3-chloro-4-cyano-10-ethoxycarbonylmethylthio-5,10-dihydrobenzo[b][1,6]naphthyridine | 383895-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-chloro-4-cyano-10-ethoxycarbonylmethylthio-5,10-dihydrobenzo[b][1,6]naphthyridine
• 英文别名: Ethyl [(3-chloro-4-cyano-5,10-dihydrobenzo[b][1,6]naphthyridin-10-yl)sulfanyl]acetate；ethyl 2-[(3-chloro-4-cyano-5,10-dihydrobenzo[b][1,6]naphthyridin-10-yl)sulfanyl]acetate
• CAS: 383895-85-0
• 化学式: C₁₇H₁₄ClN₃O₂S
• 分子量: 359.836
• InChiKey: UWHCBCCXQULVSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-chloro-4-cyano-10-ethoxycarbonylmethylthio-5,10-dihydrobenzo[b][1,6]naphthyridine 在 sodium acetate 作用下， 以 异丙醇 为溶剂， 反应 4.5h， 以61%的产率得到4-cyano-3-ethoxycarbonylmethylthiobenzo[b][1,6]naphthyridine
  参考文献：
  名称：

  摘要：

  The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable sigma-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting sigma-complexes are rearranged into sulfides 14a-c. Sulfides 14b,c undergo the Thorpe-Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of sigma-adducts of the C-N and C-C types, while those with aliphatic amines yield 3-amino derivatives 17a-c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.

  DOI：

  10.1023/a:1021636632164
• 作为产物：
  描述：

  1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine 在 水 、 溶剂黄146 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 3-chloro-4-cyano-10-ethoxycarbonylmethylthio-5,10-dihydrobenzo[b][1,6]naphthyridine
  参考文献：
  名称：

  摘要：

  The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable sigma-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting sigma-complexes are rearranged into sulfides 14a-c. Sulfides 14b,c undergo the Thorpe-Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of sigma-adducts of the C-N and C-C types, while those with aliphatic amines yield 3-amino derivatives 17a-c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.

  DOI：

  10.1023/a:1021636632164