(9ci)-2,3-二氢-2-氧代-1H-氮杂卓-3-羧酸 | 134050-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 中文名称: (9ci)-2,3-二氢-2-氧代-1H-氮杂卓-3-羧酸
• 英文名称: 3H-azepin-2-one-3-carboxylic acid
• 英文别名: 2-oxo-(3H)-azepine-3-carboxylic acid；1H-Azepine-3-carboxylicacid,2,3-dihydro-2-oxo-(9CI)；2-oxo-1,3-dihydroazepine-3-carboxylic acid
• CAS: 134050-77-4
• 化学式: C₇H₇NO₃
• mdl: MFCD18807241
• 分子量: 153.137
• InChiKey: LPBQMXBUEVTMJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-叠氮苯甲酸 在 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以50%的产率得到(9ci)-2,3-二氢-2-氧代-1H-氮杂卓-3-羧酸
  参考文献：
  名称：

  通过2-叠氮基苯甲酸的碱介导的光化学NO键形成环化反应合成2,1-苯并恶唑-3（1H）-酮。

  摘要：

  据报道，碱介导的2-叠氮苯甲酸的光化学环化与2,1-苯并恶唑-3（1H）-的形成。讨论了该环化反应的优化和范围。结果表明2-叠氮基苯甲酸闭环的关键步骤是2-叠氮基苯甲酸根阴离子的形成和光解。

  DOI：

  10.3762/bjoc.12.86

文献信息

• Continuous flow photolysis of aryl azides: Preparation of 3<i>H</i>-azepinones
  作者：Farhan R Bou-Hamdan、François Lévesque、Alexander G O'Brien、Peter H Seeberger

  DOI：10.3762/bjoc.7.129

  日期：——

  Photolysis of aryl azides to give nitrenes, and their subsequent rearrangement in the presence of water to give 3H-azepinones, is performed in continuous flow in a photoreactor constructed of fluorinated ethylene polymer (FEP) tubing. Fine tuning of the reaction conditions using the flow reactor allowed minimization of secondary photochemical reactions.

  芳基叠氮化物的光解产生亚硝基，然后在水存在下发生重排反应生成3H-氮杂七酮，这一过程在由氟化乙烯聚合物（FEP）管构建的光反应器中连续进行。利用流动反应器对反应条件进行微调，可以最小化次级光化学反应。
• Synthesis of 2,1-benzisoxazole-3(1<i>H</i>)-ones by base-mediated photochemical N–O bond-forming cyclization of 2-azidobenzoic acids
  作者：Daria Yu Dzhons、Andrei V Budruev

  DOI：10.3762/bjoc.12.86

  日期：——

  The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.

  据报道，碱介导的2-叠氮苯甲酸的光化学环化与2,1-苯并恶唑-3（1H）-的形成。讨论了该环化反应的优化和范围。结果表明2-叠氮基苯甲酸闭环的关键步骤是2-叠氮基苯甲酸根阴离子的形成和光解。
• 3H-azepines and related systems. Part 4. Preparation of 3H-azepin-2-ones and 6H-azepino[2,1-b]quinazolin-12-ones by photo-induced ring expansions of aryl azides
  作者：Kaddour Lamara、Robert K. Smalley

  DOI：10.1016/s0040-4020(01)96138-1

  日期：——

  Photolysis of a series of p-substituted phenyl azides (p-X-C6H4N3; X = CO2Me, CO2Et, CN, CF3, SO2NH2, CO2CHPh2, COMe, CHO, and NO2) in 1:1 (nu/nu) THF-water solution produces, in the majority of cases, a 5-substituted-3H-azepine-2-one. In a like manner, 3H-azepin-2-one-3-carboxylates can be prepared from 5-substituted-2-azidobenzoates, providing the 5-substituent is electron-withdrawing.3H-Azepin-2-one mono- and di-carboxylic acids, the former in admixture with decarboxylated material, and 6H-azepino[2,1-b]quinazolin-12-ones, are obtained by irradiation of 2-azidobenzoic acid and of 5-azidoisophthalic acid, respectively. The mode of formation of the azepino-quinazolinones is discussed.
• Effect of water on product yields of 2-azidobenzoic acid photolysis in aprotic solvents
  作者：D. Yu. Sinjagina、A. V. Budruev

  DOI：10.1134/s0018143913040127

  日期：2013.7

  The effect of water admixtures on the formation of 2-oxo-(3H)-azepine-3-carboxylic acid and 2,1-benzisoxazol-3(1H)-one in the photolysis of 2-azidobenzoic acid in aprotic solvents has been investigated. It has been shown that the addition of nucleophilic agents to the reaction mixture determines the yields of not only 3H-azepines, the products of benzene ring expansion, but also the intramolecular cyclization product 2,1-benzisoxazol-3(1H)-one. Participation of the formed 2,1-benzisoxazol-3(1H)-one in the reaction has been suggested as an explanation of the effect of nucleophilic compounds (water, ethanol, and 2,1-benzisoxazol-3(1H)-one) on the product yield of the monomolecular reaction.
• Effect of an External Heavy Atom on the Product Yield of Photoinduced Heterocyclization of 2-Azidobenzoic Acid
  作者：A. V. Budruev、M. A. Giricheva、D. A. Davydov、A. V. Pokrovskaia、A. L. Pronina

  DOI：10.1134/s0018143921060047

  日期：2021.11