6,7-Dihexyl-1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene | 189636-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-Dihexyl-1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene
• 英文别名: 4,5-Dihexyl-1,8-dimethyl-11-oxatricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene
• CAS: 189636-14-4
• 化学式: C₂₄H₃₆O
• 分子量: 340.549
• InChiKey: RRSYXTNLBCENJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,7-Dihexyl-1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 8,9-Dihexyl-6,11-dimethyl-12H-benzothioxanthen
  参考文献：
  名称：

  Synthese von Benzo[b]thioxanthenen

  摘要：

  Benzo[b]thioxanthenes, heterocyclic compounds related to tetracenes and tetracyclines can be obtained by the reaction of 2H-benzo[b]thiete (1) and 1,4-naphthoquinones (3a-g). The primary cycloadducts 4a-g undergo an autoxidation process leading to the quinones 6a-g. The dihydroxy compound 4e shows an additional isomerization by a tetra-fold H transfer (4e --> 5e'). Another preparative route to benzo[b]thioxanthenes makes use of the cycloadditon reaction of 1 and 1,4-epoxynaphthalenes (7a-d). The primary adducts can be transformed to the title compounds by catalytic dehydration processes (8a-d --> 9a-d). An alternate regioselective opening of the oxygen bridge can be performed by the action of trimethyliodosilane (8a --> 10a). Methylation of 9a furnishes the sulfonium salt 14a which rearranges in a strongly alkaline medium to 16a; in the presence of oxygen ketone 17a is generated.

  DOI：

  10.1002/prac.19953370181

文献信息

• Synthesis and Stereochemistry of Diepoxynaphthacenes and Tetraepoxyheptacenes
  作者：Herbert Meier、Bernd Rose

  DOI：10.1002/jlac.199719970407

  日期：1997.4

  Cycloaddition reactions of 1,4-dihydro-1,4-epoxynaphthalenes (2) and benzo[c]furans (4), generated in situ from the tetracyclone adducts of 2, yield the diepoxynaphthacenes 5 (Schemes 1, 2). Out of 4 possible stereoisomers an exo-exo and an exo-endo geometry (A and C in Scheme 3) can be realized. The ratio A:C varies from pure A to pure C depending on the substituents of 2 and 4. Stereoisomeric heptacenes

  1，4-二氢-1，4-环氧萘（2）和苯并[ c ]呋喃（4）的环加成反应是由四环酮加合物2原位生成的，生成双环氧萘5（方案1、2）。在4种可能的立体异构体中，可以实现exo-exo和exo-endo几何形状（方案3中的A和C）。比值A：C从纯A到纯C取决于取代基而变化2和4。立体异构庚烯7可以通过相同类型的两倍环加成获得（方案4）。反应性炔烃（例如环辛炔或炔二羧酸酯）只有一个π键能够加成4（方案5、6）。
• Synthese von Benzo[b]thioxanthenen
  作者：Dieter Gr�schl、Axel Mayer、Michael Schmidt、Herbert Meier

  DOI：10.1002/prac.19953370181

  日期：——

  Benzo[b]thioxanthenes, heterocyclic compounds related to tetracenes and tetracyclines can be obtained by the reaction of 2H-benzo[b]thiete (1) and 1,4-naphthoquinones (3a-g). The primary cycloadducts 4a-g undergo an autoxidation process leading to the quinones 6a-g. The dihydroxy compound 4e shows an additional isomerization by a tetra-fold H transfer (4e --> 5e'). Another preparative route to benzo[b]thioxanthenes makes use of the cycloadditon reaction of 1 and 1,4-epoxynaphthalenes (7a-d). The primary adducts can be transformed to the title compounds by catalytic dehydration processes (8a-d --> 9a-d). An alternate regioselective opening of the oxygen bridge can be performed by the action of trimethyliodosilane (8a --> 10a). Methylation of 9a furnishes the sulfonium salt 14a which rearranges in a strongly alkaline medium to 16a; in the presence of oxygen ketone 17a is generated.