methyl 9,10-dihydrophenanthrene-9-carboxylate | 32892-19-6

• 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: methyl 9,10-dihydrophenanthrene-9-carboxylate
• CAS: 32892-19-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: ZYXSWJFJGUXQGI-UHFFFAOYSA-N

物化性质

• 沸点：
  365.0±21.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  菲-9-甲酸 在 氨 、 lithium 作用下， 生成 methyl 9,10-dihydrophenanthrene-9-carboxylate
  参考文献：
  名称：

  Stereochemistry of 1,3-cyclohexadienes. Conformational preferences in 9-substituted 9,10-dihydrophenanthrenes

  摘要：

  DOI：

  10.1021/jo00885a015

文献信息

• Nickel-Catalyzed Three-Component [2+2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes
  作者：Zaozao Qiu、Zuowei Xie

  DOI：10.1002/anie.200902006

  日期：2009.7.20

  Three in one: Nickel‐catalyzed three‐component cycloaddition reactions of readily available arynes, activated alkenes, and alkynes gave a series of substituted 1,2‐dihydronaphthalenes in moderate to very good yields with excellent chemo‐ and regioselectivity (see scheme, TMS=trimethylsilyl, cod=1,5‐cyclooctadiene).

  三合一：镍催化的三元环加成反应可轻松获得的芳烃，活化的烯烃和炔烃，以中等至非常高的收率得到了一系列取代的1,2-二氢萘，并具有出色的化学和区域选择性（参见方案，TMS =三甲基甲硅烷基，cod = 1,5-环辛二烯）。
• σ-Bond initiated generation of aryl radicals from aryl diazonium salts
  作者：Elene Tatunashvili、Bun Chan、Philippe E. Nashar、Christopher S. P. McErlean

  DOI：10.1039/d0ob00205d

  日期：——

  transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been

  σ键亲核试剂和分子氧将芳基重氮盐转化为芳基。实验和计算研究表明，汉茨酯将氢化物转移到芳基重氮化合物上，并且氧引发了重氮中间体的自由基断裂，从而产生了芳基。在各种形成键的反应中已经说明了这种加成-断裂过程通过极性自由基交换机理产生芳基的操作简便性。
• Hanson, Peter; Loevenich, P. Wilfried; Rowell, Simon C., Journal of the Chemical Society. Perkin transactions II, 1999, # 1, p. 49 - 64
  作者：Hanson, Peter、Loevenich, P. Wilfried、Rowell, Simon C.、Walton, Paul H.、Timms, Allan W.

  DOI：——

  日期：——
• 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.
• Metal-Catalyzed Cotrimerization of Arynes and Alkenes
  作者：Iago Quintana、Arnold J. Boersma、Diego Peña、Dolores Pérez、Enrique Guitián

  DOI：10.1021/ol0611954

  日期：2006.7.1

  Cotrimerization of arynes and electron-deficient alkenes selectively affords dihydrophenanthrenes or ortho-olefinated biaryls, depending on the catalytic system employed. Our findings support a mechanism involving benzyne and a metallacycloheptadiene as key intermediates.