1-cinnamyl-1H-benzo[d][1,3]oxazine-2,4-dione | 57385-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1-cinnamyl-1H-benzo[d][1,3]oxazine-2,4-dione
• 英文别名: 1-Cinnamyl-2H-3,1-benzoxazin-2,4(1H)-dion；1-(3-phenyl-allyl)-1H-benzo[d][1,3]oxazine-2,4-dione；1-Cinnamyl-1h-benzo[d][1,3]oxazine-2,4-dione；1-(3-phenylprop-2-enyl)-3,1-benzoxazine-2,4-dione
• CAS: 57385-02-1
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: XCVKKAGBRUWWQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-cinnamylindoline-2,3-dione 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以89%的产率得到1-cinnamyl-1H-benzo[d][1,3]oxazine-2,4-dione
  参考文献：
  名称：

  Chemoselective oxidation of 1-alkenylisatins with m-chloroperbenzoic acid. Synthesis of new derivatives of isatoic anhydride

  摘要：

  Oxidation of alkyl- and alkenylisatins with m-chloroperbenzoic acid proceeds with high chemoselectivity leading to the formation of 1-substituted isatoic anhydrides (benzo[d][1,3]oxazine-2,4-diones) without epoxidation of the double bond of the alkenyl substituent. This result is in accordance with the data of DFT quantum chemical calculations using the B3LYP functional in conjunction with the basis set of atomic orbitals 6-31G(d,p). The structure of the synthesized heterocyclic compounds was proved by NMR and X-ray diffraction data.

  DOI：

  10.1134/s1070363215090030

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。
• Chemoselective oxidation of 1-alkenylisatins with m-chloroperbenzoic acid. Synthesis of new derivatives of isatoic anhydride
  作者：A. V. Bogdanov、T. I. Sadykov、L. I. Musin、A. R. Khamatgalimov、D. B. Krivolapov、A. B. Dobrynin、V. F. Mironov

  DOI：10.1134/s1070363215090030

  日期：2015.9

  Oxidation of alkyl- and alkenylisatins with m-chloroperbenzoic acid proceeds with high chemoselectivity leading to the formation of 1-substituted isatoic anhydrides (benzo[d][1,3]oxazine-2,4-diones) without epoxidation of the double bond of the alkenyl substituent. This result is in accordance with the data of DFT quantum chemical calculations using the B3LYP functional in conjunction with the basis set of atomic orbitals 6-31G(d,p). The structure of the synthesized heterocyclic compounds was proved by NMR and X-ray diffraction data.