5-amido-6-(3'-methoxylphenyl)-8-benzyloxy-9-methoxy-1,2-dihydrobenzo[d]azocin-4-one | 1415026-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5-amido-6-(3'-methoxylphenyl)-8-benzyloxy-9-methoxy-1,2-dihydrobenzo[d]azocin-4-one
• CAS: 1415026-83-3
• 化学式: C₃₃H₃₀N₂O₅
• 分子量: 534.612
• InChiKey: SQJWEBJWHHHDCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-amido-6-(3'-methoxylphenyl)-8-benzyloxy-9-methoxy-1,2-dihydrobenzo[d]azocin-4-one 在 palladium(II) trifluoroacetate 、 氧气 、 copper diacetate 、 sodium hydroxide 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 20.08h， 以53%的产率得到(2-Benzyloxyl-3,12-dimethoxyl)-5,6,7,9-tetrahydroindolo[2,3-e][3]benzazocin-8-one
  参考文献：
  名称：

  Palladium-catalyzed intramolecular C–H amidation: synthesis and biological activities of indolobenzazocin-8-ones

  摘要：

  The synthesis of multi ring-fused indolobenzazocinone derivatives, an antimitotic agent, has been carried out using palladium-catalyzed C-H activation/intramolecular amidation of benzo[d]azocinones, which were synthesized by the ring annulations of dihydroisoquinolines and azlactone in refluxing acetonitrile. The target compounds, indolobenzazocin-8-one derivatives, were evaluated for their cytotoxicity against the cancer cell lines HUCCA-1, A549, HepG2, and MOLT-3. The results showed that an unsubstituted indolobenzazocin-8-one le exhibited very good activities in the nanomolar IC50 value range (HepG2 and MOLT-3). Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.011
• 作为产物：
  描述：

  3-甲氧基苯甲酸 以 乙腈 为溶剂， 生成 5-amido-6-(3'-methoxylphenyl)-8-benzyloxy-9-methoxy-1,2-dihydrobenzo[d]azocin-4-one
  参考文献：
  名称：

  Palladium-catalyzed intramolecular C–H amidation: synthesis and biological activities of indolobenzazocin-8-ones

  摘要：

  The synthesis of multi ring-fused indolobenzazocinone derivatives, an antimitotic agent, has been carried out using palladium-catalyzed C-H activation/intramolecular amidation of benzo[d]azocinones, which were synthesized by the ring annulations of dihydroisoquinolines and azlactone in refluxing acetonitrile. The target compounds, indolobenzazocin-8-one derivatives, were evaluated for their cytotoxicity against the cancer cell lines HUCCA-1, A549, HepG2, and MOLT-3. The results showed that an unsubstituted indolobenzazocin-8-one le exhibited very good activities in the nanomolar IC50 value range (HepG2 and MOLT-3). Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.011