3-acetoxydibenzothiophene | 69747-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-acetoxydibenzothiophene
• 英文别名: dibenzothiophen-3-yl acetate
• CAS: 69747-76-8
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: MWPSOALMAMABMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  二苯并噻吩 、 溶剂黄146 在 2,2'-联吡啶 、 sodium persulfate 、 silver tetrafluoroborate 、 sodium acetate 作用下， 反应 16.0h， 生成 3-acetoxydibenzothiophene 、 4-acetoxydibenzothiophene 、 1-acetoxydibenzothiophene
  参考文献：
  名称：

  Regiochemistry of the Reaction between Dibenzothiophene Radical Cation and Nucleophiles or Nitrogen Dioxide.

  摘要：

  The regiochemistry of nucleophile or radical attack upon dibenzothiophene radical cation (2(.+)) has been studied, using the photolysis of 2-tetranitromethane, the NO2 or nitrous acid catalyzed (NAC) nitration of 2 and the silver(II) mediated acetoxylation of 2 as test reactions in all likelihood mediated by 2(.+). The results are discussed in relation to theoretical predictions based on the VBCM model.The photolysis of the charge-transfer complex of 2 and tetranitromethane in dichloromethane gives mainly dibenzothiophene sulfoxide (3) and minor amounts of 2-nitrodibenzothiophene (4), r-1-hydroxy-c-4-trinitromethyl-1,4-dihydrodibenzothiophene (5), t-2-nitro-r-1-trinitromethyl-1,2-dihydrodibenzothiophene (6) and c-1-nitro-r-4-trinitromethyl-1,4-dihydro-dibenzothiophene 7. In acetonitrile the major product is the sulfoxide 3 together with 2-nitrodibenzothiophene (4) and 4-nitrodibenzothiophene (9). The photolysis in 1,1,1,3,3,3-hexafluoropropan-2-ol yields only the sulfoxide 3 and minor amounts of the 2-nitroarene 4.Nitration of 2 by NO, in dichloromethane gives largely 3 and the 2-nitro isomer 4, as does NAC nitration in acetic acid.The oxidation of 2 by an Ag-II complex of 2,2'-bipyridine gave mainly 1- and 4-acetoxydibenzothiophene and a minor proportion of the 3-acetoxy isomer, no sulfoxide 3 being formed.The X-ray crystal structure is reported for compound 5.

  DOI：

  10.3891/acta.chem.scand.51-0839

文献信息

• Regiochemistry of the Reaction between Dibenzothiophene Radical Cation and Nucleophiles or Nitrogen Dioxide.
  作者：Craig P. Butts、Lennart Eberson、Michael P. Hartshorn、Finn Radner、Ward T. Robinson、Bryan R. Wood、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0839

  日期：——

  The regiochemistry of nucleophile or radical attack upon dibenzothiophene radical cation (2(.+)) has been studied, using the photolysis of 2-tetranitromethane, the NO2 or nitrous acid catalyzed (NAC) nitration of 2 and the silver(II) mediated acetoxylation of 2 as test reactions in all likelihood mediated by 2(.+). The results are discussed in relation to theoretical predictions based on the VBCM model.The photolysis of the charge-transfer complex of 2 and tetranitromethane in dichloromethane gives mainly dibenzothiophene sulfoxide (3) and minor amounts of 2-nitrodibenzothiophene (4), r-1-hydroxy-c-4-trinitromethyl-1,4-dihydrodibenzothiophene (5), t-2-nitro-r-1-trinitromethyl-1,2-dihydrodibenzothiophene (6) and c-1-nitro-r-4-trinitromethyl-1,4-dihydro-dibenzothiophene 7. In acetonitrile the major product is the sulfoxide 3 together with 2-nitrodibenzothiophene (4) and 4-nitrodibenzothiophene (9). The photolysis in 1,1,1,3,3,3-hexafluoropropan-2-ol yields only the sulfoxide 3 and minor amounts of the 2-nitroarene 4.Nitration of 2 by NO, in dichloromethane gives largely 3 and the 2-nitro isomer 4, as does NAC nitration in acetic acid.The oxidation of 2 by an Ag-II complex of 2,2'-bipyridine gave mainly 1- and 4-acetoxydibenzothiophene and a minor proportion of the 3-acetoxy isomer, no sulfoxide 3 being formed.The X-ray crystal structure is reported for compound 5.