2-methyl-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one | 60811-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-methyl-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one
• 英文别名: 2-methyl-6,7,8,9-tetrahydro-pyrido[2,1-b]quinazolin-11-one
• CAS: 60811-44-1
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: WLRUBXKNIWJVPH-UHFFFAOYSA-N

物化性质

• 熔点：
  90 °C
• 沸点：
  387.0±35.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one 、 丁香醛 反应 0.2h， 生成 6-[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-2-methyl-6,7,8,9-tetrahydro-pyrido[2,1-b]quinazolin-11-one
  参考文献：
  名称：

  Privileged structure-based quinazolinone natural product-templated libraries: Identification of novel tubulin polymerization inhibitors

  摘要：

  A focused quinazolinone natural product-templated library was designed and synthesized. Compounds from this privileged structure-based library were identified as antimitotic agents acting through destabilization of tubulin polymerization. The results suggested that 2 could be a privileged substructure. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.022
• 作为产物：
  描述：

  2-azido-5-methyl-benzoyl chloride 在 三甲基氯硅烷 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.25h， 生成 2-methyl-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Pyrrolo[2,1-b]quinazolinones:  Lipase-Catalyzed Resolution of Vasicinone

  摘要：

  A facile synthesis of bronchodilatory pyrrolo [2,1-b] quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.

  DOI：

  10.1021/jo0011484

文献信息

• Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones
  作者：Ahmed Kamal、K.Venkata Ramana、Hari Babu Ankati、A.Venkata Ramana

  DOI：10.1016/s0040-4039(02)01454-5

  日期：2002.9

  FeCl3/NaI has been employed for an efficient reduction of a variety of azides. This method is selective in the presence of a nitro functionality and has been extended for the synthesis of fused [2,1-b]quinazolinone ring systems such as deoxyvasicinone.

  FeCl 3 / NaI已用于有效还原各种叠氮化物。该方法在硝基官能团存在的情况下是选择性的，并且已经扩展为合成稠合的[ 2,1- b ]喹唑啉酮环系统，例如脱氧维辛酮。
• One-Pot Synthesis of Simple Alkaloids: 2,3-Polymethylene-4(3<i>H</i>)-quinazolinones, Luotonin A, Tryptanthrin, and Rutaecarpine
  作者：Katherine Chae Jahng、Seung Ill Kim、Dong Hyeon Kim、Chang Seob Seo、Jong-Keun Son、Seung Ho Lee、Eung Seok Lee、Yurngdong Jahng

  DOI：10.1248/cpb.56.607

  日期：——

  One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl2 is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

  本文描述了从邻氨基苯甲酸、相应的内酰胺和SOCl2中一锅合成多种2,3-聚甲基-4(3H)-喹唑啉酮的方法，该方法可用于合成简单的4(3H)-喹唑啉酮衍生物生物碱，如鲁托霉素A、曲普坦和鲁托卡品。
• 10.1039/d4ob00529e
  作者：Zhang, Yuanmu、Zhu, Lingxuan、Lu, Yi、Lei, Xinsheng、Li, Yingxia

  DOI：10.1039/d4ob00529e

  日期：——

  skeletons occupy a prominent position in drug discovery. Even with currently available methods there still remain unmet needs for flexible access to such structures. Herein, we have explored a mild “one pot” procedure for the construction of various quinazolinone-[2,3]-fused polycycles. The procedure involves Pd-catalyzed carbonylation of N-(2-iodophenyl)acetamides, release of the masked terminal amine

  多种喹唑啉酮-[2,3]-稠合多环骨架在药物发现中占据着重要地位。即使采用当前可用的方法，对于灵活访问此类结构的需求仍然未得到满足。在此，我们探索了一种温和的“一锅法”程序来构建各种喹唑啉酮-[2,3]-稠合多环。该过程包括 Pd 催化的N- (2-碘苯基)乙酰胺的羰基化、掩蔽末端胺的释放以及两个连续的自发环化。这种普遍适用的方法具有从容易获得的起始材料中轻松组装前体、反应条件温和、操作不繁琐和多环多样性的特点。
• Chemoenzymatic Synthesis of Pyrrolo[2,1-<i>b</i>]quinazolinones:  Lipase-Catalyzed Resolution of Vasicinone
  作者：Ahmed Kamal、K. Venkata Ramana、Maddamsetty V. Rao

  DOI：10.1021/jo0011484

  日期：2001.2.1

  A facile synthesis of bronchodilatory pyrrolo [2,1-b] quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.
• Privileged structure-based quinazolinone natural product-templated libraries: Identification of novel tubulin polymerization inhibitors
  作者：Ji-Feng Liu、Christopher J. Wilson、Ping Ye、Kevin Sprague、Katie Sargent、Ying Si、Galina Beletsky、Daniel Yohannes、Shi-Chung Ng

  DOI：10.1016/j.bmcl.2005.10.022

  日期：2006.2

  A focused quinazolinone natural product-templated library was designed and synthesized. Compounds from this privileged structure-based library were identified as antimitotic agents acting through destabilization of tubulin polymerization. The results suggested that 2 could be a privileged substructure. (c) 2005 Elsevier Ltd. All rights reserved.