2-(2-Hydroxy-2-phenyl-propyl)-oxazole-4-carboxylic acid ethyl ester | 142841-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-Hydroxy-2-phenyl-propyl)-oxazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-(2-hydroxy-2-phenylpropyl)-1,3-oxazole-4-carboxylate
• CAS: 142841-10-9
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: NPCRCLCPELFZHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-diazo-3-oxo-propanoate 在 dirhodium tetraacetate 锌 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-Hydroxy-2-phenyl-propyl)-oxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Generation and use of a zinc derivative of a functionalized 1,3-oxazole. Solution of the virginiamycin/madumycin oxazole problem

  摘要：

  2-(Bromomethyl)-4-carbethoxy-1,3-oxazole reacts with Zn dust to give a new heteroaromatic "benzylic" organozinc derivative which undergoes nucleophilic addition to a variety of aldehydes and ketones; application to the synthesis of virginiamycin and other streptogramin antibiotics is envisioned.

  DOI：

  10.1021/jo00044a009

文献信息

• Generation and use of a zinc derivative of a functionalized 1,3-oxazole. Solution of the virginiamycin/madumycin oxazole problem
  作者：Anthony R. Gangloff、Bjoern Aakermark、Paul Helquist

  DOI：10.1021/jo00044a009

  日期：1992.8

  2-(Bromomethyl)-4-carbethoxy-1,3-oxazole reacts with Zn dust to give a new heteroaromatic "benzylic" organozinc derivative which undergoes nucleophilic addition to a variety of aldehydes and ketones; application to the synthesis of virginiamycin and other streptogramin antibiotics is envisioned.