S-(1-methoxy-2,2,4,4-tetramethyl-3-oxopentyl) 3-methoxybenzenecarbothioate | 1207993-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(1-methoxy-2,2,4,4-tetramethyl-3-oxopentyl) 3-methoxybenzenecarbothioate
• CAS: 1207993-72-3
• 化学式: C₁₈H₂₆O₄S
• 分子量: 338.468
• InChiKey: ITHOJGXIEORIGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,3R,5S)-5-tert-butyl-3-methoxy-1-(3-methoxyphenyl)-4,4-dimethyl-6,7-dioxa-2-thiabicyclo[3.2.0]heptane 以 甲苯 为溶剂， 反应 1.0h， 生成 S-(1-methoxy-2,2,4,4-tetramethyl-3-oxopentyl) 3-methoxybenzenecarbothioate
  参考文献：
  名称：

  Synthesis of Sulfanyl-, Sulfinyl-, and Sulfonyl-Substituted Bicyclic Dioxetanes and Their Base-Induced Chemiluminescence

  摘要：

  The singlet oxygenation of 4-tert-butyl-3,3-dimethyl-5-(3-oxyphenyl)-2,3-dihydrothiophenes 5c-e bearing an acetoxy or methoxy group at the 2-position exclusively gave the corresponding sulfanyl-substituted bicyclic dioxetanes 2c-e, while that of 5a without 2-substituent mainly gave sulfoxide 11 along with a small amount of dioxetane 2a. These dioxetanes were sufficiently stable thermally to permit handling at room temperature. Sulfanyl-substituted dioxetanes, 2e and 2e, were further oxidized with m-chloroperberizoic acid to afford the corresponding sulfinyl-substituted dioxetanes 3c, 3e and sulfonyl-substituted dioxetanes 4c, 4e. X-ray single crystallographic analysis was performed for 2c and 4e. Base-induced decomposition of the dioxetanes in DMSO gave light with a maximum wavelength lambda(CL)(max) at 554 nm for 2a and 565 nm for 2e in moderate light yields, while sulfinyl-derivative 3e gave weak light with lambda(CL)(max) = 795 nm and sulfonyl-derivative 4e gave very weak light with lambda(CL)(max) = 848 nm.

  DOI：

  10.1021/jo902477n