5-(2-呋喃基)嘧啶 | 63558-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(2-呋喃基)嘧啶
• 英文名称: 5-(furan-2-yl)pyrimidine
• 英文别名: 5-(2-Furyl)pyrimidin
• CAS: 63558-71-4
• 化学式: C₈H₆N₂O
• 分子量: 146.148
• InChiKey: SIPOYUWCPURHBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(2-呋喃基)嘧啶 、 2-溴苯乙酮 以 乙腈 为溶剂， 反应 168.0h， 生成 5-(2-furyl)-N-phenacylpyrimidinium bromide
  参考文献：
  名称：

  Allen, David W.; Buckland, David J.; Hutley, Barrie G., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 4, p. 468 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  呋喃 、 5-碘嘧啶 以 乙腈 为溶剂， 生成 5-(2-呋喃基)嘧啶
  参考文献：
  名称：

  Allen,D.W. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 621 - 624

  摘要：

  DOI：

文献信息

• Synthesis of Amido-N-imidazolium Salts and their Applications as Ligands in Suzuki-Miyaura Reactions: Coupling of Hetero- aromatic Halides and the Synthesis of Milrinone and Irbesartan
  作者：Manian Rajesh Kumar、Kyungho Park、Sunwoo Lee

  DOI：10.1002/adsc.201000592

  日期：2010.12.17

  catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki–Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki–Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to

  描述了基于钯-酰胺基-N-杂环卡宾的Suzuki-Miyaura杂芳基溴化物偶联反应的新催化体系。从相应的苯胺以高收率合成了各种空间庞大的酰胺基-N-咪唑鎓盐。该催化体系有效地促进了杂芳基溴化物和氯化物与一系列硼酸的Suzuki-Miyaura偶联，从而以高收率得到了相应的芳基化合物。随着取代基空间位阻的增加，产率增加。特别是，1-（2,6-二异丙基）-3- ñ - （2,4,6-三-叔-butylphenylacetamido）咪唑鎓溴化物（4BC）在2-溴吡啶和苯基硼酸的偶联反应中显示出850,000 TON。此外，药物化合物如米力农和厄贝沙坦是通过Suzuki-Miyaura偶联，使用体积庞大的酰胺基-N-咪唑鎓盐（4bc）作为配体合成的。
• Solvent‐Free, Palladium‐Catalyzed Suzuki–Miyaura Cross‐Couplings of Aryl Chlorides with Arylboronic Acids
  作者：Jin‐Heng Li、Chen‐Liang Deng、Ye‐Xiang Xie

  DOI：10.1080/00397910701412828

  日期：2007.7

  Abstract Pd(MeCN)2Cl2/PCy3 was found to be an efficient catalytic system for the Suzuki–Miyaura cross‐couplings of aryl chlorides with arylboronic acids under solvent‐free conditions. Furthermore, the presence of the conventional solvents had deleterious effect on the reaction. In the presence of Pd(MeCN)2Cl2, PCy3, and TBAF (tetra‐n‐butylammonium fluoride), a number of aryl chlorides including heteroaryl

  摘要 Pd(MeCN)2Cl2/PCy3 被发现是在无溶剂条件下芳基氯与芳基硼酸 Suzuki-Miyaura 交叉偶联的有效催化体系。此外，常规溶剂的存在对反应具有有害影响。在 Pd(MeCN)2Cl2、PCy3 和 TBAF（四正丁基氟化铵）存在下，包括杂芳基氯在内的多种芳基氯与芳基硼酸或杂芳基硼酸顺利偶联，以中等至优异的收率得到相应的产物.
• Highly Reactive, Single-Component Nickel Catalyst Precursor for Suzuki-Miyuara Cross-Coupling of Heteroaryl Boronic Acids with Heteroaryl Halides
  作者：Shaozhong Ge、John F. Hartwig

  DOI：10.1002/anie.201207428

  日期：2012.12.14

  One for all: The coupling of a range of nitrogen‐ and sulfur‐containing heteroaryl halides with five‐membered nitrogen‐, oxygen‐, and sulfur‐containing heteroaryl boronic acids were achieved in high yields with only 0.5 mol % of the single‐component nickel precatalyst [(dppf)NiCl(cinnamyl)] (dppf=1,1′‐bis(diphenylphosphanyl)ferrocene). The reaction demonstrates good functional group compatibility,

  一劳永逸：一系列含氮和硫的杂芳基卤化物与五元含氮、氧和硫杂芳基硼酸的偶联以高产率实现，单组分仅为 0.5 mol%镍预催化剂 [(dppf)NiCl(肉桂基)] (dppf=1,1'-双(二苯基膦基)二茂铁)。该反应具有良好的官能团相容性，无需干燥箱即可大规模进行。
• Pd(OAc)2/DABCO-catalyzed Suzuki–Miyaura cross-coupling reaction in DMF
  作者：Jin-Heng Li、Qi-Ming Zhu、Ye-Xiang Xie

  DOI：10.1016/j.tet.2006.08.103

  日期：2006.11

  The scope and limitations of the Pd(OAc)(2)/DABCO (1,4-diaza-bicyclo[2.2.2]octane)-catalyzed Suzuki-Miyaura cross-coupling reactions have been demonstrated. The results showed that the effect of solvent had a fundamental influence on the reaction. In the presence of Pd(OAc)2 and DABCO, both aryl bromides and aryl chlorides all worked well with arylboronic acids to form biaryls, heteroaryl-aryls, and bibeteroaryls in moderate to excellent yields using DMF as the solvent. Additionally, the reactions of aryl bromides were conducted under relatively mild conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• ALLEN D. W.; BUCKLAND D. J.; HUTLEY B. G.; OADES A. C.; TURNER J. B., J. CHEM. SOC. PERKIN TRANS., 1977, PART 1,
  作者：ALLEN D. W.、 BUCKLAND D. J.、 HUTLEY B. G.、 OADES A. C.、 TURNER J. B.

  DOI：——

  日期：——