2-Methyl-10H-benzo-1,8-naphthyrid-5-one | 28907-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-Methyl-10H-benzo-1,8-naphthyrid-5-one
• 英文别名: 2-methylbenzo[b][1,8]naphthyridin-5(10H)-one；2-methylbenzo[b][1,8]naphtyridin-5(10H)-one；2-methyl-10H-benzo[b][1,8]naphthyridin-5-one
• CAS: 28907-37-1
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: WPEAAPGEKNRNBA-UHFFFAOYSA-N

物化性质

• 熔点：
  278-279 °C
• 沸点：
  391.0±31.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-anilino-6-methyl-nicotinic acid 在 PPA 作用下， 反应 5.0h， 以50%的产率得到2-Methyl-10H-benzo-1,8-naphthyrid-5-one
  参考文献：
  名称：

  Reactions of 6-methyl- and 4,6-dimethyl-2-arylaminonicotinonitriles with acids

  摘要：

  DOI：

  10.1007/bf00526089

文献信息

• Synthesis of Pyrido-Fused Quinazolinone Derivatives via Copper-Catalyzed Domino Reaction
  作者：Meilin Liu、Miaomiao Shu、Chaochao Yao、Guodong Yin、Dunjia Wang、Jinkun Huang

  DOI：10.1021/acs.orglett.6b00113

  日期：2016.2.19

  simple and efficient synthesis of 11H-pyrido[2,1-b]quinazolin-11-ones by Cu(OAc)2·H2O-catalyzed reaction of easily available substituted isatins and 2-bromopyridine derivatives has been developed. The reaction involves C–N/C–C bond cleavage and two C–N bond formations in a one-pot operation. This methodology is complementary to previously reported synthetic procedures, and two plausible reaction mechanisms

  通过Cu（OAc）2 ·H 2 O催化易得的取代的靛红与2-溴吡啶衍生物的反应，可以简单，有效地合成11 H-吡啶并[ 2,1 - b ]喹唑啉-11-酮。该反应在一锅操作中涉及C–N / CC键断裂和两个C–N键形成。该方法是对先前报道的合成方法的补充，并讨论了两个合理的反应机理。
• Synthesis of 9‐Methyl‐11H‐pyrido[2,1‐b]quinazolin‐11‐one Using the Ullmann Condensation
  作者：Rolando F. Pellón、Maite L. Docampo、Zulfia Kunakbaeva、Victoria Gómez、Herman Vélez‐Castro

  DOI：10.1080/00397910500384566

  日期：2006.3.1

  Abstract The Ullmann condensation between 2‐chlorobenzoic acid and 2‐amino‐6‐methyl pyridine in DMF as solvent yielded 2‐[(6‐methyl‐2‐pyridinyl)amino] benzoic acid. The cyclization of this acid gave two isomers, the 9‐methyl‐11H‐pyrido[2,1‐b]quinazolin‐11‐one and, in a minor quantity, 2‐methylbenzo[b][1,8]naphtyridin‐5(10H)‐one. Using ultrasound irradiation the pyridoquinazolin‐11‐one was obtained

  摘要 2-氯苯甲酸与 2-氨基-6-甲基吡啶在 DMF 溶剂中进行乌尔曼缩合反应生成 2-[(6-甲基-2-吡啶基)氨基]苯甲酸。该酸的环化得到两种异构体，9-甲基-11H-吡啶并[2,1-b]喹唑啉-11-one和少量的2-甲基苯并[b][1,8]萘啶-5 (10H)-一个。使用超声辐照获得吡啶并喹唑啉-11-one 作为唯一产品​​。
• Research on naphthyridines. 11. Synthesis and ionization constants of substituted 10H-benzo[b]-1,8-naphthyrid-5-ones
  作者：N. I. Shramm、M. E. Konshin

  DOI：10.1007/bf00515644

  日期：1984.3
• Ni(0) catalyzed one step synthesis of benzo[b][1,8] naphthyridin-5-ones from silyl-α-ketoalkynes in water
  作者：Gloria Alejandra Suárez-Ortiz、Pankaj Sharma、Manuel Amézquita-Valencia、Ivonne Arellano、A. Cabrera、Noé Rosas

  DOI：10.1016/j.tetlet.2011.01.123

  日期：2011.4

  One-step synthesis of new benzo[b][1,8]naphthyridin-5-ones using a Ni(0) catalytic system in aqueous medium with mild conditions of pressure and temperature is described. It is very interesting to note that Ni(0) catalyst increases the rate of condensation of several alpha-ketoalkynes with 2-amino-4(1H)-quinolinone obtaining benzo[b][1,8]naphthyridin-5-ones in very high yield. In the absence of catalyst this condensation reaction takes 24 h with a product yield of < 10%. (C) 2011 Elsevier Ltd. All rights reserved.
• SHRAMM, N. I.;KONSHIN, M., XIMIYA GETEROTSIKL. SOEDIN., 1982, N 5, 674-678
  作者：SHRAMM, N. I.、KONSHIN, M.

  DOI：——

  日期：——