5,17-bis(bromoacetylamino)-25,26,27,28-tetrapropoxycalix[4]arene | 560116-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,17-bis(bromoacetylamino)-25,26,27,28-tetrapropoxycalix[4]arene
• CAS: 560116-40-7
• 化学式: C₄₄H₅₂Br₂N₂O₆
• 分子量: 864.715
• InChiKey: GGTBENBUUQVLGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.19
• 重原子数：
  54.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  95.12
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  腺嘌呤 、 5,17-bis(bromoacetylamino)-25,26,27,28-tetrapropoxycalix[4]arene 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以27.4%的产率得到2-(6-aminopurin-9-yl)-N-[17-[[2-(6-aminopurin-9-yl)acetyl]amino]-25,26,27,28-tetrapropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]acetamide
  参考文献：
  名称：

  Synthesis of new calix[4]arenes containing nucleoside bases

  摘要：

  A family of novel calix[4]arene derivatives containing nucleoside bases were designed and synthesized. Coupling reaction between para mono- or bis-amino calix[4]arenes 5,6 or 7 and thymin-1-ylacetic acid in the presence of DCC afforded mono- or bis-thymine-substituted calix[4]arenes 8, 9 or 10 in over 70% yield. Owing to the low solubility of adenine-N-9-ylacetic acid in DMF and DMSO and the weak nucleophilicity of aminocalix[4]arene derivatives, alternatively, the substitution reaction of bromoacetylated ammocalix[4]arenes derivatives 11, 12, 13 with adenine in the presence of sodium hydride was carried out to synthesize mono- or bis-adenine-substituted calix[4]arenes. Two kinds of isomers 15 and 16 or 17 and 18 were obtained due to the non-regiospecific alkylation of adenine, and their structures have been confirmed by C-13 NMR and H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00251-5
• 作为产物：
  描述：

  5,17-dinitro-25,26,27,28-tetrapropoxycalix[4]arene 在 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 5,17-bis(bromoacetylamino)-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  Synthesis of new calix[4]arenes containing nucleoside bases

  摘要：

  A family of novel calix[4]arene derivatives containing nucleoside bases were designed and synthesized. Coupling reaction between para mono- or bis-amino calix[4]arenes 5,6 or 7 and thymin-1-ylacetic acid in the presence of DCC afforded mono- or bis-thymine-substituted calix[4]arenes 8, 9 or 10 in over 70% yield. Owing to the low solubility of adenine-N-9-ylacetic acid in DMF and DMSO and the weak nucleophilicity of aminocalix[4]arene derivatives, alternatively, the substitution reaction of bromoacetylated ammocalix[4]arenes derivatives 11, 12, 13 with adenine in the presence of sodium hydride was carried out to synthesize mono- or bis-adenine-substituted calix[4]arenes. Two kinds of isomers 15 and 16 or 17 and 18 were obtained due to the non-regiospecific alkylation of adenine, and their structures have been confirmed by C-13 NMR and H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00251-5