6-bromo-1,3-dimethylperimidone | 162658-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-bromo-1,3-dimethylperimidone
• 英文别名: 6-bromo-1,3-dimethyl-1H-perimidin-2(3H)-one；6-bromo-1,3-dimethylperimidin-2-one
• CAS: 162658-22-2
• 化学式: C₁₃H₁₁BrN₂O
• 分子量: 291.147
• InChiKey: GDGORMIVWUVYNY-UHFFFAOYSA-N

物化性质

• 沸点：
  414.9±24.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)
• 溶解度：
  <0.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-1,3-dimethylperimidone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以95%的产率得到6-bromo-1,3-dimethyl-2,3-dihydroperimidine
  参考文献：
  名称：

  Vistorobskii, N. V.; Pozharskii, A. F., Russian Journal of Organic Chemistry, 1995, vol. 31, # 7, p. 997 - 1001

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-dimethyl-1H-perimidin-2(3H)-one 在 溴 作用下， 以 溶剂黄146 为溶剂， 以78%的产率得到6-bromo-1,3-dimethylperimidone
  参考文献：
  名称：

  Pozharskii, A.F.; Vistorobskii, N.V.; Grigoryan, V.S., Russian Journal of Organic Chemistry, 1994, vol. 30, # 6.2, p. 985 - 991

  摘要：

  DOI：

文献信息

• 1,3-Dipolar cycloaddition of azinium ylides to alkynyl hetarenes: a synthetic route to indolizine and pyrrolo[2,1-a]isoquinoline based heterobiaryls
  作者：Julia I. Nelina-Nemtseva、Anna V. Gulevskaya、Alexander F. Pozharskii、Huong T.L. Nguyen、Ekaterina A. Filatova

  DOI：10.1016/j.tet.2016.03.050

  日期：2016.5

  For the first time, π-deficient alkynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with in situ generated azinium ylides. A three-component reaction of pyridine or isoquinoline, ethyl chloroacetate and alkynyl hetarene (pyrazine, quinoxaline, uracil, or lumazine derivative) in the presence of a base gave the corresponding indolizine or pyrrolo[2,1-a]isoquinoline based

  第一次，在与原位生成的叠氮化物的1，3-偶极环加成反应中，将π缺乏的炔基戊烯用作亲极性。在碱存在下，吡啶或异喹啉，氯乙酸乙酯和炔基戊烯（吡嗪，喹喔啉，尿嘧啶或lumazine衍生物）的三组分反应得到相应的吲哚利嗪或吡咯并[2,1- a ]异喹啉基杂联芳基产量。反应以高区域选择性进行；在所有情况下，C中最缺乏电子的碳原子起始炔基戊烯的C键加到叠氮基内鎓盐的侧链碳上。炔基戊烯与叠氮化或其他1,3-偶极试剂的1,3-偶极环加成反应可以被视为杂联芳基的另一种合成方法。
• Synthesis and some properties of alkynyl derivatives of 1,3-dialkylperimidones. An example of the 1,2-palladium migration in the Sonogashira reaction
  作者：Ekaterina A. Filatova、Anna V. Gulevskaya、Alexander F. Pozharskii、Valery A. Ozeryanskii

  DOI：10.1016/j.tet.2016.02.003

  日期：2016.3

  Pd(II)-X group in the intermediate complex. Several peri-dialkynyl perimidones were tested for thermal or electrophile-initiated cyclizations resulting in the formation of some new polynuclear heterocyclic compounds, mostly derivatives of 3,5-diazadibenzo[cd,k]fluoranthene. The cyclizations have been found to proceed with more difficulty than those of 1,8-bis(phenylethynyl)naphthalene. This fact was ascribed

  从相应的溴化物通过以下方法获得了一系列的1,3-二甲基-1,3-二乙基-1 H -perimidine-2（3 H）-one的单，二，三和四炔基衍生物。Sonogashira反应。结果发现，将两个三甲基甲硅烷基乙炔基基团放置在perimidone的6和7位（peri）会形成空间受阻的系统，有时还会伴随着以前未知的Pd（II）-X基团的1,2-迁移。中间复合体。几个围-dialkynyl perimidones被用于产生一些新的多核杂环化合物，大多3,5-二苯并衍生物的形成热或亲电引发的环化反应[测试光盘，ķ]荧蒽。已经发现环化比1,8-双（苯基乙炔基）萘的环化困难得多。这一事实归因于萘部分的较大的面内变形的perimidones的结果在移动围彼此分开-炔基的基团。
• A mechanistic rationale for the outcome of Sonogashira cross-coupling of 9-bromoanthracene and ethynyltrimethylsilane: An unexpected product 4-(9-anthracenyl)-1,3-bis(trimethylsilyl)-3-en-1-yne
  作者：Kirill Nikitin、Helge Müller-Bunz、Patrick J. Guiry、Michael J. McGlinchey

  DOI：10.1016/j.jorganchem.2018.10.015

  日期：2019.2

  The Sonogashira reaction of 9-bromoanthracene and ethynyltrimethylsilane furnishes not only the anticipated 9-(trimethylsilylethynyl)anthracene and 2-(trimethylsilyl)aceanthrylene but also (E)-4-(9-anthracenyl)-1,3-bis(trimethylsilyl)-but-3-en-1-yne, all in moderate yields. A mechanistic rationale is proposed that invokes the intermediacy of bromo(anthracenyl)bis(triphenylphosphine)palladium(II) that can undergo coupling either directly, or after coordination and migratory insertion of the free alkyne. (C) 2018 Elsevier B.V. All rights reserved.
• NITROGENATED HETEROCYCLIC DERIVATIVE, ELECTRON-TRANSPORTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, AND ORGANIC ELECTROLUMINESCENT ELEMENT USING SAME
  申请人：Mizutani Sayaka

  公开号：US20130306955A1

  公开（公告）日：2013-11-21

  A specific nitrogen-containing heterocyclic compound having a urea structure, an electron transporting material containing the nitrogen-containing heterocyclic compound, and an organic electroluminescence device including a light emitting layer and an electron transporting layer between a cathode and an anode in which the electron transporting layer includes the electron transporting material or the nitrogen-containing heterocyclic derivative. An organic EL device exhibiting high emission efficiency even at low voltage and a material for organic EL devices are described.
• US9748496B2
  申请人：——

  公开号：US9748496B2

  公开（公告）日：2017-08-29