreal、Pedro Bonete

  DOI：10.1039/c7ob02579c

  日期：——

  We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.

  我们报告了使用可见光光氧化还原催化的2-芳氧基苯甲酸自由基Smiles重排以获得芳基水杨酸酯。该方法不含贵金属，操作简单，反应可在温和的间歇或流动条件下进行。作为氧化还原中性工艺，不需要化学计量的氧化剂或还原剂。
• Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids
  作者：Alisha Rani Tripathy、Girish Suresh Yedase、Veera Reddy Yatham

  DOI：10.1039/d1ra04130d

  日期：——

  We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3 as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.

  我们在此报道了铈光催化芳基通过自由基-Smiles重排从芳基醚迁移到羧酸基团。这种操作简单的方案利用廉价的CeCl 3作为光催化剂，并将各种2-芳氧基苯甲酸转化为芳基-2-羟基苯甲酸酯，收率良好。
• Latent mercaptan stabilizers for improved weatherability of clear halogen-containing polymer compositions
  申请人：MORTON INTERNATIONAL, INC.

  公开号：EP1004624A1

  公开（公告）日：2000-05-31

  Stabilizer compositions useful for protecting clear polyvinyl chloride and other clear halogen-containing polymer compositions used in the manufacture of exterior weatherable products against discoloration and degradation caused by exposure to ultraviolet light and weathering in addition to heat comprising a latent mercaptan which degrades during processing of the composition at an elevated temperature to liberate a free mercaptan, in combination with a synergistic amount of a free phenyl salicylate compound. The latent mercaptan may be the sole heat stabilizer additive in the stabilizer composition, but the free mercaptan released during processing may also synergize the activity of organic-based or metal-based heat stabilizers such as metal salts and organometallic stabilizers such as organotin carboxylates and organotin mercaptides in the polymer composition. Clear polyvinyl chloride and other clear halogen-containing polymer compositions containing these compounds are also provided which exhibit improved ultraviolet light stability and weatherability without detracting from their thermal performance.

  用于保护透明聚氯乙烯和其他透明含卤聚合物组合物的稳定剂组合物，这些组合物可用于制造室外耐候产品，防止因暴露于紫外线和风化以及热量而引起的褪色和降解，该组合物包括一种潜硫醇，在组合物加工过程中，该潜硫醇在高温下降解，释放出游离硫醇，并与一定量的游离水杨酸苯化合物协同作用。潜硫醇可以是稳定剂组合物中唯一的热稳定剂添加剂，但在加工过程中释放的游离硫醇也可以协同聚合物组合物中的有机基或金属基热稳定剂（如金属盐和有机金属稳定剂（如有机锡羧酸盐和有机锡硫醇盐））的活性。 此外，还提供了含有这些化合物的透明聚氯乙烯和其他透明含卤聚合物组合物，它们具有更好的紫外线稳定性和耐候性，而不会影响其热学性能。
• Stabilizers for improved weatherability of clear polyvinyl chloride compositions
  申请人：ROHM AND HAAS COMPANY

  公开号：EP1004625A1

  公开（公告）日：2000-05-31

  Stabilizer compositions that useful for protecting clear polyvinyl chloride and other clear halogenated polymer compositions against discoloration and degradation caused by exposure to light and weathering in addition to heat comprising an organotin compound selected from the group consisting of organotin mercaptides, sulfides of organotin mercaptides, organotin sulfides, and/or organotin carboxylates, and a free phenyl salicylate compound. These stabilizers offer improved ultraviolet light stability and weatherability to clear polyvinyl chloride resins designed for weatherable applications without detracting from the desired thermal performance. Clear polyvinyl chloride resin and other clear halogenated polymer compositions are also provided, containing these compounds.

  稳定剂组合物可用于保护透明聚氯乙烯和其他透明卤化聚合物组合物，防止其因受光和风化以及受热而褪色和降解，该组合物包含一种有机锡化合物，该有机锡化合物选自由有机锡硫醇、有机锡硫醇的硫化物、有机锡硫化物和/或有机锡羧酸盐以及游离水杨酸苯酯化合物组成的组。这些稳定剂提高了透明聚氯乙烯树脂的紫外线稳定性和耐候性，可用于耐候性应用，而不会影响所需的热性能。 此外，还提供了含有这些化合物的透明聚氯乙烯树脂和其他透明卤化聚合物组合物。