N,N-diethyl-9-phenanthrenecarboxamide | 87166-89-0

• 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: N,N-diethyl-9-phenanthrenecarboxamide
• 英文别名: N,N-diethylphenanthrene-9-carboxamide；9-(N,N-Diethylcarbamoyl)phenanthrene
• CAS: 87166-89-0
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: KENRRSRYMMXYAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-9-phenanthrenecarboxamide 在 platinum(IV) oxide 氢氧化钾 、 氢气 、 铜 、 锌 作用下， 以 吡啶 、 水 为溶剂， 反应 30.5h， 生成 10,11,12,13,13a,14-Hexahydro-9a-aza-benzo[b]triphenylen-9-one
  参考文献：
  名称：

  定向芳香族叔金属的邻位金属化：一种新的n杂化环化方法以及菲咯啉喹啉和吲哚并立生物碱的合成

  摘要：

  描述了通过普通菲（1）的定向邻位金属化反应合成菲咯啉-喹唑烷和-吲哚唑烷生物碱，隐藻碱（8）和antofine（9）（方案2）。此策略为新的N-杂环成环方法（所述的实用方案1）由其他芳族环稠合的喹嗪啶（制备图示12,15）和吲哚里（18，21）的系统。报道了一种用于Li过渡金属化的Mg，它对于13的合成至关重要，并且在定向金属化化学中具有潜在的更广泛的意义。

  DOI：

  10.1016/s0040-4020(01)91913-1
• 作为产物：
  描述：

  菲-9-甲酸 、 二乙胺 在 草酰氯 作用下， 生成 N,N-diethyl-9-phenanthrenecarboxamide
  参考文献：
  名称：

  定向芳香族叔金属的邻位金属化：一种新的n杂化环化方法以及菲咯啉喹啉和吲哚并立生物碱的合成

  摘要：

  描述了通过普通菲（1）的定向邻位金属化反应合成菲咯啉-喹唑烷和-吲哚唑烷生物碱，隐藻碱（8）和antofine（9）（方案2）。此策略为新的N-杂环成环方法（所述的实用方案1）由其他芳族环稠合的喹嗪啶（制备图示12,15）和吲哚里（18，21）的系统。报道了一种用于Li过渡金属化的Mg，它对于13的合成至关重要，并且在定向金属化化学中具有潜在的更广泛的意义。

  DOI：

  10.1016/s0040-4020(01)91913-1

文献信息

• Connections to the died ortho metalation strategy. Pd(0)-catalyzed cross coupling of aryl boronic acids with aryl triflatest
  作者：J.-m. Fu、V. Snieckus

  DOI：10.1016/s0040-4039(00)88848-6

  日期：1990.1
• 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.
• WANG, X.;SNIECKUS, V., SYNLETT.,(1990) N, C. 313-316
  作者：WANG, X.、SNIECKUS, V.

  DOI：——

  日期：——
• Directed ortho metallation of tertiary aromatic amides
  作者：M. Iwao、K.K. Mahalanabis、M. Watanabe、S.O. De Silva、V. Snieckus

  DOI：10.1016/s0040-4020(01)91913-1

  日期：1983.1

  cryptopleurine (8) and antofine (9) via directed ortho metallation of the common phenanthrene (1) are described (Scheme 2). The utility of this strategy as a new N-heteroring annelation method (Scheme 1) is illustrated by the preparation of other aromatic ring-fused quinolizidine (12,15) and indolizidine (18,21) systems. A Mg for Li transmetallation, crucial for the synthesis of 13 and of potential broader

  描述了通过普通菲（1）的定向邻位金属化反应合成菲咯啉-喹唑烷和-吲哚唑烷生物碱，隐藻碱（8）和antofine（9）（方案2）。此策略为新的N-杂环成环方法（所述的实用方案1）由其他芳族环稠合的喹嗪啶（制备图示12,15）和吲哚里（18，21）的系统。报道了一种用于Li过渡金属化的Mg，它对于13的合成至关重要，并且在定向金属化化学中具有潜在的更广泛的意义。