2-(pyrimidin-5-yl)benzo[d]oxazole | 39116-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(pyrimidin-5-yl)benzo[d]oxazole
• 英文别名: 2-pyrimidin-5-ylbenzooxazole；2-pyrimidin-5-ylbenzoxazole；2-(5-pyrimidyl)benzoxazole；2-pyrimidin-5-yl-benzooxazole；5-(2-Benzoxazolyl)-pyrimidin；Benzoxazole, 2-(5-pyrimidinyl)-；2-pyrimidin-5-yl-1,3-benzoxazole
• CAS: 39116-33-1
• 化学式: C₁₁H₇N₃O
• 分子量: 197.196
• InChiKey: AUNVWPWAYXUTDA-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C
• 沸点：
  333.8±25.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  嘧啶-5-甲醛 在 碘苯二乙酸 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2-(pyrimidin-5-yl)benzo[d]oxazole
  参考文献：
  名称：

  1,2,3,4-四氢嘧啶-5-基苯并恶唑的便捷合成†

  摘要：

  通过使5-嘧啶甲醛4与取代的氨基酚5缩合，然后用碘代苯二乙酸酯将所得的席夫氏碱6氧化环化，可以合成2-嘧啶-5-基苯并恶唑7。随后形成甲基嘧啶鎓盐8，然后还原得到四氢嘧啶基苯并恶唑10。该方法已用于合成M 1毒蕈碱激动剂候选物中。

  DOI：

  10.1002/jhet.5570370447

文献信息

• Deprotonation of Benzoxazole and Oxazole Using Lithium Magnesates
  作者：Omar Bayh、Haçan Awad、Florence Mongin、Christophe Hoarau、Laurent Bischoff、François Trécourt、Guy Quéguiner、Francis Marsais、Fernando Blanco、Belén Abarca、Rafael Ballesteros

  DOI：10.1021/jo050493w

  日期：2005.6.1

  benzoxazole using lithium magnesates are described. The reactions occurred in tetrahydrofuran at room temperature using 1/3 equiv of lithium tributylmagnesate. As 2-lithiooxazole and 2-lithiobenzoxazole, lithium tri(2-oxazolyl)magnesate and lithium tri(2-benzoxazolyl)magnesate very rapidly and completely isomerized to the more stable 2-(isocyano)enolate and 2-(isocyano)phenolate type structures, respectively

  描述了使用镁酸锂对恶唑和苯并恶唑的第一次去质子化。该反应在室温下使用1/3当量的三丁基镁的锂在四氢呋喃中发生。作为2-lithiooxazole和2-lithiobenzoxazole，三（2-恶唑基）镁酸锂和三（2-苯并恶唑基）镁锂非常迅速且完全异构化为更稳定的2-（异氰基）烯酸酯和2-（异氰基）酚酸酯型结构分别通过NMR分析显示结果。亲电捕集后，以中等至高收率分离2-取代的恶唑和苯并恶唑的方法有两种：（1）开放结构和封闭结构之间的平衡比开放异构体的捕获快，封闭异构体的捕获率更高反应比开放的 或（2）开放异构体在分子内Passerini型反应中与亲电试剂反应。在不存在溴化锂的情况下，2-（异氰基）烯酸酯型结构对茴香醛的非反应性使分子内Passerini型反应更合理。
• An Iron and Copper System Catalyzed C–H Arylation of Azoles with Arylboronic­ Acids
  作者：Song-Lin Zhang、Wei-Ye Hu、Pei-Pei Wang

  DOI：10.1055/s-0034-1379073

  日期：——

  An efficient, environmentally friendly, and economical new method for arylation reactions of azoles with arylboronic acids via copper-iron-catalyzed C-H and C-B bond activation has been developed. The protocol tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, and trifluoromethyl groups.
• Chandramohan,M.R.; Seshadri,S., Indian Journal of Chemistry, 1972, vol. 10, p. 573 - 576
  作者：Chandramohan,M.R.、Seshadri,S.

  DOI：——

  日期：——
• Direct arylation of oxazole and benzoxazole with aryl or heteroaryl halides using a palladium–diphosphine catalyst
  作者：Fazia Derridj、Safia Djebbar、Ouassini Benali-Baitich、Henri Doucet

  DOI：10.1016/j.jorganchem.2007.10.028

  日期：2008.1

  Through the use of PdCl(dppb)(C3H5) as a catalyst, a range of aryl bromides and chlorides undergoes coupling via C-H bond activation/flunctionalization reaction with oxazole or benzoxazole in good yields. This air-stable catalyst can be used at low loadings with several substrates. Surprisingly, better results in terms of substrate/catalyst ratio were obtained in several cases using electron-excessive aryl bromides than with the electron-deficient ones. This seems to be mainly due to the relatively low thermal stability of some of the 2-arylbenzoxazoles formed with electron -deficient aryl halides. With these substrates, in order to obtain higher yields of product, the reactions had to be performed at a lower temperature (100-120 degrees C) using a larger amount of catalyst. On the other hand, in the presence of the most stable products, the reactions were performed at 150 degrees C using as little as 0.2 mol% catalyst. Arylation of benzoxazole with heteroaryl bromides also gave the coupling products in moderate to high yields using 0.2-5 mol% catalyst. With this catalyst, electron-deficient aryl chloride such as 4-chlorobenzonitrile, 4-chloroacetophenone or 2-chloronitrobenzene have also been used successfully. (c) 2007 Elsevier B.V. All rights reserved.
• Convenient synthesis of 1,2,3,4-tetrahydro-pyrimidin-5-ylbenzoxazoles
  作者：Myung Hee Jung、Sung-Won Choi、Kui-Woong Cho

  DOI：10.1002/jhet.5570370447

  日期：2000.7

  bases 6 with iodobenzene diacetate. Subsequent formation of methylpyrimidinium salts 8 and reduction thereafter afforded tetrahydropyrimidinylbenzoxazoles 10. This method has been utilized in the synthesis of M1 muscarinic agonist candidates.

  通过使5-嘧啶甲醛4与取代的氨基酚5缩合，然后用碘代苯二乙酸酯将所得的席夫氏碱6氧化环化，可以合成2-嘧啶-5-基苯并恶唑7。随后形成甲基嘧啶鎓盐8，然后还原得到四氢嘧啶基苯并恶唑10。该方法已用于合成M 1毒蕈碱激动剂候选物中。

表征谱图