2-(furan-3-yl)benzo[d]oxazole | 83318-26-7

• 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-(furan-3-yl)benzo[d]oxazole
• 英文别名: 2-(3-furyl)benzo[d]oxazole；2-(furan-3-yl)benzoxazole；2-(3-Furyl)benzoxazole；2-(furan-3-yl)-1,3-benzoxazole
• CAS: 83318-26-7
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: RBLAYFSXIHSTTL-UHFFFAOYSA-N

物化性质

• 熔点：
  104-107 °C(Solv: hexane (110-54-3))
• 沸点：
  271.5±23.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 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：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  prop-2-enyl 2-thioxo-3H-benzoxazole-3-carboxylate 以 苯 为溶剂， 20.0~180.0 ℃ 、399.97 Pa 条件下， 生成 2-(furan-3-yl)benzo[d]oxazole
  参考文献：
  名称：

  苯并恶唑-2（3 H）-硫酮与环烯烃和杂芳族化合物的光加成反应

  摘要：

  苯并恶唑-2-硫酮的光加成反应1与环烯烃2和杂芳族化合物3进行了检查。的照射Ñ -acylbenzoxazole -2-硫酮1A和1B，和3-（甲氧羰基） -苯并恶唑-2-和3-（苯氧基羰基）（3 ħ）-thiones（1F和1H。，RESP）在环烯烃的存在2A -图2c，环己-1,4-二烯（2D）和茚（2E），得到2-取代的苯并恶唑4 - 13，18和19，和iminothietanes 14- 17，由两性离子中间体的硫醇盐阴离子的酰基或MeOCO和PhOCO基团的分子内俘获我和由两性离子中间体的酚盐阴离子II，分别从螺环氨基thietanes衍生AT通过形成[2 + 2] 1的CS键和2的CC键的环加成。在杂芳族化合物3的存在下照射1只能得到2-取代的苯并恶唑20 – 33。

  DOI：

  10.1002/hlca.200390266

文献信息

• A General Method for Suzuki–Miyaura Coupling Reactions Using Lithium Triisopropyl Borates
  作者：Matthias A. Oberli、Stephen L. Buchwald

  DOI：10.1021/ol302063g

  日期：2012.9.7

  Conditions for the Suzuki–Miyaura coupling of lithium triisopropyl borates are reported, as well as a procedure for a one-pot lithiation, borylation, and subsequent Suzuki–Miyaura coupling of various heterocycles with aryl halides. These borate species are much more stable toward protodeboronation than the corresponding boronic acids and can conveniently be stored on benchtop at room temperature.

  报道了三异丙基硼酸锂 Suzuki-Miyaura 偶联的条件，以及各种杂环与芳基卤化物的单锅锂化、硼酸化和随后的 Suzuki-Miyaura 偶联的程序。这些硼酸盐比相应的硼酸对原脱硼更稳定，可以方便地在室温下储存在台式上。
• Decarbonylative C–H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
  作者：Kazuma Amaike、Kei Muto、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1021/ja306062c

  日期：2012.8.22

  A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.
• A Facile Synthesis of 2-Substituted Benzoxazoles
  作者：Masanao Terashima、Masako Ishii、Yuichi Kanaoka

  DOI：10.1055/s-1982-29847

  日期：——
• A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay
  作者：Dhanusu Suresh、Amarajothi Dhakshinamoorthy、Kasi Pitchumani

  DOI：10.1016/j.tetlet.2013.09.039

  日期：2013.11

  A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives are synthesized in high yields without affecting many functional groups. Hot filtration experiments showed the absence of metal leaching and catalyst can be reused for five times with only a slight decrease in yield. (C) 2013 Elsevier Ltd. All rights reserved.
• Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water
  作者：Nekane Barbero、Mónica Carril、Raul SanMartin、Esther Domínguez

  DOI：10.1016/j.tet.2007.08.013

  日期：2007.10

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.