3-(4-苄氧基苯基)-异噁唑-5-甲醛 | 337355-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-苄氧基苯基)-异噁唑-5-甲醛
• 英文名称: 3-(4-benzyloxy-phenyl)-isoxazol-5-carbaldehyde
• 英文别名: 3-(4-Benzyloxy-phenyl)-isoxazole-5-carbaldehyde；3-(4-phenylmethoxyphenyl)-1,2-oxazole-5-carbaldehyde
• CAS: 337355-81-4
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: FHFSYUPEVSXYLG-UHFFFAOYSA-N

物化性质

• 沸点：
  491.8±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(4-苄氧基苯基)-异噁唑-5-甲醛 在 吡啶 、 三乙烯二胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.83h， 生成 Ethyl 2-[acetyloxy-[3-(4-phenylmethoxyphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enoate
  参考文献：
  名称：

  5-Isoxazolecarboxaldehyde: A Novel Substrate for Fast Baylis-Hillman Reaction

  摘要：

  3-Aryl-5-isoxazolecarboxaldehyde 与多种活化烯发生快速 Baylis-Hillman 反应，生成相应的加合物，收率极高。此处报告的一些 Baylis-Hillman 加合物随后经过改性，得到了异噁唑取代的吡唑啉-3-酮和δ-丁内酯。

  DOI：

  10.1055/s-2001-10815
• 作为产物：
  描述：

  4-benzyloxybenzaldehyde oxime 在 吡啶 、 N-氯代丁二酰亚胺 、 silica gel 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 3-(4-苄氧基苯基)-异噁唑-5-甲醛
  参考文献：
  名称：

  Synthesis and biological evaluation of novel T-type Ca2+ channel blockers

  摘要：

  A small molecule library of piperazinylalkylisoxazole derivatives containing about 600 compounds was designed, synthesized and evaluated for blocking effects on T-type Ca2+ channel. Several ligands were identified to possess high inhibitory activity against the T-type Ca2+ channel. The compound 21 with trifluoromethyl substituents at C-3-position of phenyl group (W) and C-2-position of phenyl group (R-2) showed the highest inhibitory activity with IC50 value of 1.02 muM, which is comparable to that of mibefradil. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.011

文献信息

• SUBSTITUTED AZOLE DERIVATIVES, PHARMACEUTICAL COMPOSITION CONTAINING THE DERIVATIVES, AND METHOD FOR TREATING PARKINSON'S DISEASE USING THE SAME
  申请人：Park Cheol-Hyoung

  公开号：US20110301150A1

  公开（公告）日：2011-12-08

  Provided are a substituted azole derivative and pharmaceutically acceptable salts thereof, a pharmaceutical composition including an effective amount of the derivative, and a method for treating Parkinson's disease in a mammal including administering an effective amount of the compound to the mammal. The azole derivative of the following Formula (I) and pharmaceutically useful salts thereof have an efficacy against Parkinson's disease from inhibitory effects of the activity of MAO-B.

  提供了一种替代的唑类衍生物及其药学上可接受的盐，一种包括有效量衍生物的制药组合物，以及一种治疗哺乳动物帕金森病的方法，包括向哺乳动物施用化合物的有效量。以下公式（I）的唑类衍生物及其药学上有用的盐具有抗帕金森病的功效，来自于对MAO-B活性的抑制作用。
• Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating Parkinson's disease using the same
  申请人：Park Cheol-Hyoung

  公开号：US08828992B2

  公开（公告）日：2014-09-09

  Provided are a substituted azole derivative and pharmaceutically acceptable salts thereof, a pharmaceutical composition including an effective amount of the derivative, and a method for treating Parkinson's disease in a mammal including administering an effective amount of the compound to the mammal. The azole derivative of the following Formula (I) and pharmaceutically useful salts thereof have an efficacy against Parkinson's disease from inhibitory effects of the activity of MAO-B.

  提供了一种替代的唑类衍生物及其药物可接受的盐，一种包括有效量的该衍生物的制药组合物，以及一种治疗哺乳动物帕金森病的方法，包括向哺乳动物投与有效量的该化合物。以下公式（I）的唑类衍生物及其药物可用盐对MAO-B活性的抑制作用具有有效性，可用于治疗帕金森病。
• Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity
  作者：A Patra、S Batra、A.P Bhaduri、A Khanna、R Chander、M Dikshit

  DOI：10.1016/s0968-0896(03)00105-6

  日期：2003.5

  The synthesis of isoxazole-based derivatives utilizing Baylis-Hillman chemistry and results of their preliminary bioevaluation as hypolipidemic agents in triton model are described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Baylis–Hillman reaction assisted parallel synthesis of 3,5-disubstituted isoxazoles and their in vivo bioevaluation as antithrombotic agents
  作者：S. Batra、A.K. Roy、A. Patra、A.P. Bhaduri、W.R. Surin、S.A.V. Raghavan、P. Sharma、K. Kapoor、M. Dikshit

  DOI：10.1016/j.bmc.2004.02.023

  日期：2004.5

  The solution-phase parallel synthesis involving reactions of Baylis-Hillman products of 3-substituted -5-isoxazolecarb-aldehydes with nucleophiles and their in vivo antithrombotic evaluations are described along with the results of in vitro platelet aggregation inhibition assay of a few compounds. Results of the detailed evaluation of one of the compounds as an inhibitor of platelet aggregation are also presented. (C) 2004 Elsevier Ltd. All rights reserved.
• Combinatorial synthesis and biological evaluation of isoxazole-based libraries as antithrombotic agents
  作者：S. Batra、T. Srinivasan、S.K. Rastogi、B. Kundu、A. Patra、A.P. Bhaduri、M. Dixit

  DOI：10.1016/s0960-894x(02)00333-5

  日期：2002.8

  The 3-substituted phenyl-5-isoxazolecarboxaldehydes have been identified as activated aldehydes for the generation of isoxazole-based combinatorial libraries on solid phase through automation. Three highly functionalized isoxazole-based libraries comprising of 32, 96 and 45 compounds each have been synthesized in parallel format using Baylis Hillman reaction, Michael addition, reductive amination and alkylation reactions. With an objective of lead generation all the three libraries were evaluated for their antithrombin activity in vivo. (C) 2002 Elsevier Science Ltd. All rights reserved.