(+/-)-acetylvasicinone | 72710-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+/-)-acetylvasicinone
• 英文别名: 9-oxo-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-yl acetate；3-acetoxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one；(9-oxo-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-3-yl) acetate
• CAS: 72710-66-8
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: OLUXFKYXVWAQOW-UHFFFAOYSA-N

物化性质

• 沸点：
  398.1±44.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-acetylvasicinone 在 sodium hydroxide 、 Lipase PS 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 7.25h， 生成 鸭嘴花碱酮
  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
• 作为产物：
  描述：

  2-叠氮苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 氯化亚砜 、 18-冠醚-6 、 三乙胺 、 sodium iodide 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 13.25h， 生成 (+/-)-acetylvasicinone
  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

• A Polymer-Assisted Solution-Phase Strategy for the Synthesis of Fused [2,1-<i>b</i>]Quinazolinones and the Preparation of Optically Active Vasicinone
  作者：Ahmed Kamal、V. Devaiah、N. Shankaraiah、K. Reddy

  DOI：10.1055/s-2006-951482

  日期：2006.9

  An efficient preparation of fused [2,1-b]quinazolinones has been developed utilizing polymer-supported reagents. (±)-Vasicinone was converted into its dione by oxidation with poly (4-vinylpyridiniumdichromate). An efficient method has been developed for the synthesis of (d)- and (l)-vasicinone via asymmetric reduction of pyrrolo[2,l-b]quinazoline-3,9-dione by employing NaBH 4 /Me 3 SiCl as the reducing

  利用聚合物支持的试剂开发了一种有效制备稠合 [2,1-b] 喹唑啉酮的方法。(±)-Vasicinone 通过用聚（4-乙烯基吡啶重铬酸盐）氧化转化为二酮。已经开发了一种通过使用 NaBH 4 /Me 3 SiCl 作为还原剂和 pyrrolo[2,lb]quinazoline-3,9-dione 的不对称还原来合成 (d)- 和 (l)-vasicinone 的有效方法。聚合物负载的手性磺酰胺作为催化剂。
• Toward new camptothecins. Part 5: On the synthesis of precursors for the crucial Friedländer reaction
  作者：Thomas Boisse、Laurent Gavara、Jean-Pierre Hénichart、Benoît Rigo、Philippe Gautret

  DOI：10.1016/j.tet.2009.01.077

  日期：2009.3

  The synthesis of potential precursors of ketones, which could be used to obtain camptothecin analogs, is described. Noteworthy is the difference of reactivity between indolizinone and pyrrolidinoquinazolinone heterocycle.

  描述了可用于获得喜树碱类似物的酮的潜在前体的合成。值得注意的是吲哚嗪酮和吡咯烷基喹唑啉酮杂环之间的反应性差异。
• Vasicol, a new alkaloid from Adhatoda vasica
  作者：K.L. Dhar、M.P. Jain、S.K. Koul、C.K. Atal

  DOI：10.1016/0031-9422(81)85115-1

  日期：1981.1

  Abstract A novel alkaloid isolated from the roots of Adhatoda vasica has been characterized as 1,2,3,4,9,11 hexahydro pyrrolo (2,1-b) quinazolin-3,11 diol by chemical and spectroscopic methods. Vasicinone has also been isolated from the roots of this plant.

  摘要 通过化学和光谱方法，从 Adhatoda vasica 根中分离出的一种新型生物碱已被表征为 1,2,3,4,9,11 六氢吡咯 (2,1-b) quinazolin-3,11 二醇。Vasicinone 也已从这种植物的根中分离出来。
• Nickel‐Catalyzed Intramolecular Dual Annulation Reaction of Alkyl Nitrile‐Containing 1,2,3‐Benzotriazin‐4(3H)‐ones: A Pathway to Access Diversely Polycyclic Quinazolinone Alkaloids
  作者：Vijaykumar H. Thorat、Yong‐Ran Huang、Hao‐Yu Chao、Jen‐Chieh Hsieh

  DOI：10.1002/adsc.202301512

  日期：2024.5.21

  Herein, we report a nickel‐catalyzed intramolecular dual annulation reaction of alkyl nitrile‐containing 1,2,3‐benzotriazine‐4(3H)‐ones to synthesize polycyclic quinazolinones. This catalytic reaction can construct the core structure of polycyclic quinazolinone alkaloids; therefore, we also apply this reaction as the critical step to access fifteen relevant alkaloids to demonstrate efficacy.

  在此，我们报道了含烷基腈的1,2,3-苯并三嗪-4(3H)-酮的镍催化分子内双环化反应来合成多环喹唑啉酮。该催化反应可以构建多环喹唑啉酮生物碱的核心结构；因此，我们也应用该反应作为获取十五种相关生物碱以证明功效的关键步骤。
• POI, (NEE CHAUDHURY) RAJLAKSHMI;ADITYACHAUDHURY, N., J. INDIAN CHEM. SOC., 65,(1988) N 11, C. 814
  作者：POI, (NEE CHAUDHURY) RAJLAKSHMI、ADITYACHAUDHURY, N.

  DOI：——

  日期：——