2-(3-phenyl-isoxazol-5-ylmethyl)-acrylic acid ethyl ester | 713137-97-4

• 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: 2-(3-phenyl-isoxazol-5-ylmethyl)-acrylic acid ethyl ester
• CAS: 713137-97-4
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: QBMXFOXANOOGQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 2-(3-phenyl-isoxazol-5-ylmethyl)-acrylic acid ethyl ester 以 甲醇 为溶剂， 以63%的产率得到Ethyl 2-[(4-methylpiperazin-1-yl)methyl]-3-(3-phenyl-1,2-oxazol-5-yl)propanoate
  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：

  Ethyl 2-[acetyloxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate 在 三乙烯二胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以82%的产率得到2-(3-phenyl-isoxazol-5-ylmethyl)-acrylic acid ethyl ester
  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

文献信息

• Diastereoselective Synthesis of Phosphinic Dipeptide Isosteres: Domino Chirality Transfer during a Stereocontrolled P-Michael Reaction
  作者：Angelos Lelis、Nikolaos Skoulikas、Mirto Papathanasopoulou、Kostas Voreakos、Dimitris Georgiadis

  DOI：10.1021/acs.orglett.3c02335

  日期：2023.9.15

  A highly diastereoselective P-Michael addition of chiral aminophosphinic acids to achiral acrylates has been developed, leading to phosphinic dipeptide isosteres in high yields and dr of up to >50:1. The method allows for the diastereoselective preparation of target compounds without the need for chiral auxiliaries or P-chiral substrates. A possible mechanistic explanation involves a domino chirality

  已开发出手性氨基次膦酸与非手性丙烯酸酯的高度非对映选择性 P-Michael 加成反应，可产生高产率的次膦二肽电子等排体，dr 高达 >50:1。该方法允许非对映选择性制备目标化合物，而不需要手性助剂或 P-手性底物。一种可能的机制解释涉及从氨基次膦酸到 P 中心的多米诺骨牌手性转移，通过关键的二苯甲基酯基团放大，然后转移到 α-碳。