2-(ethylimino)-4-phenyl-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine | 135192-09-5

• 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-(ethylimino)-4-phenyl-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine
• 英文别名: (4S,4aR,10bR)-N-ethyl-4-phenyl-4,4a,5,10b-tetrahydro-1H-chromeno[4,3-d][1,3]thiazin-2-imine
• CAS: 135192-09-5
• 化学式: C₁₉H₂₀N₂OS
• 分子量: 324.447
• InChiKey: BNMHITPNRHGPDI-RYQLBKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-苯基丙-2-烯氧基)苯甲醛 、 异硫氰酸乙酯 生成 2-(ethylimino)-4-phenyl-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

文献信息

• Intramolecular Diels-Alder reactions of 1-thia-3-azabutadienes. One-pot synthesis of annulated thiazines from N-(trimethylsilyl)imines and isothiocyanates
  作者：Jose Barluenga、Miguel Tomas、Alfredo Ballesteros、Luis A. Lopez

  DOI：10.1021/jo00019a040

  日期：1991.9

  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.