o-phenol | 78154-49-1

• 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: o-phenol
• 英文别名: 3-chloro-benzoic acid-(2-hydroxy-anilide)；3-Chlor-benzoesaeure-(2-hydroxy-anilid)；3-chloro-N-(2-hydroxyphenyl)benzamide
• CAS: 78154-49-1
• 化学式: C₁₃H₁₀ClNO₂
• 分子量: 247.681
• InChiKey: FWMLPYBEDRLHKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C
• 沸点：
  319.8±27.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-phenol 在 Al³⁺ exchanged K₁₀ clay 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 16.0h， 以98%的产率得到2-(3-氯苯基)-1,3-苯并恶唑
  参考文献：
  名称：

  A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay

  摘要：

  A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives are synthesized in high yields without affecting many functional groups. Hot filtration experiments showed the absence of metal leaching and catalyst can be reused for five times with only a slight decrease in yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.039
• 作为产物：
  描述：

  11-hydroxytetrahydrocarbazolenine 在 silica gel 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 o-phenol
  参考文献：
  名称：

  Hino, Tohru; Yamaguchi, Hitoshi; Matsuki, Kenji, Journal of the Chemical Society. Perkin transactions I, 1983, # 1, p. 141 - 146

  摘要：

  DOI：

文献信息

• Tertiary Amine-Catalyzed Acyl Group Exchange Reaction of<i>N</i>,<i>O</i>-Diacyl-<i>o</i>-aminophenols. Its Mechanism and Factors Determining the Relative Stability of Acyl Exchanged Isomer Pairs
  作者：Tadamitsu Sakurai、Shuichi Kojima、Hiroyasu Inoue

  DOI：10.1246/bcsj.63.3141

  日期：1990.11

  polarities. It was found that the relative stability of acyl exchanged isomer pairs is determined solely by the inductive effect of acyl groups, provided that the steric hindrance of acyl substituents bonded to amide nitrogen affects the stability to the same extent. The importance of steric hindrance exerted by a bulky acyl group in determining the relative stability was demonstrated by analyzing the

  已经在不同极性的溶剂中研究了酰基取代基对各种 N,O-二酰基-o-氨基苯酚的酰基交换反应的平衡和速率常数的影响。发现酰基交换的异构体对的相对稳定性仅由酰基的诱导作用决定，条件是与酰胺氮键合的酰基取代基的空间位阻对稳定性产生相同程度的影响。通过分析标准自由能变化 (ΔG°) 和 pKa 之间的相关性，证明了由庞大的酰基施加的空间位阻在确定相对稳定性方面的重要性，标准自由能变化 (ΔG°) 和 pKa 用作异构体对的相对稳定性的量度和分别为酰基的吸电子能力。另一方面，酰基迁移反应的催化速率常数的对数与 pKa 值密切相关。除了这个发现之外，激活熵的大负值 ΔS\eweq=...
• A Rearrangement of 4-Phenylbenzo[d]oxazoles to Phenanthridin-4-ols
  作者：Alexander S. Fisyuk、Anton L. Shatsauskas、Ekaterina S. Keyn、Anton J. Stasyuk、Sergey A. Kirnosov、Vladislav Yu. Shuvalov、Anastasia S. Kostyuchenko

  DOI：10.1055/a-2193-5593

  日期：2024.2

  A new approach was developed for the synthesis of phenanthridin-4-ols and 4-hydroxyphenanthridin-6(5H)-one derivatives in 43–89% yields based on the AlCl3-mediated rearrangement of available 4-phenylbenzo[d]oxazoles and 4-phenyl-1,3-benzoxazol-2(3H)-one. The quantum chemical calculations were used to describe the mechanism and predict the thermodynamic parameters of the reaction under study.

  基于 AlCl3 介导的 4-苯基苯并[d]恶唑和 4 的重排，开发了一种合成菲啶-4-醇和 4-羟基菲啶-6(5H)-酮衍生物的新方法，产率为 43-89%。 -苯基-1,3-苯并恶唑-2(3H)-酮。量子化学计算用于描述机理并预测所研究反应的热力学参数。
• Supported Pd-catalyzed ring opening and chemoselective aminocarbonylative coupling of benzoxazoles with aryl iodides
  作者：Pushkar Mehara、Ajay Kumar Sharma、Ashish Kumar、Poonam Sharma、Pralay Das

  DOI：10.1039/d4cy00070f

  日期：——

  A tandem approach using polystyrene supported Pd catalyzed ring opening aminocarbonylative coupling of benzoxazoles with aryl iodides has been developed for the synthesis of N-(2-hydroxyphenyl)benzamides using solid oxalic acid as the CO source.

  以固体草酸为 CO 源，开发了一种串联方法，利用聚苯乙烯支撑的钯催化苯并恶唑与芳基碘化物的开环氨基羰基偶联合成 N-(2-羟基苯基)苯甲酰胺。
• Biochemical and Structural Evaluation of Highly Selective 2-Arylbenzoxazole-Based Transthyretin Amyloidogenesis Inhibitors
  作者：Steven M. Johnson、Stephen Connelly、Ian A. Wilson、Jeffery W. Kelly

  DOI：10.1021/jm0708735

  日期：2008.1.1

  To develop potent transthyretin (TTR) amyloidogenesis inhibitors that also display high binding selectivity in blood, it proves useful to systematically optimize each of the three substructural elements that comprise a typical inhibitor: the two aryl rings and the linker joining them. In the first study, described herein, structural modifications to one aryl ring were evaluated by screening a library of 2-arylbenzoxazoles bearing thyroid hormone-like aryl substituents on the 2-aryl ring. Several potent and highly selective amyloidogenesis inhibitors were identified that exhibit minimal thyroid hormone nuclear receptor and COX-1 binding. High resolution crystal structures (1.3-1.5 angstrom) of three inhibitors (2f, 4f, and 4d) in complex with TTR were obtained to characterize their binding orientation. Collectively, the results demonstrate that thyroid hormone-like substitution patterns on one aryl ring lead to potent and highly selective TTR amyloidogenesis inhibitors that lack undesirable thyroid hormone receptor or COX-1 binding.
• ACYL DERIVATIVES OF ORTHO-AMINOPHENOL. VI
  作者：C. B. Pollard、R. E. Nelson

  DOI：10.1021/ja01354a023

  日期：1931.3