2-(tert-butylthio)-1,4-benzoquinone | 113679-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(tert-butylthio)-1,4-benzoquinone
• 英文别名: 2-(tert-Butylsulfanyl)cyclohexa-2,5-diene-1,4-dione；2-tert-butylsulfanylcyclohexa-2,5-diene-1,4-dione
• CAS: 113679-39-3
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: DIWBYKBPDGOSMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butylthio)-1,4-benzoquinone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(SS*)-2-(tert-butylsulfinyl)-1,4-benzoquinone
  参考文献：
  名称：

  On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran

  摘要：

  A mechanistic study of the reactions between 2-trimethyisilyloxyfuran 1 and (SS)-2-(arylsulfinyl)- 1,4-benzoquinones 2a and 2b, giving rise to the diastereoselective formation of [3aS,8bS,SS]-3a,8b-dihydro-7-hydroxy-8-(arylsulfinyl)furo[3,2-b]benzofuran-2(3H)-ones 3a and 3b, is reported. The detection and H-1 NMR characterization of several precursors of 3a and 3b accounts for a Michael-type initial reaction which dictates the final diastereoselection of the process. A significant improvement of the stereoselectivity (up to 96% de) in the formation of the tert-butylsulfinyl substituted derivative 3c was achieved by using 2-(tert-butylsulfinyl)- 1,4-benzoquinone 2c as the starting quinone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00460-7
• 作为产物：
  描述：

  叔丁基硫醇 、 对苯醌 以 乙醇 为溶剂， 反应 4.0h， 以50%的产率得到2-(tert-butylthio)-1,4-benzoquinone
  参考文献：
  名称：

  On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran

  摘要：

  A mechanistic study of the reactions between 2-trimethyisilyloxyfuran 1 and (SS)-2-(arylsulfinyl)- 1,4-benzoquinones 2a and 2b, giving rise to the diastereoselective formation of [3aS,8bS,SS]-3a,8b-dihydro-7-hydroxy-8-(arylsulfinyl)furo[3,2-b]benzofuran-2(3H)-ones 3a and 3b, is reported. The detection and H-1 NMR characterization of several precursors of 3a and 3b accounts for a Michael-type initial reaction which dictates the final diastereoselection of the process. A significant improvement of the stereoselectivity (up to 96% de) in the formation of the tert-butylsulfinyl substituted derivative 3c was achieved by using 2-(tert-butylsulfinyl)- 1,4-benzoquinone 2c as the starting quinone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00460-7