2-(2,4-dichlorophenyl)-1,3-benzoxazole | 3164-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,4-dichlorophenyl)-1,3-benzoxazole
• 英文别名: 2-(2,4-dichlorophenyl)benzo[d]oxazole；2-(2,4-dichlorophenyl)benzoxazole
• CAS: 3164-11-2
• 化学式: C₁₃H₇Cl₂NO
• mdl: MFCD00441566
• 分子量: 264.111
• InChiKey: UHLGOZRQHWGNEB-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  354.3±32.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 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：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,4-dichlorophenyl)-1,3-benzoxazole 在 dipotassium peroxodisulfate 、 silver(I) nitrite 、 氧气 、 palladium diacetate 作用下， 反应 42.0h， 以87%的产率得到2-(2,4-dichloro-6-nitrophenyl)benzo[d]oxazole
  参考文献：
  名称：

  Palladium-catalyzed ortho-nitration of 2-arylbenzoxazoles

  摘要：

  An efficient and general protocol for palladium-catalyzed chelation-assisted ortho-nitration of 2-arylbenzoxazoles has been developed. This nitration exhibits high regioselectivity for the substrates, and the reaction could tolerate many functional groups such as F, Cl, Br, CH3, CH3O, affording ortho-nitration products in moderate to good yields. Moreover, some 2-arylbenzoxazole heterocyclic analogues proceed well under this catalytic system. Further studies have been performed to obtain insight into the mechanism. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.035
• 作为产物：
  描述：

  (E)-2-((2,4-dichlorobenzylidene)amino)phenol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 eosin Y bis(tetrabutyl ammonium salt) 作用下， 20.0 ℃ 、101.33 kPa 条件下， 以71%的产率得到2-(2,4-dichlorophenyl)-1,3-benzoxazole
  参考文献：
  名称：

  Synthesis of 2-substituted pyrimidines and benzoxazoles via a visible-light-driven organocatalytic aerobic oxidation: enhancement of the reaction rate and selectivity by a base

  摘要：

  利用有机光催化剂藻红Y双(四丁基铵盐)(TBA-藻红Y)和廉价氧化剂分子氧，已经实现了各种2-取代二氢嘧啶和酚亚胺的高效可见光驱动光催化氧化反应。在碱的辅助下，从底物二氢嘧啶或酚亚胺到TBA-藻红Y激发态的显著增强的光诱导电子转移，使得空气氧化能够选择性地生成2-(甲硫基)嘧啶或2-芳基苯并噁唑。

  DOI：

  10.1039/c4gc00337c

文献信息

• Palladium-catalyzed deamidative arylation of azoles with arylamides through a tandem decarbonylation–C–H functionalization
  作者：Chengliang Li、Pinhua Li、Jin Yang、Lei Wang

  DOI：10.1039/c2cc18156h

  日期：——

  A highly chemo-, regio-selective, and efficient palladium-catalyzed deamidative arylation of azoles with arylamides, as an aryl metal equivalent, has been developed. The reaction proceeds smoothly to generate the corresponding products in good yields via a tandem decarbonylation–C–H activation.

  一种高化学选择性、区域选择性和高效的钯催化脱酰胺化芳基化反应已被开发出来，用于含有芳基酰胺的咪唑类化合物的反应，将其作为芳基金属等价物。该反应通过串联的去羰化-C-H活化顺利进行，以良好的产率生成了相应的产物。
• Base-Free Selective <i>O</i> -Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles
  作者：Wei-Min Shi、Xiao-Hua Li、Cui Liang、Dong-Liang Mo

  DOI：10.1002/adsc.201700906

  日期：2017.12.11

  of functionalized 2‐substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selective O‐arylation and sequential [3,3]‐rearrangement under metal‐free conditions. O‐arylation of amidoximes was promoted by 3 Å molecule sieves in the absence of a base and a sequential TFA‐mediated [3,3]‐rearrangement was used to synthesize 2‐substituted benzoxazoles. Both of

  在无金属条件下，可以通过选择性O芳基化和顺序[3,3]重排，从ox胺肟和二芳基碘鎓盐中以高收率制备各种功能化的2-取代苯并恶唑。ø偕胺肟的-arylation用3埃分子筛在不存在碱的和促进连续TFA介导的，使用[3,3] -rearrangement以合成2-取代的苯并恶唑。两者的ø -芳基产品和重排产物用宽范围敏感的官能团，如酯，醛，硝基，乙烯基，胺和酰胺基团除了卤化物的兼容。分两步以克规模制备了带有双苯并恶唑的双齿N-配体。
• Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by <i>ortho</i>-Quinone Catalysis
  作者：Ruipu Zhang、Yan Qin、Long Zhang、Sanzhong Luo

  DOI：10.1021/acs.orglett.7b02786

  日期：2017.10.20

  The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.

  生物启发的邻醌催化剂已被用于杂环的合成。在没有任何金属助催化剂的情况下，单一的邻醌催化剂能够在温和的条件下，以氧气为末端氧化剂，以高收率从伯胺氧化合成苯并咪唑，喹喔啉和苯并恶唑。
• One-pot Synthesis of 2-Substituted Benzoxazoles Promoted by Copper Acetate Monohydrate
  作者：Guo-Feng Chen、Hai-Dong Shen、Li-Yan Zhang、Hong-Yang Li、Rui-Jia Lan、Bao-Hua Chen、Ji-Tai Li、Qing-Hui Hu

  DOI：10.2174/15701786113106660070

  日期：2014.2

  An efficient synthesis of 2-substituted benzoxazoles via copper acetate monohydrate oxidative coupling of aldehydes with o-aminophenol is described. This synthetic strategy has some advantages as simple procedure, inexpensive and easily available catalyst, and facile isolation of the products in moderate to good yields.

  描述了一种通过醛与邻氨基酚的铜醋酸盐单水合物氧化偶联反应高效合成2取代苯并噁唑的方法。该合成策略具有一些优点，如操作简便、催化剂廉价且易于获取，以及在中等至良好产率下方便分离产品。
• Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One-pot Synthesis of Benzoxazoles
  作者：Firouz Matloubi Moghaddam、Vahid Saberi、Sepideh Kalhor、Nazila Veisi

  DOI：10.1002/aoc.4240

  日期：2018.4

  Palladium(II) have been immobilized into the nano magnetic Fe3O4 which was functionalized with glucose in order to achieve a one‐pot synthesis of 2‐substituted benzoxazole derivatives with high yields in the diverse range of organic solvents. The nano catalyst is highly dispersive in polar solvents and can be easily recovered and reused for 6 runs without significant loss of its activity. Finally,

  钯（II）已被固定在纳米磁性的Fe 3 O 4中，并用葡萄糖对其进行了功能化，以便在各种有机溶剂中以高收率一次合成2取代的苯并恶唑衍生物。纳米催化剂在极性溶剂中具有高度分散性，可以轻松回收并重复使用6次，而不会显着降低其活性。最后，通过FT-IR，TGA，CHN，SEM，EDX和原子吸收光谱对催化剂进行了全面表征。