2-(4-chloro-phenyl)-4-ethoxymethylene-4H-oxazol-5-one | 353280-77-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(4-chloro-phenyl)-4-ethoxymethylene-4H-oxazol-5-one
• 英文别名: 4-ethoxymethylene-2-(4-chloro-phenyl)-4H-oxazol-5-one；4-Aethoxymethylen-2-(4-chlor-phenyl)-4H-oxazol-5-on；4-ethoxymethylene-2-p-chlorophenyl-5-azlactone；2-(p-Chlorphenyl)-4-aethoxymethylen-oxazolon-(5)；2-(4-Chlorophenyl)-4-(ethoxymethylidene)-1,3-oxazol-5-one
• CAS: 353280-77-0
• 化学式: C₁₂H₁₀ClNO₃
• 分子量: 251.669
• InChiKey: CNVAHMVIMGQUMU-UHFFFAOYSA-N

物化性质

• 沸点：
  335.3±52.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-phenyl)-4-ethoxymethylene-4H-oxazol-5-one 、 2-氨基-5-碘苯甲酸 以 乙醇 为溶剂， 生成 2-[[2-(4-chlorophenyl)-5-oxo-1,3-oxazol-4-ylidene]methylamino]-5-iodobenzoic acid
  参考文献：
  名称：

  Anthranilate 4H-oxazol-5-ones: novel small molecule antibacterial acyl carrier protein synthase (AcpS) inhibitors

  摘要：

  D-optimal design and Projection to Latent Structures (PLS) analysis were used to optimize screening hit 5 (B. subtilis AcpS IC50: 15 muM, B. subtilis MIC: >200 muM) into a series of 4H-oxazol-5-one, small molecule, antibacterial, AcpS inhibitors. Specifically, 15, 16 and 18 show muM or sub-muM AcpS inhibition (IC(50)s: 15: 1.1 muM, 16: 1.5 muM, 18: 0.27 muM) and moderate antibacterial activity (MICs: 12.5-50 muM) against B. subtilis, E. faecalis ATCC, E. faecalis VRE and S. pneumo(+). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.032
• 作为产物：
  描述：

  (4-氯苯甲酰基氨基)-乙酸 、 原甲酸三乙酯 在 乙酸酐 作用下， 生成 2-(4-chloro-phenyl)-4-ethoxymethylene-4H-oxazol-5-one
  参考文献：
  名称：

  Anthranilate 4H-oxazol-5-ones: novel small molecule antibacterial acyl carrier protein synthase (AcpS) inhibitors

  摘要：

  D-optimal design and Projection to Latent Structures (PLS) analysis were used to optimize screening hit 5 (B. subtilis AcpS IC50: 15 muM, B. subtilis MIC: >200 muM) into a series of 4H-oxazol-5-one, small molecule, antibacterial, AcpS inhibitors. Specifically, 15, 16 and 18 show muM or sub-muM AcpS inhibition (IC(50)s: 15: 1.1 muM, 16: 1.5 muM, 18: 0.27 muM) and moderate antibacterial activity (MICs: 12.5-50 muM) against B. subtilis, E. faecalis ATCC, E. faecalis VRE and S. pneumo(+). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.032

文献信息

• EP1553090
  申请人：——

  公开号：——

  公开（公告）日：——
• Syntheses of 5-Amino-2-phenyl-4(3H)-pyrimidinone Derivatives Starting with Glycine
  作者：Daisuke Takahashi、Kunisuke Izawa、Yutaka Honda

  DOI：10.3987/com-12-12432

  日期：——

  N-Cbz derivative of 5-amino-2-phenyl-4(3H)-pyrimidinone was prepared from sodium salt of methyl hydroxymethylene glycinate and benzamidine hydrochloride in good yield. However, the reaction with N-substituted benzamidine did not proceed to give the desired pyrimidinone. In contrast, the reaction of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone readily prepared from hippuric acid and N-substituted benzamidine proceeded nicely to give 5-(benzoylamino)-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid in high yield.
• Cornforth, Chemistry of Penicillin
  作者：Cornforth

  DOI：——

  日期：——
• Jena,E.; Tripathy,P.B., Journal of the Indian Chemical Society, 1970, vol. 47, p. 251 - 254
  作者：Jena,E.、Tripathy,P.B.

  DOI：——

  日期：——