4-Carbomethoxy-5-methyl-2,3-dihydrothiophene | 32595-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 4-Carbomethoxy-5-methyl-2,3-dihydrothiophene
• 英文别名: 2-Methyl-3-methoxycarbonyl-4.5-dihydrothiophen；2-Methyl-3-methoxycarbonyl-dihydro-thiophen；2-methyl-4,5-dihydro-thiophene-3-carboxylic acid methyl ester；2-Methyl-4,5-dihydro-thiophen-3-carbonsaeure-methylester；Methyl 5-methyl-2,3-dihydrothiophene-4-carboxylate
• CAS: 32595-95-2
• 化学式: C₇H₁₀O₂S
• 分子量: 158.221
• InChiKey: QJJPEOSHUVANCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Carbomethoxy-5-methyl-2,3-dihydrothiophene 在 氢氧化钾 作用下， 生成 2-Methyl-4,5-dihydro-thiophen-carbonsaeure-(3)
  参考文献：
  名称：

  Korte; Loehmer, Chemische Berichte, 1957, vol. 90, p. 1290,1293

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 2-Oxo-3-acetyl-tetrahydrothiophen 在 盐酸 作用下， 生成 4-Carbomethoxy-5-methyl-2,3-dihydrothiophene
  参考文献：
  名称：

  Korte; Loehmer, Chemische Berichte, 1957, vol. 90, p. 1290,1293

  摘要：

  DOI：

文献信息

• Dye-sensitized photooxygenation of 2,3-dihydrothiophenes: formation of stable 1,2-dioxetanes from 4,5-dialkyl-substituted derivatives
  作者：Klaus Gollnick、Karen Knutzen-Mies

  DOI：10.1021/jo00012a041

  日期：1991.6

  Singlet oxygen reacts with 4,5-dimethyl- (1a), 4-ethyl-5-methyl- (1b), and 4-isopropyl-5-methyl-2,3-dihydrothiophene (1c) to give 1,2-dioxetanes 2a-c in high yields (> 90%). 2a-c represent the first examples of sulfur-substituted dioxetanes that could be isolated. Less than 5% of allylic hydroperoxides 3a, 4a, and 3b, identified by their H-1 NMR spectra, and less than 5% of S-oxides 5a-c were formed in competing ene reactions and sulfoxide-producing steps, respectively. Due to its decreased rigidity, dioxetane 2a is less stable than its oxygen counterpart. Increased flexibility of dioxetanes derived from dihydrothiophenes and dihydrothiopyrans, as compared to those derived from dihydrofurans and dihydropyrans, causes dioxetanes 9 and 16, obtained from 4-carbomethoxy-5-methyl-2,3-dihydrothiophene (8) and 5,6-dimethyl-3,4-dihydro-2H-thiopyran (14), to cleave into dicarbonyl compounds readily at low temperatures. Sulfur-substituted allylic hydroperoxides are also less stable than their oxygen counterparts. Formation of the expected endocyclic allylic hydroperoxides 3a, 3b, and 10 is inferred from the appearance of their H2O2 elimination products, thiophenes 7a, 7b and 13, respectively.