1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione | 57385-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione
• 英文别名: 2H-6,7-methylenedioxy-3,1-benzoxazine-2,4(1H)-dione；3,4-(methylenedioxy)isatoic anhydride；5,6-Methylendioxyisatoinsaeureanhydrid；5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d][1,3]oxazine-6,8-dione；5H-[1,3]dioxolo[4,5-g][3,1]benzoxazine-6,8-dione
• CAS: 57385-14-5
• 化学式: C₉H₅NO₅
• 分子量: 207.142
• InChiKey: WVYVUUTZEICIND-UHFFFAOYSA-N

物化性质

• 熔点：
  258-259 °C(Solv: tetrahydrofuran (109-99-9))
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione 在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 恶喹酸
  参考文献：
  名称：

  Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

  摘要：

  A flexible reaction sequence has been developed which starts with readily available anthranilic acids or isatoic anhydrides and leads regiospecifically to 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids after reaction with 1,3-dicarbonyl compounds. The sequence is superior to earlier published methods by allowing electron-releasing and -withdrawing groups in any position on the aro;atic ring, by allowing convenient substitution at C2, and better overall yield. A number of new and known antimicrobial agents were prepared and tested in vitro, demonstrating, inter alia, that substitution of the H at C2 abolished antibacterial activity.

  DOI：

  10.1021/jm00203a018
• 作为产物：
  描述：

  6--1,3-benzodioxole-5-carboxylic acid 在 乙酰氯 作用下， 反应 2.0h， 以58%的产率得到1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione
  参考文献：
  名称：

  Gakhar, H. K.; Kaur, Rajinder; Raheja, Simmi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 1, p. 48 - 50

  摘要：

  DOI：

文献信息

• The chemistry of 2<i>H</i>-3,1-benzoxazine-2,4(1<i>H</i>)dione (isatoic anhydrides) 1. The synthesis of<i>N</i>-substituted 2<i>H</i>-3,1-benzoxazine-2,4(1<i>H</i>)diones
  作者：Goetz E. Hardtmann、Gabor Koletar、Oskar R. Pfister

  DOI：10.1002/jhet.5570120325

  日期：1975.6

  Three methods for the preparation of N-substituted 2H-3,1-benzoxazine-2,4(1H)diones (isatoic anhydrides) (1) utilizing 2-chloro-, 2-nitrobenzoic acids and N-unsubstituted isatoic anhydrides as starting materials, are described.

  三种制备N-取代的2 H -3,1-苯并恶嗪-2,4（1 H）二酮（乙酸酐）的方法（1）使用2-氯-，2-硝基苯甲酸和N-未取代的等角酸酐作为制备方法描述了起始材料。
• The synthesis of some 2,4-disubstituted derivatives of quinolone-3-carboxylic acids and carbonitriles
  作者：D. L. Leysen、A. Haemers、W. Bollaert、R. A. Dommisse、E. L. Esmans

  DOI：10.1002/jhet.5570240622

  日期：1987.11

  the 2-chloro derivative of oxolinic acid, ethyl 1-ethyl-1,4-dihydro-2-hydroxy-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylate was treated with phosphorus oxychloride. The compound obtained was the 4-chloro-2-oxo-quinoline. The structure was confirmed by 13C nmr and mass spectral techniques. The 2-halocarbonitrile was obtained by a Sandmeyer reaction but could not be hydrolysed into the acid.

  为了制备草酸的2-氯衍生物，用氯氧化磷处理1-乙基-1，4-二氢-2-羟基-6，7-亚甲基二氧基-4-氧代-3-喹啉羧酸乙酯。得到的化合物是4-氯-2-氧代-喹啉。通过13 C nmr和质谱技术证实了该结构。通过桑德迈尔反应获得了2-卤代腈，但是不能被水解成酸。
• Nickel-Catalyzed Intramolecular Dual Annulation Reaction of Aryl Nitrile-Containing 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Pathway To Synthesize Luotonin A and Related Polycyclic Pyrroloquinazolinones
  作者：Vijaykumar H. Thorat、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.3c03142

  日期：2023.11.10

  Herein, we report a nickel-catalyzed intramolecular denitrogenative dual annulation reaction of aryl nitrile-containing 1,2,3-benzotriazine-4(3H)-ones to synthesize polycyclic pyrroloquinazolinones with a tolerance of a wide diversity of substituents. This catalytic reaction is the first denitrogenative transannulation of 1,2,3-benzotriazine-4(3H)-one with nitrile, which can be applied as the critical

  在此，我们报道了含芳基腈的1,2,3-苯并三嗪-4(3 H )-酮的镍催化分子内脱氮双环化反应，合成了具有多种取代基的多环吡咯并喹唑啉酮。该催化反应是1,2,3-苯并三嗪-4(3H)-酮与腈的首次脱氮转环反应，可作为合成洛托宁A的关键步骤，具有较高的步骤经济性。
• Studies of rutaecarpine and related quinazolinocarboline alkaloids
  作者：Jan Bergman、Solveig Bergman

  DOI：10.1021/jo00208a018

  日期：1985.4
• LEYSEN, D. L.;HAEMERS, A.;BOLLAERT, W.;DOMMISSE, R. A.;ESMANS, E. L., J. HETEROCYCL. CHEM., 24,(1987) N 6, 1611-1616
  作者：LEYSEN, D. L.、HAEMERS, A.、BOLLAERT, W.、DOMMISSE, R. A.、ESMANS, E. L.

  DOI：——

  日期：——