2-[Hydroxy-[3-(4-phenylmethoxyphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enenitrile | 337356-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[Hydroxy-[3-(4-phenylmethoxyphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enenitrile
• 英文别名: 2-[hydroxy-[3-(4-phenylmethoxyphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enenitrile
• CAS: 337356-06-6
• 化学式: C₂₀H₁₆N₂O₃
• 分子量: 332.359
• InChiKey: HRMKJEHFLZBTDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[Hydroxy-[3-(4-phenylmethoxyphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enenitrile 在 吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-2-(4-methyl-piperazin-1-ylmethyl)-acrylonitrile
  参考文献：
  名称：

  Baylis–Hillman reaction assisted parallel synthesis of 3,5-disubstituted isoxazoles and their in vivo bioevaluation as antithrombotic agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.02.023
• 作为产物：
  描述：

  丙烯腈 、 3-(4-苄氧基苯基)-异噁唑-5-甲醛 在 三乙烯二胺 作用下， 反应 0.83h， 以54%的产率得到2-[Hydroxy-[3-(4-phenylmethoxyphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enenitrile
  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

文献信息

• 5-Isoxazolecarboxaldehyde: A Novel Substrate for Fast Baylis-Hillman Reaction
  作者：Arundhati Patra、Sanjay Batra、Bijoy Kundu、Bhawani Shankar Joshi、Raja Roy、Amiya Prasad Bhaduri

  DOI：10.1055/s-2001-10815

  日期：——

  3-Aryl-5-isoxazolecarboxaldehyde undergoes fast Baylis-Hillman reaction with a variety of activated alkenes to yield the corresponding adducts in excellent yields. Some of the Baylis-Hillman adducts reported herein have been subsequently modified to obtain isoxazole substituted pyrazolin-3-ones and γ-butyrolactones.

  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。
• 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.