2-phenyl-4-(4-(trifluoromethyl)phenyl)oxazole | 897027-52-0

• 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-phenyl-4-(4-(trifluoromethyl)phenyl)oxazole
• 英文别名: 2-Phenyl-4-[4-(trifluoromethyl)phenyl]oxazole；2-phenyl-4-[4-(trifluoromethyl)phenyl]-1,3-oxazole
• CAS: 897027-52-0
• 化学式: C₁₆H₁₀F₃NO
• 分子量: 289.257
• InChiKey: YHSBOAAMFREHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(4-(trifluoromethyl)phenyl)oxazole 在 [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) 、 (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene 、 氢气 、 四甲基胍 作用下， 以 异丁醇 为溶剂， 80.0 ℃ 、5.07 MPa 条件下， 反应 4.0h， 以90%的产率得到(+)-2-phenyl-4-[4-(trifluoromethyl)phenyl]oxazoline
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles

  摘要：

  Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(eta(3)-methallyl)(2)(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.

  DOI：

  10.1021/ja201543h
• 作为产物：
  描述：

  2-苯基-2-恶唑啉-4-酮 在 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.66h， 生成 2-phenyl-4-(4-(trifluoromethyl)phenyl)oxazole
  参考文献：
  名称：

  Suzuki Coupling of Oxazoles

  摘要：

  A protocol for the functionalization of the oxazole 2- and 4-positions using the Suzuki coupling reaction is described. 2-Aryl-4-trifloyloxazoles undergo rapid, microwave-assisted coupling with a range of aryl and heteroaryl boronic acids in good to excellent yields. The methodology is similarly effective using 4-aryl-2-chlorooxazoles as the coupling partner and has been extended to the synthesis of a novel class of homo-and heterodimeric 4,4-linked dioxazoles.

  DOI：

  10.1021/ol060591j

文献信息

• Divergent Palladium‐Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins
  作者：Ling Dai、Shuling Yu、Wenzhang Xiong、Zhongyan Chen、Tong Xu、Yinlin Shao、Jiuxi Chen

  DOI：10.1002/adsc.202000125

  日期：2020.4.27

  A palladium‐catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2‐position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl benzoates afforded 2,4‐diaryloxazoles as products, while 2‐benzoyl‐substituted cyanomethyl benzoates delivered 3‐benzoyl‐4‐aryl‐isocoumarins selectively

  已实现了氰基甲基苯甲酸酯与芳基硼酸的钯催化串联反应。已发现在氰基甲基苯甲酸酯的2位取代对于选择合成恶唑和异香豆素至关重要。氰基苯甲酸甲酯提供了2,4-二芳基恶唑，而2-苯甲酰基取代的氰基甲基苯甲酸酯则选择性地提供了3-苯甲酰基-4-芳基-异香豆素。此外，讨论了氰基甲基苯甲酸酯与芳基硼酸选择性反应的可能机理。
• Radical cascade synthesis of azoles <i>via</i> tandem hydrogen atom transfer
  作者：Andrew D. Chen、James H. Herbort、Ethan A. Wappes、Kohki M. Nakafuku、Darsheed N. Mustafa、David A. Nagib

  DOI：10.1039/c9sc06239d

  日期：——

  A radical cascade enables rapid, modular access to five-membered heteroarenes, including oxazoles and imidazoles, through a regio- and chemo-selective β C–H bis-functionalization.

  一种基本级联反应使得通过选择性的β C-H双官能团化，可以迅速、模块化地获得包括噁唑和咪唑在内的五元杂环芳烃。