6-Benzoylperimidin | 56314-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Benzoylperimidin
• 英文别名: 6(7)-benzoylperimidine；(1(3)H-perimidin-6-yl)-phenyl-methanone
• CAS: 56314-41-1
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: BTNIOSVCPNBPKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-Benzoylperimidin 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 反应 1.0h， 以83%的产率得到6-benzoyl-2,3-dihydroperimidine
  参考文献：
  名称：

  Synthesis of 2,3-dihydroperimidine ketones

  摘要：

  Ketones derived from unsubstituted 2,3-dihydroperimidine were obtained by the selective reduction of the corresponding acylperimidines. The direct acylation of 2,3-dihydroperimidine in PPA is accompanied by dehydrogenation and leads to 4(9)-acylperimidines. The spectral characteristics of these products were discussed.

  DOI：

  10.1007/s10593-009-0325-4
• 作为产物：
  描述：

  呸啶 、 苯甲酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到6-Benzoylperimidin
  参考文献：
  名称：

  Synthesis of 2,3-dihydroperimidine ketones

  摘要：

  Ketones derived from unsubstituted 2,3-dihydroperimidine were obtained by the selective reduction of the corresponding acylperimidines. The direct acylation of 2,3-dihydroperimidine in PPA is accompanied by dehydrogenation and leads to 4(9)-acylperimidines. The spectral characteristics of these products were discussed.

  DOI：

  10.1007/s10593-009-0325-4

文献信息

• A facile and efficient synthesis of<i>N</i>-substituted furo[3,4-<i>b</i>]indeno[2,1-<i>e</i>]pyridine analogues of azapodophyllotoxin<i>via</i>microwave-assisted multicomponent reactions
  作者：Feng Shi、Ge Zhang、Yan Zhang、Ning Ma、Bo Jiang、Shu-Jiang Tu

  DOI：10.1002/jhet.187

  日期：2009.9

  The efficient and facile synthesis of N-substituted furo[3,4-b]indeno[2,1-e]pyridine analogues of azapodophyllotoxin was achieved via microwave-assisted multicomponent reactions of aldehyde, 2H-indene-1,3-dione and 4-(arylamino)furan-2(5H)-one in glycol without catalyst. This method has the obvious advantages over traditional heating ones on short reaction time, high yield, operational simplicity as

  的有效和简便合成ñ -取代呋喃并[3,4- b ]茚并[2,1- ë ]吡啶azapodophyllotoxin类似物达到通过微波辅助的多组分反应的醛，在没有催化剂的情况下在乙二醇中的2 H-茚-1,3-二酮和4-（芳基氨基）呋喃-2（5 H）-1 。与传统的加热方法相比，该方法具有明显的优势，即反应时间短，产率高，操作简便以及对环境友好。J.杂环化​​学，（2009）。
• Synthesis of 1,2,6,8-tetraazapyrenes by the reaction of aldehydes and ketones of 1H-perimidine series with diethyl azodicarboxylate in polyphosphoric acid
  作者：A. M. Zhirov、A. S. Kolesnikova、I. V. Aksenova、A. S. Lyakhovnenko、A. V. Aksenov

  DOI：10.1007/s11172-013-0153-7

  日期：2013.4

  on the reaction of 6(7) formyl(benzoyl)perimidines with diethyl azodicar boxylate. Lewis5—8 or Brønsted acids8,9 were used as catalysts in the reaction of azodicarboxylates with arenes. We showed that the reaction of 6(7) formyl(benzo yl)perimidines 1a—c with a two fold excess of diethyl azodicarboxylate (2) in polyphosphoric acid (PPA) at 80—90 C with subsequent treatment of the reaction mix ture

  氮杂芘用作荧光 DNA 嵌入剂 1，其中还发现了具有细胞毒性 2 和镇痛活性的化合物。 3 然而，目前已知的合成此类化合物的方法数量有限，1,2、 6,8 四氮杂芘仅在一项工作中进行了描述。4 在本工作中，我们提出了一种基于 6(7) 甲酰基（苯甲酰基）芘与二乙基苯反应合成 1,2,6,8 四氮杂芘的方法偶氮羧酸酯。Lewis5-8 或 Brønsted 酸 8,9 被用作偶氮二羧酸盐与芳烃反应的催化剂。我们证明了 6(7) 甲酰基 (苯甲酰基) 嘧啶 1a-c 与两倍过量的偶氮二羧酸二乙酯 (2) 在多磷酸 (PPA) 中的反应在 80-90 C 下进行，随后对反应混合物进行处理与水和形成的溶液回流产生 1,2,6,8 四氮杂芘 3a-c，产率为 32-37%（方案 1）。建议的这种转化机制（方案 2）包括偶氮化合物 2 与哌啶 1a-c 的迈克尔加成，产生肼 5，其环化形成四氮杂芘的二氢衍生物
• Novel approach to the synthesis of 1,3-diazapyrenes
  作者：A. V. Aksenov、I. V. Borovlev、I. V. Aksenova、D. A. Lobach、A. S. Lyakhovnenko

  DOI：10.1007/s10593-009-0227-5

  日期：2009.1

  Methods have been developed for the synthesis of 1,3-diazapyrenes based on the reactions of perimidines with ethoxymethylene-1,3-dicarbonyl compounds and also 6(7)-benzoyl(acetyl, formyl)perimidines with carbonyl compounds in PPA.
• Synthesis of N-Phenyl-1,5,7-Triazacyclopenta[cd]- Phenalenes by the Reaction of 1H-Perimidine Carbonyl Derivatives with Nitrobenzene
  作者：S. V. Shcherbakov、D. A. Lobach、M. Rubin、A. V. Aksenov

  DOI：10.1007/s10593-014-1531-2

  日期：2014.8
• 6(7)-Acylperimidines nitration and methods of peri-annelation on this base
  作者：A. V. Aksenov、N. A. Aksenov、A. S. Lyakhovnenko、A. N. Smirnov、I. I. Levina、I. V. Aksenova

  DOI：10.1007/s10593-013-1335-9

  日期：2013.10

  A method has been developed for the nitration of 6(7)-acylperimidines using sodium nitrite in formic acid. The reaction gives a mixture of 4(9)-, 9(4)-, and 7(6)-nitro-6(7)-acylperimidines from which the latter can be separated by extraction with chloroform. Reduction of the 6(7)-acyl-7(6)-nitro- perimidines yields 1H-1,5,7-triazacyclopenta[cd]phenalenes. Subsequent Schmidt reaction and reduction give 1,3,6,8-tetraazapyrenes.