N-<3'-(benzyloxy)-6'-bromo-2'-methoxybenzyl>-6,7-(methylenedioxy)-1-naphthylamine | 95712-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<3'-(benzyloxy)-6'-bromo-2'-methoxybenzyl>-6,7-(methylenedioxy)-1-naphthylamine
• 英文别名: N-(6-bromo-2-methoxy-3-(benzyloxy)benzyl)-6,7-(methylenedioxy)-1-naphthylamine；N-[(6-bromo-2-methoxy-3-phenylmethoxyphenyl)methyl]benzo[f][1,3]benzodioxol-5-amine
• CAS: 95712-58-6
• 化学式: C₂₆H₂₂BrNO₄
• 分子量: 492.369
• InChiKey: QLUNLMIJEBSWSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  616.6±50.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-<3'-(benzyloxy)-6'-bromo-2'-methoxybenzyl>-6,7-(methylenedioxy)-1-naphthylamine 在 盐酸 、 氨 、 potassium amide 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 德卡林碱
  参考文献：
  名称：

  Benzyne cyclization route to benzo[c]phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine

  摘要：

  DOI：

  10.1021/jo00243a020
• 作为产物：
  描述：

  3-羟基-2-甲氧苯甲醛 在 dimethylamine borane 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 N-<3'-(benzyloxy)-6'-bromo-2'-methoxybenzyl>-6,7-(methylenedioxy)-1-naphthylamine
  参考文献：
  名称：

  Revision of the Structure of Fagaridine Based on the Comparison of UV and NMR Data of Synthetic Compounds

  摘要：

  Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2,3-(methylenedioxy)-benzo[c]phenanthridinium (1). We have synthesized this compound, coded NK109, aiming at a practical antitumor drug, and during synthetic studies we questioned the original assigned structure. Thus, we synthesized 8-hydroxy-7-methoxy-5-methyl-2,3-(methylenedioxy)benzo[c]phenanthridinium (2), isomer of the assigned structure, and compared the spectroscopic data of both 1 and 2. The NMR data of 1 and 2 were very similar, but the UV spectra were completely different. The UV data for fagaridine agreed with these for 2; consequently, the true structure of fagaridine is 2, not 1.

  DOI：

  10.1021/np980193s

文献信息

• Kessar, Satinder Vir; Gupta, Yash Pal; Mohammad, Taj, Heterocycles, 1984, vol. 22, # 12, p. 2723 - 2724
  作者：Kessar, Satinder Vir、Gupta, Yash Pal、Mohammad, Taj、Khurana, Achla、Sawal, Kewal Krishan

  DOI：——

  日期：——
• KESSAR, SATINDER V.;GUPTA, YASH P.;BALAKRISHNAN, PRASANNA;SAWAL, KEWAL K.+, J. ORG. CHEM., 53,(1988) N 8, 1708-1713
  作者：KESSAR, SATINDER V.、GUPTA, YASH P.、BALAKRISHNAN, PRASANNA、SAWAL, KEWAL K.+

  DOI：——

  日期：——
• Benzyne cyclization route to benzo[c]phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine
  作者：Satinder V. Kessar、Yash P. Gupta、Prasanna Balakrishnan、Kewal K. Sawal、Taj Mohammad、Mahesh Dutt

  DOI：10.1021/jo00243a020

  日期：1988.4
• Revision of the Structure of Fagaridine Based on the Comparison of UV and NMR Data of Synthetic Compounds
  作者：Takeshi Nakanishi、Masanobu Suzuki

  DOI：10.1021/np980193s

  日期：1998.10.1

  Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2,3-(methylenedioxy)-benzo[c]phenanthridinium (1). We have synthesized this compound, coded NK109, aiming at a practical antitumor drug, and during synthetic studies we questioned the original assigned structure. Thus, we synthesized 8-hydroxy-7-methoxy-5-methyl-2,3-(methylenedioxy)benzo[c]phenanthridinium (2), isomer of the assigned structure, and compared the spectroscopic data of both 1 and 2. The NMR data of 1 and 2 were very similar, but the UV spectra were completely different. The UV data for fagaridine agreed with these for 2; consequently, the true structure of fagaridine is 2, not 1.