9,10-phenanthryne | 7048-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,10-phenanthryne
• 英文别名: Phenanthryne；Phenanthrin；9,10-Phenanthrin；9.10-Dehydrophenanthren；9,10-Didehydrophenanthrene
• CAS: 7048-96-6
• 化学式: C₁₄H₈
• 分子量: 176.218
• InChiKey: GGLLFYKEZTUKRK-UHFFFAOYSA-N

物化性质

• 沸点：
  339.1±9.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one 以 various solvent(s) 为溶剂， 生成 9,10-phenanthryne 、 Dibenzocycloheptadienocyclopropenone
  参考文献：
  名称：

  Synthesis and Photochemistry of 5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one. Generation and Reactions of Phenanthrenodiazacyclopentadiene, Phenanthrenocyclopropenone, and 9,10-Phenanthryne

  摘要：

  The title compound 15 was prepared as the first 1,3-bis(diazo) ketone incorporated into a seven-membered ring, and its photochemical pathways were investigated not only by product analysis study but also by using matrix isolation spectroscopy. Irradiation of 15 in alcoholic solvents gave 9-(alkoxycarbonyl)phenanthrene 16 as a main product, while similar irradiation in non-nucleophilic solvents provided diphenanthreno-syn-1,5-diazabicyclo[3.3.0]octadienedione (20), The formation of these products is interpreted as indicating that 15 eliminates one of two diazo functions upon photoexcitation to form 9-diazo-10-carbonylphenanthrene (21) which either reacts with alcohol by eliminating the second dinitrogen, leading to 16, or undergoes dimerization to form 20. Photolysis of 15 in an ethanol matrix at 77 K gave 9-ethoxyphenanthrene (31) as a new product along with 16. Irradiation of 15, matrix-isolated in Ar at 10 K monitored by IR, indicated that phenanthrenocyclopropenone (28) was formed as an initial product which then underwent photodecarbonylation to leave 9,10-phenanthryne (32), and that 32 reacted with CO to reproduce 28 upon photoexcitation. The cyclopropenone (28) was shown to be generated also by photolysis of 9,10-dicarboxyphenanthrene anhydride (33) in Ar matrix at 10 K. A plausible mechanism to explain the observed sequential decomposition of the two diazo functions in the room temperature photolytic run and the formal simultaneous elimination of two dinitrogens in the low temperature matrix run is proposed.

  DOI：

  10.1021/jo00113a011

文献信息

• The formation and reactions of 9,10-phenanthryne and related arynes by pyrolytic reactions in the vapor phase
  作者：Hans-Fr. Grützmacher、Udo Strabtmans

  DOI：10.1016/s0040-4020(01)93699-3

  日期：1980.1
• Synthesis and Photochemistry of 5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one. Generation and Reactions of Phenanthrenodiazacyclopentadiene, Phenanthrenocyclopropenone, and 9,10-Phenanthryne
  作者：Hideo Tomioka、Akemi Okuno、Takehiko Sugiyama、Shigeru Murata

  DOI：10.1021/jo00113a011

  日期：1995.4

  The title compound 15 was prepared as the first 1,3-bis(diazo) ketone incorporated into a seven-membered ring, and its photochemical pathways were investigated not only by product analysis study but also by using matrix isolation spectroscopy. Irradiation of 15 in alcoholic solvents gave 9-(alkoxycarbonyl)phenanthrene 16 as a main product, while similar irradiation in non-nucleophilic solvents provided diphenanthreno-syn-1,5-diazabicyclo[3.3.0]octadienedione (20), The formation of these products is interpreted as indicating that 15 eliminates one of two diazo functions upon photoexcitation to form 9-diazo-10-carbonylphenanthrene (21) which either reacts with alcohol by eliminating the second dinitrogen, leading to 16, or undergoes dimerization to form 20. Photolysis of 15 in an ethanol matrix at 77 K gave 9-ethoxyphenanthrene (31) as a new product along with 16. Irradiation of 15, matrix-isolated in Ar at 10 K monitored by IR, indicated that phenanthrenocyclopropenone (28) was formed as an initial product which then underwent photodecarbonylation to leave 9,10-phenanthryne (32), and that 32 reacted with CO to reproduce 28 upon photoexcitation. The cyclopropenone (28) was shown to be generated also by photolysis of 9,10-dicarboxyphenanthrene anhydride (33) in Ar matrix at 10 K. A plausible mechanism to explain the observed sequential decomposition of the two diazo functions in the room temperature photolytic run and the formal simultaneous elimination of two dinitrogens in the low temperature matrix run is proposed.