5-(3-acetoxyphenyl)-4-tert-butyl-2-methoxy-3,3-dimethyl-2,3-dihydrothiophene | 1207993-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 5-(3-acetoxyphenyl)-4-tert-butyl-2-methoxy-3,3-dimethyl-2,3-dihydrothiophene
• 英文别名: [3-(4-tert-butyl-2-methoxy-3,3-dimethyl-2H-thiophen-5-yl)phenyl] acetate
• CAS: 1207993-62-1
• 化学式: C₁₉H₂₆O₃S
• 分子量: 334.48
• InChiKey: LTZFFDCOWSRCCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-acetoxyphenyl)-4-tert-butyl-2-methoxy-3,3-dimethyl-2,3-dihydrothiophene 在 氧气 、 亚甲兰 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以85%的产率得到1-(3-acetoxyphenyl)-5-tert-butyl-3-methoxy-4,4-dimethyl-6,7-dioxa-2-thiabicyclo[3.2.0]heptane
  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
• 作为产物：
  描述：

  4-tert-butyl-5-(3-hydroxyphenyl)-2-methoxy-3,3-dimethyl-2,3-dihydrothiophene 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到5-(3-acetoxyphenyl)-4-tert-butyl-2-methoxy-3,3-dimethyl-2,3-dihydrothiophene
  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