Tert-butyl 3-[5-hydroxy-4-methyl-5-(2-phenylethynyl)-2-(trifluoromethyl)-1,3-oxazol-2-yl]propanoate | 176853-36-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Tert-butyl 3-[5-hydroxy-4-methyl-5-(2-phenylethynyl)-2-(trifluoromethyl)-1,3-oxazol-2-yl]propanoate
• CAS: 176853-36-4
• 化学式: C₂₀H₂₂F₃NO₄
• 分子量: 397.394
• InChiKey: IXLOBRJEUNAAOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-[5-hydroxy-4-methyl-5-(2-phenylethynyl)-2-(trifluoromethyl)-1,3-oxazol-2-yl]propanoate 在 甲酸 作用下， 反应 12.0h， 以80%的产率得到1-苯基-1-戊炔-3,4-二酮
  参考文献：
  名称：

  Photoaddition of Alkenes to Conjugated α-Diketones:  Tandem Cyclizations Leading to Tetrasubstituted Furans^1a

  摘要：

  Photocycloaddition of 9a-c with 2 leads cleanly to tetrasubstituted furans 12a-c, respectively, in yields of similar to 85%. The reactive triplet is efficiently sensitized by 2-benzoylnaphthalene and quenched by anthracene, indicating that E(T) is in the range 43-58 kcal/mol. A mechanism is proposed involving an alkyl propargyl biradical (as 10) that closes first to a vinyl carbene (as 11) and then to product. Reaction of 9c with 20 furnishes only 22, and this result rules out an alternative mechanism in which the order of steps leading to the carbene is reversed.

  DOI：

  10.1021/jo952079+
• 作为产物：
  描述：

  4-Methyl-2-(trifluoromethyl)-1,3-oxazol-5(2H)-on 在 正丁基锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Tert-butyl 3-[5-hydroxy-4-methyl-5-(2-phenylethynyl)-2-(trifluoromethyl)-1,3-oxazol-2-yl]propanoate
  参考文献：
  名称：

  Photoaddition of Alkenes to Conjugated α-Diketones:  Tandem Cyclizations Leading to Tetrasubstituted Furans^1a

  摘要：

  Photocycloaddition of 9a-c with 2 leads cleanly to tetrasubstituted furans 12a-c, respectively, in yields of similar to 85%. The reactive triplet is efficiently sensitized by 2-benzoylnaphthalene and quenched by anthracene, indicating that E(T) is in the range 43-58 kcal/mol. A mechanism is proposed involving an alkyl propargyl biradical (as 10) that closes first to a vinyl carbene (as 11) and then to product. Reaction of 9c with 20 furnishes only 22, and this result rules out an alternative mechanism in which the order of steps leading to the carbene is reversed.

  DOI：

  10.1021/jo952079+

文献信息

• Photoaddition of Alkenes to Conjugated α-Diketones:  Tandem Cyclizations Leading to Tetrasubstituted Furans¹^a
  作者：Ashis K. Mukherjee、Paul Margaretha、William C. Agosta

  DOI：10.1021/jo952079+

  日期：1996.1.1

  Photocycloaddition of 9a-c with 2 leads cleanly to tetrasubstituted furans 12a-c, respectively, in yields of similar to 85%. The reactive triplet is efficiently sensitized by 2-benzoylnaphthalene and quenched by anthracene, indicating that E(T) is in the range 43-58 kcal/mol. A mechanism is proposed involving an alkyl propargyl biradical (as 10) that closes first to a vinyl carbene (as 11) and then to product. Reaction of 9c with 20 furnishes only 22, and this result rules out an alternative mechanism in which the order of steps leading to the carbene is reversed.