1-(Acetylthio)-4-methyl-3-pentanone | 133966-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(Acetylthio)-4-methyl-3-pentanone
• 英文别名: S-(4-methyl-3-oxopentyl) ethanethioate
• CAS: 133966-48-0
• 化学式: C₈H₁₄O₂S
• 分子量: 174.264
• InChiKey: NZLIHAKBLIICEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-Isopropyl-5-methyl-2,3-dihydrothiophene 在 氧气 、 tetraphenylporphyrin 作用下， 以 氘代氯仿 、 一氟三氯甲烷 为溶剂， 反应 3.0h， 生成 1-(Acetylthio)-4-methyl-3-pentanone
  参考文献：
  名称：

  Dye-sensitized photooxygenation of 2,3-dihydrothiophenes: formation of stable 1,2-dioxetanes from 4,5-dialkyl-substituted derivatives

  摘要：

  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.

  DOI：

  10.1021/jo00012a041