Tert-butyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate | 337355-98-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Tert-butyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate
• 英文别名: tert-butyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate
• CAS: 337355-98-3
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: PMDIPCLIJNJGMI-UHFFFAOYSA-N

物化性质

• 沸点：
  480.2±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate 在 吡啶 、 羟基甲苯磺酰碘苯 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 (3Z)-5-acetyl-3-[(3-phenyl-1,2-oxazol-5-yl)methylidene]oxolan-2-one
  参考文献：
  名称：

  Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(03)00105-6
• 作为产物：
  描述：

  3-苯基异噁唑-5-甲醛 、 丙烯酸叔丁酯 在 三乙烯二胺 作用下， 反应 0.66h， 以61%的产率得到Tert-butyl 2-[hydroxy-(3-phenyl-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

文献信息

• 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.
• The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation
  作者：A Patra、A.K Roy、B.S Joshi、R Roy、S Batra、A.P Bhaduri

  DOI：10.1016/s0040-4020(02)01561-2

  日期：2003.1

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.