7-bromo-5,8-dimethylisoquinoline | 952303-59-2

• 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-bromo-5,8-dimethylisoquinoline
• CAS: 952303-59-2
• 化学式: C₁₁H₁₀BrN
• 分子量: 236.111
• InChiKey: WFKQFFYLYJTSIS-UHFFFAOYSA-N

物化性质

• 熔点：
  102.5-103.5 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  332.8±37.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-5,8-dimethylisoquinoline 在 lithium chloro-isopropyl-magnesium chloride 、 sodium azide 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 均三甲苯 为溶剂， 反应 12.25h， 生成 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：

  5-bromo-4,7-dimethyl-1H-indene 在 ammonium hydroxide 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 7-bromo-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。
• Synthesis of 7-Substituted Derivatives of 5,8-Dimethylisoquinoline
  作者：Yukinori Nagao、Katsuaki Hirota、Mizuho Tokumaru、Kozo Kozawa

  DOI：10.3987/com-07-s(u)38

  日期：——

  7-Bromo-5,8-dimethylisoquinoline was selectively synthesized by the bromination of 5,8-dimethylisoquinoline obtained in five steps from p-xylene as a starting material. Further, 7-bromo-5,8-dimethylisoquinoline gave 7-amino-5,8-dimethylisoquinoline by the reaction with ammonia and various 7-anilino-5,8-dimethylisoquinolines via a palladium-catalyzed coupling reaction with anilines.
• Synthesis of 7-Anilino-5,8-dimethylisoquinolines Having Electron-Attracting Group on Anilino Moiety
  作者：Yukinori Nagao、Ryosuke Endo、Mizuho Tokumaru、Koji Arimitsu

  DOI：10.3987/com-08-s(f)110

  日期：——

  7-Amino-5,8-dimethylisoquinoline gave various 7-anilino-5,8-dimethylisoquinolines via a palladium-catalyzed coupling reaction with bromobenzenes having electron-attracting groups (NO(2), F).