1-benzyl-3-methoxy-5,7-dihydro-6,6-dioxothieno[3,4-b]pyridin-2(1H)-one | 428506-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 1-benzyl-3-methoxy-5,7-dihydro-6,6-dioxothieno[3,4-b]pyridin-2(1H)-one
• 英文别名: 1-Benzyl-3-methoxy-6,6-dioxo-5,7-dihydrothieno[3,4-b]pyridin-2-one
• CAS: 428506-71-2
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: AJQFWGOZVUWEBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-methoxy-5,7-dihydro-6,6-dioxothieno[3,4-b]pyridin-2(1H)-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以67%的产率得到1-benzyl-7-bromo-5,7-dihydro-3-methoxy-6,6-dioxothieno[3,4-b]pyridin-2(1H)-one
  参考文献：
  名称：

  Generation of 5,6-dimethylene-2(1H)-pyridinones from [3,4-b] sulfolene pyridinones and application in Diels–Alder reactions

  摘要：

  2(1H)-Pyrazinones were converted into various [3,4-b] sulfolene pyridinones 19-21, serving as precursors for thermolytic conversion into the corresponding 5,6-dimethylene 2(1 H)-pyridinone ortho-quinodimethanes. These were trapped in situ by reaction with various dienophiles. Tethering of precursor 19 with a dienophilic side chain attached to the 7-position of the [3,4-b] sulfolene pyridinone also enabled intramolecular cycloaddition when no rearrangement by 1,5-H-shift was viable. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.005
• 作为产物：
  描述：

  1-benzyl-3-methoxy-5,7-dihydrothieno[3,4-b]pyridin-2(1H)-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以80%的产率得到1-benzyl-3-methoxy-5,7-dihydro-6,6-dioxothieno[3,4-b]pyridin-2(1H)-one
  参考文献：
  名称：

  Generation of 5,6-dimethylene-2(1H)-pyridinones from [3,4-b] sulfolene pyridinones and application in Diels–Alder reactions

  摘要：

  2(1H)-Pyrazinones were converted into various [3,4-b] sulfolene pyridinones 19-21, serving as precursors for thermolytic conversion into the corresponding 5,6-dimethylene 2(1 H)-pyridinone ortho-quinodimethanes. These were trapped in situ by reaction with various dienophiles. Tethering of precursor 19 with a dienophilic side chain attached to the 7-position of the [3,4-b] sulfolene pyridinone also enabled intramolecular cycloaddition when no rearrangement by 1,5-H-shift was viable. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.005

文献信息

• Sulfolene pyridinones as precursors for pyridinone ortho -quinodimethanes and their Diels–Alder adducts
  作者：Tom C Govaerts、Ilse Vogels、Frans Compernolle、Georges Hoornaert

  DOI：10.1016/s0040-4039(01)02275-4

  日期：2002.1

  2(1H)-Pyrazinones were converted into [3,4-b] and [3,4-c] sulfolene pyridinones 4 and 5, serving as precursors for the corresponding 3.4- and 5.6-dimethylene 2(1H)-pyridinone ortho-quinodimethanes. These were trapped by in situ reaction with dienophiles. Tethering of 4 also enabled intramolecular cycloaddition. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Generation of 5,6-dimethylene-2(1H)-pyridinones from [3,4-b] sulfolene pyridinones and application in Diels–Alder reactions
  作者：Tom C Govaerts、Ilse A Vogels、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/j.tet.2003.11.005

  日期：2004.1

  2(1H)-Pyrazinones were converted into various [3,4-b] sulfolene pyridinones 19-21, serving as precursors for thermolytic conversion into the corresponding 5,6-dimethylene 2(1 H)-pyridinone ortho-quinodimethanes. These were trapped in situ by reaction with various dienophiles. Tethering of precursor 19 with a dienophilic side chain attached to the 7-position of the [3,4-b] sulfolene pyridinone also enabled intramolecular cycloaddition when no rearrangement by 1,5-H-shift was viable. (C) 2003 Elsevier Ltd. All rights reserved.