7-氧代-6,7-二氢-1H-氮杂卓-4-羧酸 | 134050-71-8

• 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: 7-氧代-6,7-二氢-1H-氮杂卓-4-羧酸
• 中文别名: 1H-氮杂卓-4-羧酸,6,7-二氢-7-羰基-(9CI)
• 英文名称: 3H-azepin-2-one-5-carboxylic acid
• 英文别名: 2-Oxo-1,3-dihydroazepine-5-carboxylic acid
• CAS: 134050-71-8
• 化学式: C₇H₇NO₃
• mdl: MFCD18807246
• 分子量: 153.137
• InChiKey: LBJSLLUCTQNCJY-UHFFFAOYSA-N

物化性质

• 沸点：
  434.5±45.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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

• 作为反应物：
  描述：

  7-氧代-6,7-二氢-1H-氮杂卓-4-羧酸 、 二苯基重氮甲烷 以 四氢呋喃 为溶剂， 以88%的产率得到diphenylmethyl 3H-azepin-2-one-5-carboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)96138-1
• 作为产物：
  描述：

  对叠氮苯甲酸 以 四氢呋喃 、 水 为溶剂， 反应 19.0h， 以36%的产率得到7-氧代-6,7-二氢-1H-氮杂卓-4-羧酸
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)96138-1

文献信息

• Skeletal Editing of Benzene Motif: Photopromoted Transannulation for Synthesis of DNA-Encoded Seven-Membered Rings
  作者：Yue Zhang、Jia-ying Xue、Xiao-can Su、Wen-jie Xiao、Jing-yi Lv、Wen-xia Shi、Yong Zou、Ming Yan、Xue-jing Zhang

  DOI：10.1021/acs.orglett.4c00377

  日期：2024.3.22

  photopromoted, metal-free transannulation of phenyl azides for the synthesis of DNA-encoded seven-membered rings. The transformation is efficiently achieved through a skeletal editing strategy targeting the benzene motif coupled with a Reversible Adsorption to Solid Support (RASS) strategy. A variety of valuable DNA-encoded seven-membered ring compounds, including DNA-encoded 3H-azepines, azepinones, and

  在本报告中，我们提出了一种光促进、无金属的苯基叠氮化物转环反应，用于合成 DNA 编码的七元环。该转化是通过针对苯基序的骨架编辑策略与可逆吸附到固体支持物（RASS）策略相结合而有效实现的。现在可以获得多种有价值的 DNA 编码的七元环化合物，包括 DNA 编码的 3H-氮杂卓、氮杂酮和非天然氨基酸。至关重要的是，这种与 DNA 兼容的方案也可用于引入复杂分子，例如 Lorcaserin 和 Betahistine。将容易获得的苯环选择性地转化为高价值的七元环，为构建多样化和类药物的 DNA 编码库提供了一条有前途的途径。
• 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.