8-bromo-[1,3]dioxolo[4,5-g]quinoline | 35478-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-bromo-[1,3]dioxolo[4,5-g]quinoline
• 英文别名: 4-Brom-6,7-methylendioxychinolin；4-Bromo-6,7-methylenedioxyquinoline
• CAS: 35478-80-9
• 化学式: C₁₀H₆BrNO₂
• 分子量: 252.067
• InChiKey: OCIBTGYHEKBKLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-bromo-[1,3]dioxolo[4,5-g]quinoline 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 6,7-methylenedioxy-4-quinolyllithium
  参考文献：
  名称：

  Process for piperidine intermediates for quinine, quinidine and analogs

  摘要：

  奎宁、奎尼丁及其类似物是通过将4-喹诺啉锂化合物与4,5-赤露-5-乙基（或乙烯基）喹啉-2.ε-羧醛或相应的喹啉-2-羧酸烷基酯反应制备而成。此外，还描述了4,5-赤露-5-乙基（或乙烯基）喹啉-2.ε-羧醛以及4,5-赤露-5-乙基（或乙烯基）喹啉-2.ε-羧酸及其酯的制备方法。最终产品可用作抗疟疾和抗心律失常药物。

  公开号：

  US03931192A1
• 作为产物：
  描述：

  6,7-methylenedioxy-4-quinolone 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以46%的产率得到8-bromo-[1,3]dioxolo[4,5-g]quinoline
  参考文献：
  名称：

  Assembly of 4-Aminoquinolines via Palladium Catalysis:  A Mild and Convenient Alternative to S_NAr Methodology

  摘要：

  4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)(2)/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.

  DOI：

  10.1021/jo062168u

文献信息

• Quinuclidine derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US03931193A1

  公开（公告）日：1976-01-06

  Quinine, quinidine and analogs thereof, are prepared by reacting a 4-quinolyllithium compound with a 4,5-erythro-5-ethyl(or vinyl)-quinuclidine-2 .xi.-carboxaldehyde or the corresponding quinuclidine-2-carboxylic acid alkyl ester. Also described, inter alia, is the preparation of a 4,5-erythro-5-ethyl(or vinyl)-quinuclidine-2 .xi.-carboxaldehyde, and a 4,5-erythro-5-ethyl(or vinyl)-quinuclidine-2 .xi.-carboxylic acid and esters thereof. The end products are useful as anti-malarial and antiarrhythmic agents.

  喹啉、奎宁和其类似物是通过将4-喹啉基锂化合物与4,5-红酒糟-5-乙基（或乙烯基）喹诺啉-2-羧醛或相应的喹诺啉-2-羧酸烷基酯反应制备的。此外，还描述了制备4,5-红酒糟-5-乙基（或乙烯基）喹诺啉-2-羧醛、4,5-红酒糟-5-乙基（或乙烯基）喹诺啉-2-羧酸及其酯的方法。最终产品可用作抗疟疾和抗心律失常药物。
• Brook Rearrangement as Trigger for Dearomatization Reaction: Synthesis of Non‐Aromatic <i>N</i>‐Heterocycles**
  作者：Rajarshi Mondal、Mohamed Agbaria、Orit Cohen、Zackaria Nairoukh

  DOI：10.1002/chem.202303588

  日期：2024.1.11

  [1,2]-Brook rearrangement can dearomatize aromatic N-heterocycles! Through a one-pot four-step process that includes lithiation, nucleophilic addition, Brook rearrangement, and dearomatization reaction, we enable the formation of non-aromatic N-heterocycles with functional capabilities starting from readily available precursors. Subsequent functionalization reactions provide access to a diverse compound

  [1,2]-布鲁克重排可以使芳香族N-杂环脱芳构化！通过包括锂化、亲核加成、Brook重排和脱芳构化反应的一锅四步工艺，我们能够从容易获得的前体开始形成具有功能性的非芳香族N-杂环。随后的功能化反应提供了对不同化合物库的访问。
• 11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents
  作者：Wei Feng、Mavurapu Satyanarayana、Yuan-Chin Tsai、Angela A. Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/j.bmc.2008.08.018

  日期：2008.9

  Several 11-substituted benzo[i]phenanthridine derivatives were synthesized, and their TOP1-targeting activity and cytotoxicity were assessed. Comparative data indicate that TOP1-targeting was often the primary molecular target associated with their cytotoxicity. Several 11-aminoalkyl derivatives, 11-aminocarboxy derivatives as well as the 11-[(2-dimethylamino)ethyl]carboxamide of 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine were synthesized and did exhibit considerable cytotoxicity with IC50 values ranging from 20 to 120 nM in the human lymphoblast tumor cell line RPMI8402. (C) 2008 Elsevier Ltd. All rights reserved.
• US3931192A
  申请人：——

  公开号：US3931192A

  公开（公告）日：1976-01-06
• US3931193A
  申请人：——

  公开号：US3931193A

  公开（公告）日：1976-01-06