1-benzyl-5-chloro-3-methoxy-6-[(2-propynylsulfonyl)methyl]-2(1H)-pyrazinone | 658071-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-benzyl-5-chloro-3-methoxy-6-[(2-propynylsulfonyl)methyl]-2(1H)-pyrazinone
• 英文别名: Nbnvavdbzaruhr-uhfffaoysa-；1-benzyl-5-chloro-3-methoxy-6-(prop-2-ynylsulfonylmethyl)pyrazin-2-one
• CAS: 658071-64-8
• 化学式: C₁₆H₁₅ClN₂O₄S
• 分子量: 366.825
• InChiKey: NBNVAVDBZARUHR-UHFFFAOYSA-N

物化性质

• 沸点：
  535.7±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-chloro-3-methoxy-6-[(2-propynylsulfonyl)methyl]-2(1H)-pyrazinone 以 甲苯 为溶剂， 反应 2.0h， 以64%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
• 作为产物：
  描述：

  1-苄基-6-溴甲基-5-氯-3-甲氧基-1H-吡嗪-2-酮 在 sodium methylate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 1-benzyl-5-chloro-3-methoxy-6-[(2-propynylsulfonyl)methyl]-2(1H)-pyrazinone
  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

• 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.

表征谱图