methyl 4-carbomethoxy-2,3-dihydro-2-methylfuran-2-propanoate | 131237-56-4

• 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: methyl 4-carbomethoxy-2,3-dihydro-2-methylfuran-2-propanoate
• 英文别名: methyl 2-(3-methoxy-3-oxopropyl)-2-methyl-3H-furan-4-carboxylate
• CAS: 131237-56-4
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: KUOMGYXJKKHGKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 methyl 6a-methyl-4-oxa-3a,5,6,6a-tetrahydro-4H-cyclopentafuran-3-carboxylate 生成 methyl 4-carbomethoxy-2,3-dihydro-2-methylfuran-2-propanoate
  参考文献：
  名称：

  Studies dealing with the excited-state behavior of substituted 8-oxabicyclo[3.2.1]oct-6-en-2-ones

  摘要：

  A series of 8-oxabicyclo [3.2.1]oct-6-en-2-ones was prepared by the rhodium(II)-catalyzed cyclization-cycloaddition reaction of alpha-diazopentanedione with various alkynes. The photochemical behavior of these oxabicyclic enones was investigated. Both direct and sensitized photolysis cleanly results in a 1,3-acyl shift. A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the resulting ketene was also uncovered. The photobehavior of the closely related 9-oxabenzocycloheptene system was also examined. The initially formed 1,3-sigmatropic rearranged product was found to undergo a novel 1,4-methoxyl migration on extended photolysis. The photochemistry of the homologous 7-oxabicyclo[2.2.1]hepten-2-one was studied. The results obtained can be interpreted in terms of an initial Norrish type I cleavage. The resulting diradical either couples to give the 1,3-acyl shift product or undergoes bond fragmentation, giving products derived from a stepwise retro-Diels-Alder reaction.

  DOI：

  10.1021/jo00003a032

文献信息

• PADWA, ALBERT;ZHI, LIN;FRYXELL, GLEN E., J. ORG. CHEM., 56,(1991) N, C. 1077-1083
  作者：PADWA, ALBERT、ZHI, LIN、FRYXELL, GLEN E.

  DOI：——

  日期：——
• Studies dealing with the excited-state behavior of substituted 8-oxabicyclo[3.2.1]oct-6-en-2-ones
  作者：Albert Padwa、Lin Zhi、Glen E. Fryxell

  DOI：10.1021/jo00003a032

  日期：1991.2

  A series of 8-oxabicyclo [3.2.1]oct-6-en-2-ones was prepared by the rhodium(II)-catalyzed cyclization-cycloaddition reaction of alpha-diazopentanedione with various alkynes. The photochemical behavior of these oxabicyclic enones was investigated. Both direct and sensitized photolysis cleanly results in a 1,3-acyl shift. A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the resulting ketene was also uncovered. The photobehavior of the closely related 9-oxabenzocycloheptene system was also examined. The initially formed 1,3-sigmatropic rearranged product was found to undergo a novel 1,4-methoxyl migration on extended photolysis. The photochemistry of the homologous 7-oxabicyclo[2.2.1]hepten-2-one was studied. The results obtained can be interpreted in terms of an initial Norrish type I cleavage. The resulting diradical either couples to give the 1,3-acyl shift product or undergoes bond fragmentation, giving products derived from a stepwise retro-Diels-Alder reaction.