6-(2-Azidophenyl)-5,8-dimethylisoquinoline | 109855-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(2-Azidophenyl)-5,8-dimethylisoquinoline
• CAS: 109855-81-4
• 化学式: C₁₇H₁₄N₄
• 分子量: 274.325
• InChiKey: ZEYBINXLDCLIRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-Azidophenyl)-5,8-dimethylisoquinoline 以 均三甲苯 为溶剂， 反应 5.0h， 以63%的产率得到isoellipticine
  参考文献：
  名称：

  Preparation of Polyfunctional Aryl Azides from Aryl Triazenes. A New Synthesis of Ellipticine, 9-Methoxyellipticine, Isoellipticine, and 7-Carbethoxyisoellipticine

  摘要：

  [GRAPHICS]The preparation of polyfunctional aryl azides by the reaction of aryl triazenes with NaN3 in the presence of KHSO4 or BF3 center dot OEt2/TFA (trifluoroacetic acid) has been described. A variety of functional groups (halides, esters, ketones, nitriles, aldehydes, and boronic esters) are tolerated under the Lewis acidic conditions. By using this methodology, the potent antitumor agents, ellipticine and 9-methoxyellipticine, have been synthesized. In addition, isoellipticine and a related derivative, 7-carbethoxyisoellipticine, were also prepared.

  DOI：

  10.1021/jo070774z
• 作为产物：
  描述：

  N,N-tetramethylene-N'-(2'-iodophenyl)triazene 在 potassium hydrogensulfate 、 lithium chloro-isopropyl-magnesium chloride 、 sodium azide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 6-(2-Azidophenyl)-5,8-dimethylisoquinoline
  参考文献：
  名称：

  Preparation of Polyfunctional Aryl Azides from Aryl Triazenes. A New Synthesis of Ellipticine, 9-Methoxyellipticine, Isoellipticine, and 7-Carbethoxyisoellipticine

  摘要：

  [GRAPHICS]The preparation of polyfunctional aryl azides by the reaction of aryl triazenes with NaN3 in the presence of KHSO4 or BF3 center dot OEt2/TFA (trifluoroacetic acid) has been described. A variety of functional groups (halides, esters, ketones, nitriles, aldehydes, and boronic esters) are tolerated under the Lewis acidic conditions. By using this methodology, the potent antitumor agents, ellipticine and 9-methoxyellipticine, have been synthesized. In addition, isoellipticine and a related derivative, 7-carbethoxyisoellipticine, were also prepared.

  DOI：

  10.1021/jo070774z

文献信息

• Miller, R. Bryan; Dugar, Sundeep; Epperson, James R., Heterocycles, 1987, vol. 25, p. 217 - 220
  作者：Miller, R. Bryan、Dugar, Sundeep、Epperson, James R.

  DOI：——

  日期：——
• BRYAN, MILLER R.;DUGA, S.;EPPERSON, J. R., HETEROCYCLES, 25,(1987) NPEC. ISSUE, 217-220
  作者：BRYAN, MILLER R.、DUGA, S.、EPPERSON, J. R.

  DOI：——

  日期：——
• Preparation of Polyfunctional Aryl Azides from Aryl Triazenes. A New Synthesis of Ellipticine, 9-Methoxyellipticine, Isoellipticine, and 7-Carbethoxyisoellipticine
  作者：Ching-Yuan Liu、Paul Knochel

  DOI：10.1021/jo070774z

  日期：2007.9.1

  [GRAPHICS]The preparation of polyfunctional aryl azides by the reaction of aryl triazenes with NaN3 in the presence of KHSO4 or BF3 center dot OEt2/TFA (trifluoroacetic acid) has been described. A variety of functional groups (halides, esters, ketones, nitriles, aldehydes, and boronic esters) are tolerated under the Lewis acidic conditions. By using this methodology, the potent antitumor agents, ellipticine and 9-methoxyellipticine, have been synthesized. In addition, isoellipticine and a related derivative, 7-carbethoxyisoellipticine, were also prepared.