2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole | 15952-19-9

• 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-(3-(trifluoromethyl)phenyl)benzo[d]oxazole
• 英文别名: 2-(3-(Trifluoromethyl)phenyl)benzoxazole；2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazole
• CAS: 15952-19-9
• 化学式: C₁₄H₈F₃NO
• 分子量: 263.219
• InChiKey: YXFPRGSDFHEAFV-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  306.4±42.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(2-Hydroxy-phenyl)-3-trifluoromethyl-benzamide 在 对甲苯磺酸 作用下， 以 xylene 为溶剂， 反应 5.0h， 以109 mg的产率得到2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole
  参考文献：
  名称：

  Biochemical and Structural Evaluation of Highly Selective 2-Arylbenzoxazole-Based Transthyretin Amyloidogenesis Inhibitors

  摘要：

  To develop potent transthyretin (TTR) amyloidogenesis inhibitors that also display high binding selectivity in blood, it proves useful to systematically optimize each of the three substructural elements that comprise a typical inhibitor: the two aryl rings and the linker joining them. In the first study, described herein, structural modifications to one aryl ring were evaluated by screening a library of 2-arylbenzoxazoles bearing thyroid hormone-like aryl substituents on the 2-aryl ring. Several potent and highly selective amyloidogenesis inhibitors were identified that exhibit minimal thyroid hormone nuclear receptor and COX-1 binding. High resolution crystal structures (1.3-1.5 angstrom) of three inhibitors (2f, 4f, and 4d) in complex with TTR were obtained to characterize their binding orientation. Collectively, the results demonstrate that thyroid hormone-like substitution patterns on one aryl ring lead to potent and highly selective TTR amyloidogenesis inhibitors that lack undesirable thyroid hormone receptor or COX-1 binding.

  DOI：

  10.1021/jm0708735

文献信息

• Palladium-catalyzed desulfitative arylation of azoles with arylsulfonyl hydrazides
  作者：Xinzhang Yu、Xingwei Li、Boshun Wan

  DOI：10.1039/c2ob26270c

  日期：——

  Palladium-catalyzed desulfitative and denitrogenative arylation of azoles with arylsulfonyl hydrazides has been achieved. A broad scope of azoles and arylsulfonyl hydrazides has been used to produce arylated azoles in high yields.

  已经实现了钯与芳基磺酰基酰肼的钯催化的脱硫和脱氮芳基化反应。各种各样的唑和芳基磺酰肼已被用于高产率地生产芳基化的唑。
• Nickel-Catalyzed Coupling of Azoles with Aromatic Nitriles
  作者：Mckenna G. Hanson、Noelle M. Olson、Zubaoyi Yi、Grace Wilson、Dipannita Kalyani

  DOI：10.1021/acs.orglett.7b01938

  日期：2017.8.18

  This manuscript describes the Ni-catalyzed coupling of azoles with aromatic nitriles. The use of BPh3 promotes these arylations with electronically diverse azoles and benzonitriles. While the nickel catalyst is necessary for the arylations of phenyl oxazoles, arylation of benzoxazoles with some nitriles affords the arylated products even in the absence of the Ni catalyst albeit in lower yield than

  该手稿描述了Ni催化的唑类化合物与芳族腈的偶联。BPh 3的使用可促进电子形式多样的唑和苄腈的这些芳基化。尽管镍催化剂对于苯基恶唑的芳基化是必需的，但是即使在不存在Ni催化剂的情况下，苯并恶唑与某些腈的芳基化也可以提供芳基化的产物，尽管收率比催化方法低。与未催化的转化相比，镍催化的方法显示出更高的速率和更广阔的范围。
• Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides
  作者：Feng Gao、Byeong-Seon Kim、Patrick J. Walsh

  DOI：10.1039/c4cc05307a

  日期：——

  The first room-temperature direct 2-arylation of benzoxazoles with aryl bromides by a Pd(OAc)₂/NiXantphos-based catalyst is reported.

  第一个室温下使用Pd(OAc)₂/NiXantphos基催化剂对苯并噁唑与芳基溴化物进行直接2-芳基化反应的研究结果已经报道。
• Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
  作者：Nidhi Mishra、Anoop S. Singh、Anand K. Agrahari、Sumit K. Singh、Mala Singh、Vinod K. Tiwari

  DOI：10.1021/acscombsci.9b00004

  日期：2019.5.13

  and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles

  糖基三唑可以方便地获得，并且包含多个金属结合单元，可以协助金属介导的催化作用。d-葡萄糖的叠氮化物衍生物已被转化为它们各自的芳基三唑，并被筛选为通过铜催化的分子内Ullmann型C-杂原子偶联合成2-取代的苯并稠合的唑和苯并咪唑并喹唑啉酮的配体。对于这种容易获得的催化体系，获得了多种苯并稠合杂环的良好或优异的产率。
• Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates
  作者：Lutz Ackermann、Andreas Althammer、Sabine Fenner

  DOI：10.1002/anie.200804517

  日期：2009.1

  A toss up: A highly active palladium complex enabled the first direct arylation of heteroarenes through CH bond functionalization using tosylates or mesylates as electrophiles with ample scope.

  抛弃：高活性的钯络合物可以使用甲苯磺酸盐或甲磺酸盐作为亲电试剂，通过CH键官能化，使杂芳烃首次直接芳基化，且具有足够的范围。