3-butylamino-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione | 501335-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-butylamino-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione
• 英文别名: 3-(Butylamino)-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7-dione
• CAS: 501335-26-8
• 化学式: C₁₂H₁₇N₅O₂
• 分子量: 263.299
• InChiKey: VUTXQJIIIJQKLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-butylamino-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione 在 manganese(IV) oxide 、 bis(pyridine)silver(I) permanganate 作用下， 以 苯 为溶剂， 反应 168192.0h， 生成 2,4,11,13-tetramethyl-7-propyl-8-butyl-7,8-dihydrobenzo[1",2":4,5;4",3":4',5']bis(pyrrolo[2,3-c]pyrimido[5,4-e]pyridazine)-1,3,12,14(2H,4H,11H,13H)-tetraone
  参考文献：
  名称：

  6,8-Dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione: new heterocyclizations based on SNH-methodology. Unexpected formation of the first iso-π-electronic analogue of the still unknown dibenzo[a,o]pycene

  摘要：

  N-(2)-Oxide and 3-amino derivatives of 6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione have been shown to react with primary alkylamines in the presence of an oxidant to produce condensed imidazolines or imidazoles. Both conversions based on S-N(H)-strategy represent a new approach to imidazoline-(imidazole-)ring annulation. Heterocyclic analogues of the still unknown dibenzo[a,o]pycene were obtained as a by-products of the above transformations upon using of cyclohexylamine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.002
• 作为产物：
  描述：

  3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione 、 正丁胺 在 AgPy₂MNo₄ 作用下， 反应 24.0h， 以60%的产率得到4-butylamino-3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione
  参考文献：
  名称：

  嘌呤、嘧啶和相关的融合系统。21. 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione 的氧化胺化

  摘要：

  3-氯-6,8-二甲基嘧啶并[4,5-c]哒嗪-5,7(6H,8H)-二酮与伯烷基胺和氨化钾在液氨中的氧化胺化产生相应的4-氨基衍生物，如主要产品。与无环仲胺的反应伴随着吡咯部分与起始杂系统的退火形成 1-R-3-R"-6,8-二甲基吡咯并[2",3";3,4]嘧啶[4,5 -c]pyridazine-7,9(6H,8H)-diones。与作为胺化剂的哌啶的反应仅以氨基脱卤的形式发生。4-氨基-3-氯-6,8-二甲基嘧啶[4]的 Sonogashira 交叉偶联,5-c]哒嗪-5,7(6H,8H)-二酮与末端炔烃提供 1-R-2-R"-6,8-二甲基吡咯并[3",2";3,4]嘧啶[4, 5-c]哒嗪-7,9(6H,8H)-二酮。

  DOI：

  10.1023/b:rucb.0000037854.46887.7f

文献信息

• Cycloalkano[1″,2″:4,5;4″,3″:4′,5′]bis(pyrrolo[2,3-c]pyrimido[5,4-e]pyridazines): synthesis, structure and mechanism of their formation
  作者：Olga V. Serduke、Anna V. Gulevskaya、Alexander F. Pozharskii、Zoya A. Starikova、Irina A. Profatilova

  DOI：10.1016/j.tet.2005.10.008

  日期：2006.1

  Reactions of 3-alkylamino-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones with cyclohexyl- and cycloheptylamines in the presence of AgPy2MnO4 produce novel cycloalkano[1″,2″:4,5;4″,3″:4′,5′]bis(pyrrolo[2,3-c]pyrimido[5,4-e]pyridazines). Detailed information concerning the scope and mechanism of these transformations is discussed.

  在AgPy 2 MnO 4存在下，3-烷基氨基-6,8-二甲基嘧啶[4,5- c ]哒嗪-5,7（6 H，8 H）-二酮与环己基和环庚胺的反应产生了新型环烷[1] ”，2”：4,5; 4”，3”：4'，5'] bis（pyrrolo [2,3- c ] pyrimido [5,4- e ] pyridazines）。讨论了有关这些转换的范围和机制的详细信息。
• Pyrimido[4,5-<i>c</i>]pyridazine-5,7(6<i>H</i>, 8<i>H</i>)-diones: Marvelous substrates for study of nucleophilic substitution of hydrogen
  作者：Alexander F. Pozharskii、Anna V. Gulevskaya

  DOI：10.1002/jhet.5570420304

  日期：2005.4

  The data on nucleophilic substitution reactions of hydrogen in 6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione, its 3-chloride, N2-oxide and some other derivatives are reviewed. All these compounds possess a remarkable ability to undergo not only simple functionalizations but also tandem and cascade transformations leading to annelation of various heterocyclic rings.

  氢在6,8-二甲基嘧啶[4,5- c ]哒嗪-5,7（6 H，8 H）-二酮，其3-氯化物，N 2-氧化物和一些其他衍生物中的亲核取代反应数据如下：已审查。所有这些化合物都具有显着的能力，不仅能够进行简单的官能化，而且还能进行串联和级联转化，从而导致各种杂环的环化。
• 6,8-Dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione: a novel approach to imidazoline (imidazole) ring annulation based on the methodology
  作者：Anna V. Gulevskaya、Alexander F. Pozharskii、Denis V. Besedin、Olga V. Serduke、Zoya A. Starikova

  DOI：10.1070/mc2002v012n04abeh001624

  日期：2002.1

  The N-(2)-oxide and 3-amino derivatives of the title compound react with alkylamines in the presence of an oxidant,to produce condensed imidazolines or their imidazole analogues.