(噌啉-3-基)(呋喃-2-基)甲酮 | 337512-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: (噌啉-3-基)(呋喃-2-基)甲酮
• 英文名称: (cinnolin-3-yl)(furan-2-yl)methanone
• 英文别名: 3-(2-furoyl)-cinnoline；3-(2-furoyl)cinnoline；Cinnolin-3-yl(furan-2-yl)methanone
• CAS: 337512-21-7
• 化学式: C₁₃H₈N₂O₂
• 分子量: 224.219
• InChiKey: OAENFVXACSHZRG-UHFFFAOYSA-N

物化性质

• 沸点：
  430.6±43.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (噌啉-3-基)(呋喃-2-基)甲酮 900.0 ℃ 、2.67 Pa 条件下， 反应 -6.0h， 以80%的产率得到二苯并呋喃
  参考文献：
  名称：

  Flash vacuum pyrolysis of 3-aroylcinnolines: interesting routes toward polynuclear aromatic compounds

  摘要：

  Flash vacuum pyrolysis of 3-aroylcinnolines 3 at 900 degreesC and 0.02 Torr yielded phenanthrene and arylacetylene derivatives as the major products beside anthracene, and diarylacetylene derivatives as minor products. Also, FVP of 3-(2-thienoyl)-cinnoline gave three isomeric naphthothiophenes, phenyl-2-thienylacetylene and phenylacetylene. On the other hand, 3-(2-furoyl)-cinoline gave dibenzofuran as a major product besides naphtho[1,2-b]furan and phenylacetylene. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00577-4
• 作为产物：
  描述：

  3-(2-furyl)-3-oxo-2-(phenylhydrazono)propanal 以 乙腈 为溶剂， 反应 0.17h， 生成 (噌啉-3-基)(呋喃-2-基)甲酮
  参考文献：
  名称：

  有机合成中的气相热解。第 3 部分：将 2-芳基肼基丙醛环化为 cinnolines1

  摘要：

  3-oxo-3-aryl-2-arylhydrazonopropanals (1) 已在热气相条件下干净地转化为 cinnolines (2)。基于动力学和反应产物，提出了一种合理的机制来解释这种转变。© 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 402–406, 2001

  DOI：

  10.1002/kin.1035

文献信息

• Efficient synthesis of 3-aroylcinnolines from aryl methyl ketones
  作者：Nouria A Al-Awadi、Mohamed Hilmy Elnagdi、Yehia A Ibrahim、Kamini Kaul、Ajith Kumar

  DOI：10.1016/s0040-4020(00)01141-8

  日期：2001.2

  An efficient synthesis of 3-aroylcinnolines starting from the appropriate aryl methyl ketones is described. The latter were converted in two steps to the corresponding 3-oxo-3-aryl-2-arylhydrazonopropanals, which upon acid catalyzed cyclization in conc. sulfuric acid or polyphosphoric acid (PPA) led to the corresponding 3-aroylcinnolines.

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。
• Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study
  作者：Shanghui Tian、Yunyun Liu、Changfeng Wan、Jie-Ping Wan、Guifeng Hao

  DOI：10.1021/acs.joc.2c02858

  日期：2023.2.17

  A simple and concise method for the synthesis of cinnolines has been developed by the reactions of readily available enaminones and aryl diazonium tetrafluoroboronates. The reactions run efficiently to provide cinnolines with broad diversity in the substructure by heating in dimethyl sulfoxide without using any catalyst or additive. In addition, the primary investigation of the anti-inflammatory activity

  通过容易获得的烯胺酮和芳基四氟硼酸重氮盐的反应，开发了一种简单明了的合成肉啉的方法。在不使用任何催化剂或添加剂的情况下，通过在二甲亚砜中加热，反应可以高效运行，从而提供亚结构具有广泛多样性的肉啉。此外，对这些产品的抗炎活性的初步研究导致观察到对氯苯甲酰 ( 3f ) 和对硝基苯甲酰 ( 3j ) 肉啉作为有吸引力的体外抗炎化合物。
• TMP–Magnesium and TMP–Zinc Bases for the Regioselective Metalation of the Cinnoline Scaffold
  作者：Thomas Klatt、Daniela Sustac Roman、Thierry León、Paul Knochel

  DOI：10.1021/ol5001999

  日期：2014.2.21

  A regioselective functionalization of cinnolines in positions 3 and 8 using metalations has been developed. This involves either the use of a frustrated Lewis pair consisting of BF3 center dot Et2O and TMP2Mg center dot 2LiCl or the in situ generated base TMP2Zn center dot 2MgCl(2)center dot 2LiCl. Successive metalations allow the preparation of 3,8-disubstituted cinnolines. Various functionalizations by acylation, allylation, and cross-coupling reactions with aryl halides or alkenyl iodides were carried out successfully.
• Flash vacuum pyrolysis of 3-aroylcinnolines: interesting routes toward polynuclear aromatic compounds
  作者：Yehia A Ibrahim、Nouria A Al-Awadi、Kamini Kaul

  DOI：10.1016/s0040-4020(01)00577-4

  日期：2001.8

  Flash vacuum pyrolysis of 3-aroylcinnolines 3 at 900 degreesC and 0.02 Torr yielded phenanthrene and arylacetylene derivatives as the major products beside anthracene, and diarylacetylene derivatives as minor products. Also, FVP of 3-(2-thienoyl)-cinnoline gave three isomeric naphthothiophenes, phenyl-2-thienylacetylene and phenylacetylene. On the other hand, 3-(2-furoyl)-cinoline gave dibenzofuran as a major product besides naphtho[1,2-b]furan and phenylacetylene. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Gas-phase pyrolysis in organic synthesis. Part 3: Novel cyclization of 2-arylhydrazonopropanals into cinnolines1
  作者：Ajith Kumar、Nouria A. Al-Awadi、Mohamed H. Elnagdi、Yehia A. Ibrahim、Kamini Kaul

  DOI：10.1002/kin.1035

  日期：2001.7

  3-oxo-3-aryl-2-arylhydrazonopropanals (1) have been converted under thermal gas-phase conditions cleanly into cinnolines (2). A plausible mechanism is suggested to account for this transformation based on the kinetics and products of reaction. © 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 402–406, 2001

  3-oxo-3-aryl-2-arylhydrazonopropanals (1) 已在热气相条件下干净地转化为 cinnolines (2)。基于动力学和反应产物，提出了一种合理的机制来解释这种转变。© 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 402–406, 2001