1-(3'-methyl-2'-butenyl)-3-diazoquinoline-2,4-dione | 223668-14-2

• 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: 1-(3'-methyl-2'-butenyl)-3-diazoquinoline-2,4-dione
• 英文别名: 3-Diazonio-1-(3-methylbut-2-enyl)-4-oxoquinolin-2-olate
• CAS: 223668-14-2
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: AXISBWXMGSRAFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3'-methyl-2'-butenyl)-3-diazoquinoline-2,4-dione 在 copper(I) bromide 作用下， 以 水 、 苯甲腈 为溶剂， 反应 4.0h， 以86%的产率得到1-(3-methylbut-2-en-1-yl)indoline-2,3-dione
  参考文献：
  名称：

  通过3-重氮 喹啉-2,4-二酮的环收缩合成各种isatins †

  摘要：

  通过铜介导的多米诺夫·沃尔夫重排，脱羧，溴化，取代和脱水，通过环介导的3-重氮喹啉-2,4-二酮的铜介导反应，完成了各种靛红衍生物的有效合成。该协议作为一锅法具有几个优点，具有官能团耐受性和高收率。

  DOI：

  10.1039/c6ra13585d
• 作为产物：
  描述：

  1-(3'-methyl-2'-butenyl)isatoic anhydride 在 sodium hydride 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1-(3'-methyl-2'-butenyl)-3-diazoquinoline-2,4-dione
  参考文献：
  名称：

  Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones

  摘要：

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.

  DOI：

  10.1021/jo982503h

文献信息

• One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(<scp>iii</scp>)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor
  作者：Rajeev Shrestha、Hari Datta Khanal、Yong Rok Lee

  DOI：10.1039/c9ra03146d

  日期：——

  efficient Rh(III)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinediones is described. Furthermore, the methodology is applicable for delivering various relevant molecules such as pyridopyranoquinolindiones, thienopyranoquinolinones, and indolopyranoquinolinone. The reaction proceeds via cascade C–H activation, carbene

  描述了一种简便高效的 Rh( III ) 催化芳基酰胺与 3-重氮喹啉二酮的环化，用于构建多种高度功能化的异色烯喹啉二酮。此外，该方法适用于传递各种相关分子，如吡喃并吡喃喹啉二酮、噻吩并吡喃喹啉酮和吲哚吡喃喹啉酮。该反应通过级联 C-H 活化、卡宾插入和分子内内酯化进行。该反应具有高原子经济性、良好的官能团耐受性和高区域选择性。合成的化合物还可以作为 Fe 3+离子的有效荧光传感器。
• Synthesis of diverse isatins via ring contraction of 3-diazoquinoline-2,4-diones
  作者：Rajeev Shrestha、Gun Joon Lee、Yong Rok Lee

  DOI：10.1039/c6ra13585d

  日期：——

  An efficient synthesis of diverse isatin derivatives was accomplished by a copper-mediated reaction of 3-diazoquinoline-2,4-diones via ring contraction through domino Wolff rearrangement, decarboxylation, bromination, substitution, and dehydration. This protocol has several advantages as a one-pot procedure, with functional group tolerance, and high yield.

  通过铜介导的多米诺夫·沃尔夫重排，脱羧，溴化，取代和脱水，通过环介导的3-重氮喹啉-2,4-二酮的铜介导反应，完成了各种靛红衍生物的有效合成。该协议作为一锅法具有几个优点，具有官能团耐受性和高收率。
• Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones
  作者：Michael C. Pirrung、Florian Blume

  DOI：10.1021/jo982503h

  日期：1999.5.1

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.