2-phenyl-5H-5,9b[1′,2′]-benzothieno[3,2-c]isoquinoline 4-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-phenyl-5H-5,9b[1′,2′]-benzothieno[3,2-c]isoquinoline 4-oxide
• 英文别名: 19-Oxido-16-phenyl-15-thia-19-azoniapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,16,18-octaene；19-oxido-16-phenyl-15-thia-19-azoniapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,16,18-octaene
• 化学式: C₂₃H₁₅NOS
• 分子量: 353.444
• InChiKey: NPHBALHTDSOESZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-5H-5,9b[1′,2′]-benzothieno[3,2-c]isoquinoline 4-oxide 、 三(五氟苯基)硼烷 以 二氯甲烷 为溶剂， 反应 15.0h， 以95%的产率得到(2-phenyl-5H-5,9b[1′,2′]benzothieno[3,2-c]isoquinoline 4-oxide)tris(pentafluorophenyl)borane
  参考文献：
  名称：

  Synthesis of 4-Chalcogeno-1-aza-1,3-butadiene Derivatives by Intramolecular Cyano-Diels–Alder Reaction and Borane-Coordination-Induced Fluorescence Enhancement

  摘要：

  4-Thio-1-aza-1,3-butadiene derivatives 3 incorporating a rigid dibenzobarrelene skeleton were synthesized by the intramolecular cyano-Diels-Alder reaction of 9-anthryl cyanoethenyl sulfides 6. The thermal reaction of 6 afforded an equilibrium mixture of 3 and 6, but the cyclization was effectively promoted by the addition of BF3·Et2O or B(C6F5)3 to yield imine-borane adducts 8 and 9. The imine-borane adducts emit intense blue fluorescence both in solution and in the crystalline state. This is in stark contrast to free imines 3, which are weakly fluorescent. Selenium analogue 4 and N-oxide 12 of 3a were synthesized, along with their B(C6F5)3 adducts.

  DOI：

  10.1021/jo501103e
• 作为产物：
  描述：

  3-苯基丙炔腈 在 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 61.0h， 生成 2-phenyl-5H-5,9b[1′,2′]-benzothieno[3,2-c]isoquinoline 4-oxide
  参考文献：
  名称：

  Synthesis of 4-Chalcogeno-1-aza-1,3-butadiene Derivatives by Intramolecular Cyano-Diels–Alder Reaction and Borane-Coordination-Induced Fluorescence Enhancement

  摘要：

  4-Thio-1-aza-1,3-butadiene derivatives 3 incorporating a rigid dibenzobarrelene skeleton were synthesized by the intramolecular cyano-Diels-Alder reaction of 9-anthryl cyanoethenyl sulfides 6. The thermal reaction of 6 afforded an equilibrium mixture of 3 and 6, but the cyclization was effectively promoted by the addition of BF3·Et2O or B(C6F5)3 to yield imine-borane adducts 8 and 9. The imine-borane adducts emit intense blue fluorescence both in solution and in the crystalline state. This is in stark contrast to free imines 3, which are weakly fluorescent. Selenium analogue 4 and N-oxide 12 of 3a were synthesized, along with their B(C6F5)3 adducts.

  DOI：

  10.1021/jo501103e

文献信息

• Synthesis of 4-Chalcogeno-1-aza-1,3-butadiene Derivatives by Intramolecular Cyano-Diels–Alder Reaction and Borane-Coordination-Induced Fluorescence Enhancement
  作者：Akihiko Ishii、Yutaro Aoki、Norio Nakata

  DOI：10.1021/jo501103e

  日期：2014.9.5

  4-Thio-1-aza-1,3-butadiene derivatives 3 incorporating a rigid dibenzobarrelene skeleton were synthesized by the intramolecular cyano-Diels-Alder reaction of 9-anthryl cyanoethenyl sulfides 6. The thermal reaction of 6 afforded an equilibrium mixture of 3 and 6, but the cyclization was effectively promoted by the addition of BF3·Et2O or B(C6F5)3 to yield imine-borane adducts 8 and 9. The imine-borane adducts emit intense blue fluorescence both in solution and in the crystalline state. This is in stark contrast to free imines 3, which are weakly fluorescent. Selenium analogue 4 and N-oxide 12 of 3a were synthesized, along with their B(C6F5)3 adducts.