4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)isoxazole | 320591-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)isoxazole
• 英文别名: [(2R,3R,4R,5R)-5-[4-[(2-amino-5-nitrophenyl)iminomethyl]-1,2-oxazol-5-yl]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 320591-44-4
• 化学式: C₃₆H₂₈N₄O₁₀
• 分子量: 676.639
• InChiKey: USUNXFUGXWXLMM-WPXCQFTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)isoxazole 在 三氟乙酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以49%的产率得到3-cyano-8-nitro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-1,5-benzodiazepine
  参考文献：
  名称：

  Novel ring transformation of 5-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)isoxazole-4-carbaldehyde with 1,2-diaminobenzenes to 3-cyano-1,5-benzodiazepine C-nucleosides

  摘要：

  Syntheses of 3-cyano-7- and 8-substituted-4-(beta -D-ribofuranosyl)-1H-1,5-benzodiazepines were reported. Treatment of isoxazole carbaldehyde with 1,2-diamino-4-nitrobenzene in chloroform gave a Schiffs base, 4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl)isoxazole in 82% yield with no trace of the other regioisomer. The cyclocondensation of the resulting Schiffs base in benzene containing trifluoroacetic acid (TFA) gave 3-cyano-8-nitro-4-(2,3,5-tri-O-benzoyl-beta -D-rbofuranosyl)-1H-1,5-benzodiazepine in 49% yield. The same reac tion of isoxazole carbaldeyde with 1,2-diamino-4-methoxy- and 4-chlorobenzenes afforded the corresponding Schiffs bases. Extending the reaction time for Schiff's base gave the corresponding cyanobenzodiazepines in good yields. Debenzoylation of the compounds with sodium methoxide produced deprotected C-nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00231-7
• 作为产物：
  描述：

  4-硝基邻苯二胺 、 5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isoxazole-4-carbaldehyde 以 氯仿 为溶剂， 反应 120.0h， 以82%的产率得到4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)isoxazole
  参考文献：
  名称：

  Novel ring transformation of 5-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)isoxazole-4-carbaldehyde with 1,2-diaminobenzenes to 3-cyano-1,5-benzodiazepine C-nucleosides

  摘要：

  Syntheses of 3-cyano-7- and 8-substituted-4-(beta -D-ribofuranosyl)-1H-1,5-benzodiazepines were reported. Treatment of isoxazole carbaldehyde with 1,2-diamino-4-nitrobenzene in chloroform gave a Schiffs base, 4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl)isoxazole in 82% yield with no trace of the other regioisomer. The cyclocondensation of the resulting Schiffs base in benzene containing trifluoroacetic acid (TFA) gave 3-cyano-8-nitro-4-(2,3,5-tri-O-benzoyl-beta -D-rbofuranosyl)-1H-1,5-benzodiazepine in 49% yield. The same reac tion of isoxazole carbaldeyde with 1,2-diamino-4-methoxy- and 4-chlorobenzenes afforded the corresponding Schiffs bases. Extending the reaction time for Schiff's base gave the corresponding cyanobenzodiazepines in good yields. Debenzoylation of the compounds with sodium methoxide produced deprotected C-nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00231-7