2,4-dimethyl-2-(S,S-dioxidothiophen-3-yl)-4-(thiophen-3-yl)pentan-3-one | 1007097-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,4-dimethyl-2-(S,S-dioxidothiophen-3-yl)-4-(thiophen-3-yl)pentan-3-one
• 英文别名: 2-(1,1-Dioxothiophen-3-yl)-2,4-dimethyl-4-thiophen-3-ylpentan-3-one
• CAS: 1007097-85-9
• 化学式: C₁₅H₁₈O₃S₂
• 分子量: 310.438
• InChiKey: SARFXFCDJROUEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  87.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-2-(S,S-dioxidothiophen-3-yl)-4-(thiophen-3-yl)pentan-3-one 以100%的产率得到cyclobutano[4,5]thieno[3',4']-(2',2'',5',5''-tetramethyl)cyclopentanone[4''',5''']-1''',1'''-dioxothiophene
  参考文献：
  名称：

  Unexpected Solid-State Photochemistry of an α-Thiophenyl-α‘-Thiophenyl-S,S-dioxo-Substituted Ketone

  摘要：

  Samples of 2,4-dimethyl-2-(thiophen-3-yl)-4-(thiophen-3-yl-S,S-dioxo)pentan-3-one 2 were obtained by controlled MCPBA oxidation of 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one 1. Rather than the expected photodecarbonylation, UV-vis irradiation of 2 led to the intramolecular 2 + 2 photocycloaddition product 5 in quantitative yields (by GC and NMR) both in solution and in crystalline solid state. Detailed X-ray powder diffraction analyses revealed that the solid-state reaction of sulfone 2 occurs with a loss of long-range order despite retaining some birefringence under polarized microscopy.

  DOI：

  10.1021/jo702127g
• 作为产物：
  描述：

  2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以32%的产率得到2,4-dimethyl-2-(S,S-dioxidothiophen-3-yl)-4-(thiophen-3-yl)pentan-3-one
  参考文献：
  名称：

  Unexpected Solid-State Photochemistry of an α-Thiophenyl-α‘-Thiophenyl-S,S-dioxo-Substituted Ketone

  摘要：

  Samples of 2,4-dimethyl-2-(thiophen-3-yl)-4-(thiophen-3-yl-S,S-dioxo)pentan-3-one 2 were obtained by controlled MCPBA oxidation of 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one 1. Rather than the expected photodecarbonylation, UV-vis irradiation of 2 led to the intramolecular 2 + 2 photocycloaddition product 5 in quantitative yields (by GC and NMR) both in solution and in crystalline solid state. Detailed X-ray powder diffraction analyses revealed that the solid-state reaction of sulfone 2 occurs with a loss of long-range order despite retaining some birefringence under polarized microscopy.

  DOI：

  10.1021/jo702127g

文献信息

• Unexpected Solid-State Photochemistry of an α-Thiophenyl-α‘-Thiophenyl-<i>S</i>,<i>S</i>-dioxo-Substituted Ketone
  作者：Marino J. E. Resendiz、Jennifer Taing、Saeed I. Khan、Miguel A. Garcia-Garibay

  DOI：10.1021/jo702127g

  日期：2008.1.1

  Samples of 2,4-dimethyl-2-(thiophen-3-yl)-4-(thiophen-3-yl-S,S-dioxo)pentan-3-one 2 were obtained by controlled MCPBA oxidation of 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one 1. Rather than the expected photodecarbonylation, UV-vis irradiation of 2 led to the intramolecular 2 + 2 photocycloaddition product 5 in quantitative yields (by GC and NMR) both in solution and in crystalline solid state. Detailed X-ray powder diffraction analyses revealed that the solid-state reaction of sulfone 2 occurs with a loss of long-range order despite retaining some birefringence under polarized microscopy.