2-异丙氧基-5-甲基苯硼酸 | 480438-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-异丙氧基-5-甲基苯硼酸
• 中文别名: 2-异丙基-5-甲基苯硼酸；3-甲基-6-异丙氧基苯硼酸
• 英文名称: (2-isopropoxy-5-methylphenyl)boronic acid
• 英文别名: 2-Isopropoxy-5-methylphenylboronic acid；(5-methyl-2-propan-2-yloxyphenyl)boronic acid
• CAS: 480438-71-9
• 化学式: C₁₀H₁₅BO₃
• 分子量: 194.038
• InChiKey: PESPTYNENYUZTH-UHFFFAOYSA-N

物化性质

• 熔点：
  65-69 °C(lit.)
• 沸点：
  355.4±52.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  2-异丙氧基-5-甲基苯硼酸 、 N-{[3-(5-chloropyridin-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide 在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 potassium carbonate 作用下， 生成 rac-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)-N-((3-(5-(2-isopropoxy-5-methylphenyl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)benzamide
  参考文献：
  名称：

  2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Attenuation of hERG binding and improved HDLc-raising efficacy

  摘要：

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Efforts focused on finding suitable replacements for the central piperidine with the aim of reducing hERG binding: a main liability of our benchmark benzoxazole (1a). Replacement of the piperidine with a cyclohexyl group successfully attenuated hERG binding, but was accompanied by reduced in vivo efficacy. The approach of substituting a piperidine moiety with an oxazolidinone also attenuated hERG binding. Further refinement of this latter scaffold via SAR at the pyridine terminus and methyl branching on the oxazolidinone led to compounds 7e and 7f, which raised HDLc by 33 and 27 mg/dl, respectively, in our transgenic mouse PD model and without the hERG liability of previous series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.049

文献信息

• TfOH-Catalyzed Intramolecular Annulation of 2-(Aryl)-Phenyl-Substituted <i>p</i>-Quinone Methides under Continuous Flow: Total Syntheses of Selaginpulvilin I and Isoselagintamarlin A
  作者：Yogesh A. Pankhade、Rajat Pandey、Shaheen Fatma、Feroz Ahmad、Ramasamy Vijaya Anand

  DOI：10.1021/acs.joc.1c02980

  日期：2022.3.4

  1,6-conjugate arylation of 2-(aryl)-phenyl-substituted p-quinone methides (QMs) under continuous flow using the microreaction technique. This method was found to be very effective for most of the p-QMs, and the corresponding 9-aryl fluorene derivatives were obtained in moderate to excellent yields. Moreover, this protocol was further elaborated to the first total syntheses of selaginpulvilin I and isoselagintamarlin

  在本文中，我们描述了一种通过 TfOH 催化的 2-(芳基)-苯基取代的对醌甲基化物 (QM) 的分子内 1,6-共轭芳基化在连续流动下使用9-芳基芴衍生物的便捷方法。微反应技术。发现该方法对大多数p -QM非常有效，并且以中等至优异的产率获得了相应的 9-芳基芴衍生物。此外，该方案进一步阐述了selaginpulvilin I和isoselagintamarlin A的首次全合成。
• CETP INHIBITORS DERIVED FROM BENZOXAZOLE ARYLAMIDES
  申请人：Hunt Julianne A.

  公开号：US20100184719A1

  公开（公告）日：2010-07-22

  Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.

  具有公式I结构的化合物，包括化合物的药学上可接受的盐，是有效的CETP抑制剂，可用于提高HDL胆固醇，降低LDL胆固醇，并用于治疗或预防动脉粥样硬化。 在公式I中，A-B是芳香酰胺基团。
• CETP inhibitors derived from benzoxazole arylamides
  申请人：Merck Sharpe & Dohme Corp.

  公开号：US08293721B2

  公开（公告）日：2012-10-23

  Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.

  具有I式结构的化合物，包括该化合物的药物可接受的盐，是有效的CETP抑制剂，可用于提高HDL胆固醇，降低LDL胆固醇，并用于治疗或预防动脉粥样硬化。在公式I中，A-B是芳基酰胺基团。
• WO2008/156717
  申请人：——

  公开号：——

  公开（公告）日：——
• 2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy
  作者：Ramzi F. Sweis、Julianne A. Hunt、Florida Kallashi、Milton L. Hammond、Ying Chen、Suzanne S. Eveland、Qiu Guo、Sheryl A. Hyland、Denise P. Milot、Anne-Marie Cumiskey、Melanie Latham、Raymond Rosa、Larry Peterson、Carl P. Sparrow、Samuel D. Wright、Matt S. Anderson、Peter J. Sinclair

  DOI：10.1016/j.bmcl.2010.11.090

  日期：2011.3

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Initial efforts aimed at engineering replacements for the aniline substructures in the benchmark molecule. Reversing the connectivity of the central aniline lead to a new class of 2-(4-carbonylphenyl)benzoxazoles. Structure-activity studies at the C-7 and terminal pyridine ring allowed for the optimization of potency and HDLc-raising efficacy in this new class of inhibitors. These efforts lead to the discovery of benzoxazole 11v, which raised HDLc by 24 mg/dl in our transgenic mouse PD model. (C) 2010 Elsevier Ltd. All rights reserved.