4-phenyl-2-(phenylimino)-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine | 135192-07-3

• 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: 4-phenyl-2-(phenylimino)-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine
• CAS: 135192-07-3
• 化学式: C₂₃H₂₀N₂OS
• 分子量: 372.491
• InChiKey: VNEWJKSEBDPVAH-FCEUIQTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  33.62
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-(phenylimino)-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine 、 碘甲烷 在 sodium hydride 作用下， 生成 2-(N-methyl-N-phenylamino)-4-phenyl-3,4,4a,10b-tetrahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions of 1-thia-3-azabutadienes. One-pot synthesis of annulated thiazines from N-(trimethylsilyl)imines and isothiocyanates

  摘要：

  The intramolecular [4 + 2] cycloaddition of 1-thia-3-aza dienes is described. Substituted N-(trimethylsilyl)imines 2 derived from aromatic and heteroaromatic aldehydes 1 react with isothiocyanates to form heterodienes 3, which, although not isolated, undergo intramolecular cycloaddition at 90-degrees-C to yield heteropolycyclic compounds 5 and 7. The process was found to be regioselective and stereospecific; the stereochemistry of the cycloadducts arises from an exo transition state.

  DOI：

  10.1021/jo00019a040
• 作为产物：
  描述：

  2-(3-苯基丙-2-烯氧基)苯甲醛 、 硫代异氰酸苯酯 生成 4-phenyl-2-(phenylimino)-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions of 1-thia-3-azabutadienes. One-pot synthesis of annulated thiazines from N-(trimethylsilyl)imines and isothiocyanates

  摘要：

  The intramolecular [4 + 2] cycloaddition of 1-thia-3-aza dienes is described. Substituted N-(trimethylsilyl)imines 2 derived from aromatic and heteroaromatic aldehydes 1 react with isothiocyanates to form heterodienes 3, which, although not isolated, undergo intramolecular cycloaddition at 90-degrees-C to yield heteropolycyclic compounds 5 and 7. The process was found to be regioselective and stereospecific; the stereochemistry of the cycloadducts arises from an exo transition state.

  DOI：

  10.1021/jo00019a040