7-(2-azidophenyl)-5,8-dimethylisoquinoline | 109855-79-0

• 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: 7-(2-azidophenyl)-5,8-dimethylisoquinoline
• CAS: 109855-79-0
• 化学式: C₁₇H₁₄N₄
• 分子量: 274.325
• InChiKey: BEWZDBJNCNFPMK-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：

  7-(2-azidophenyl)-5,8-dimethylisoquinoline 以 均三甲苯 为溶剂， 反应 6.0h， 以57%的产率得到椭圆玫瑰树碱
  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：

  在 sodium azide 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到7-(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

• Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine
  作者：Tibor Soós、Dániel Horváth、Frigyes Domonyi、Roberta Palkó、Andrea Lomoschitz

  DOI：10.1055/s-0037-1609153

  日期：2018.6

  functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products. A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This

  摘要 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。
• 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：——