1,3-dimethyl-6-(3-methoxyphenyl)uracil | 105202-44-6

• 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: 1,3-dimethyl-6-(3-methoxyphenyl)uracil
• 英文别名: 1,3-dimethyl-6-(meta-methoxyphenyl)uracil；1,3-dimethyl-6-(m-methoxyphenyl)uracil；6-(3-Methoxyphenyl)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 105202-44-6
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: CAKATNZYVWIONW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 、 3-碘苯甲醚 在 copper(I) bromide 、 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以72%的产率得到1,3-dimethyl-6-(3-methoxyphenyl)uracil
  参考文献：
  名称：

  Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C–H bond activation

  摘要：

  A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.001

文献信息

• Pd(II)-catalyzed regioselective direct arylation of uracil via oxidative Heck reaction using arylboronic acids
  作者：Biplab Mondal、Somjit Hazra、B. Roy

  DOI：10.1016/j.tetlet.2013.12.092

  日期：2014.1

  A palladium catalyzed regioselective synthesis of 6-aryl uracils via oxidative Heck reaction (C–H bond functionalization) of uracils and arylboronic acids is reported. The method is simple, atom-economical, and high yielding.

  据报道，钯通过尿嘧啶和芳基硼酸的氧化Heck反应（CH键功能化）催化6-芳基尿嘧啶的区域选择性合成。该方法简单，原子经济且产率高。
• Palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil with aryl bromides: an electrophilic metalation–deprotonation with electrophilic arylpalladium intermediate
  作者：Ko Hoon Kim、Hyun Seung Lee、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.09.066

  日期：2011.11

  An efficient method of palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil was developed with a various range of aryl bromides including electron-deficient aryl bromides. 5-Aryluracil derivatives were obtained in moderate to good yields regioselectively most likely via an electrophilic metalation–deprotonation process.

  开发了一种有效的钯催化的1,3-二甲基尿嘧啶的直接5-芳基化反应，该方法使用了各种范围的芳基溴化物，包括缺电子的芳基溴化物。5-芳基尿嘧啶衍生物是通过亲电金属化-去质子化过程以区域选择性高至中等收率获得的。
• Photolysis of 5-bromo-1,3-dimethyluracil in substituted benzenes.
  作者：KOH-ICHI SEKI、KOHKI MATSUDA、YUKO BANDO、KAZUE OHKURA

  DOI：10.1248/cpb.36.4737

  日期：——

  Photolysis of5-bromo-1, 3-dimethyluracil (5-BDMU) in substituted benzenes afforded the corresponding 5-aryl derivatives together with the unexpected 6-isomers as an isomeric mixture. The 6-isomers were found to be derived from the protonated 5-BDMU, presumably via the interaction between LUMO5-BDMU (in the excited triplet state) and LUMOaryl (in the ground state).

  光解取代苯中的 5-溴-1, 3-二甲基尿嘧啶（5-BDMU）可得到相应的 5-芳基衍生物以及意想不到的 6-异构体异构体混合物。研究发现，6-异构体来自质子化的 5-BDMU，可能是通过 LUMO5-BDMU（激发三重态）和 LUMOaryl（基态）之间的相互作用产生的。
• Synthesis of Cyclooctapyrimidine-2,4-diones by Photocycloadition of 6-Chloro-1,3-dimethyluracil to Benzenes in the Presence of Trifluoroacetic Acid.
  作者：Kazue OHKURA、Nobuhiko KANAZASHI、Koh-ichi SEKI

  DOI：10.1248/cpb.41.239

  日期：——

  Photoreaction of 6-chloro-1, 3-dimethyluracil in benzene and monosubstituted benzenes furnished cycloaddition products, cyclooctapyrimidine-2, 4-dione derivatives, in the presence of trifluoroacetic acid.

  在三氟乙酸存在下，6-氯-1, 3-二甲基尿嘧啶在苯和单取代苯中的光反应产生了环加成产物，即环辛基嘧啶-2, 4-二酮衍生物。
• PHOTOLYSIS OF 5-BR0M0-1,3-DIMETHYLURACIL IN SUBSTITUTED BENZENES
  作者：Koh-ichi Seki、Yuko Bando、Kazue Ohkura

  DOI：10.1246/cl.1986.195

  日期：1986.2.5

  Photolysis of 5-bromo-1,3-dimethyluracil in toluene, xylene and anisole afforded the anormalously substituted 6-aryl-1,3-dimethyluracils beside the expected products 5-aryl-1,3-dimethyluracils, while the reaction with veratrole occurred exclusively at the 5-position of the uracil ring.

  5-溴-1,3-二甲基尿嘧啶在甲苯、二甲苯和苯甲醚中的光解得到6-芳基-1,3-二甲基尿嘧啶和预期产物5-芳基-1,3-二甲基尿嘧啶，同时与藜芦发生反应仅在尿嘧啶环的 5 位。