2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione | 50332-64-4

• 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: 2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione
• 英文别名: 5-ethyl-5H-[1,3]dioxolo[4',5':4,5]benzo[d][1,3]oxazine-6,8-dione；N-Ethyl-5,6-methylendioxyisatoinsaeureanhydrid；5-Ethyl-[1,3]dioxolo[4,5-g][3,1]benzoxazine-6,8-dione
• CAS: 50332-64-4
• 化学式: C₁₁H₉NO₅
• 分子量: 235.196
• InChiKey: ZLCCUHAGLQJRCH-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C(Solv: tetrahydrofuran (109-99-9))
• 沸点：
  411.8±55.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione 在 盐酸 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：

  4,5-methylenedioxyanthranilic acid hydrochloride 在 sodium hydride 作用下， 反应 2.5h， 生成 2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione
  参考文献：
  名称：

  喹诺酮-3-羧酸和腈的2,4-二取代衍生物的合成

  摘要：

  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。

  DOI：

  10.1002/jhet.5570240622

文献信息

• Albrecht,R., Chimica Therapeutica, 1973, vol. 8, p. 45 - 48
  作者：Albrecht,R.

  DOI：——

  日期：——
• 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：——
• MITSCHER L. A.; GRACEY H. E.; CLARK G. W.; SUZUKI T., J. MED. CHEM., 1978, 21, NO 5, 485-489
  作者：MITSCHER L. A.、 GRACEY H. E.、 CLARK G. W.、 SUZUKI T.

  DOI：——

  日期：——
• Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
  作者：L. A. Mitscher、H. E. Gracey、G. W. Clark、T. Suzuki

  DOI：10.1021/jm00203a018

  日期：1978.5

  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.
• 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。