2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thione
• 英文别名: (1S,9R)-9-methyl-8-oxa-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene-11-thione
• 化学式: C₁₂H₁₃NOS
• 分子量: 219.307
• InChiKey: LVPAGNWZPXFPIS-PRHODGIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thione 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以35%的产率得到(+/-)-(2RS,6SR)-2,3,5,6-tetrahydro-2-methyl-2,6-methano-4H-1,3-benzoxazocin-4-one
  参考文献：
  名称：

  Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones

  摘要：

  An efficient one-pot method for the synthesis of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones in high yields has been developed via regioselective tandem reaction of coumarin-3-thioamides and ketones containing different methylene groups. Further oxidation with hydrogen peroxide under basic conditions leads to the formation of N-unsubstituted derivatives of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocin-4-one.

  DOI：

  10.1007/s10593-015-1756-8
• 作为产物：
  描述：

  2-氧代-2H-苯并吡喃-3-硫代甲酰胺 、 丙酮 在 哌啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以70%的产率得到2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thione
  参考文献：
  名称：

  Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones

  摘要：

  An efficient one-pot method for the synthesis of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones in high yields has been developed via regioselective tandem reaction of coumarin-3-thioamides and ketones containing different methylene groups. Further oxidation with hydrogen peroxide under basic conditions leads to the formation of N-unsubstituted derivatives of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocin-4-one.

  DOI：

  10.1007/s10593-015-1756-8

文献信息

• Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones
  作者：Alexander V. Borisov、Svitlana S. Kovalenko、Sergiy M. Kovalenko

  DOI：10.1007/s10593-015-1756-8

  日期：2015.7

  An efficient one-pot method for the synthesis of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones in high yields has been developed via regioselective tandem reaction of coumarin-3-thioamides and ketones containing different methylene groups. Further oxidation with hydrogen peroxide under basic conditions leads to the formation of N-unsubstituted derivatives of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocin-4-one.