2-(4-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole | 851513-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole
• 英文别名: 2-[4-(Trifluoromethyl)-2-biphenylyl]-2-oxazoline；2-[2-phenyl-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazole
• CAS: 851513-80-9
• 化学式: C₁₆H₁₂F₃NO
• 分子量: 291.273
• InChiKey: DCTTUYDIJJPKOL-UHFFFAOYSA-N

物化性质

• 沸点：
  384.3±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole 、 氯甲酸甲酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Practical reduction of oxazolines to alcohols

  摘要：

  A two-step, one-pot procedure using methyl chloroformate and lithium borohydride was developed to transform 2-substituted-oxazolines into alcohols. This methodology is compatible with a wide range of Substrates including heterocyclic, aromatic, and aliphatic functionalized 2-oxazolines. Best results are obtained with electron-rich and ortho substituted 2-aryl-oxazolines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.061
• 作为产物：
  描述：

  溴苯 、 2-(3-(trifluoromethyl)phenyl)-4,5-dihydrooxazole 在 C₁₃H₁₇Cl₂O₆Ru₂^(1-)*Na⁽¹⁺⁾ 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 4.0h， 以94%的产率得到2-(4-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  芳烃钌催化剂MCAT-53通过芳族C–H键活化来合成水中的杂二芳基化合物

  摘要：

  已开发出一种新型的水友好型MCAT-53 [Ru 2 Cl 2（HCOO）3（对-cymene）] Na（η-6-对-cymene二氯二钌三甲酚络合物钠）作为实现芳族CH键的催化剂水中的活化和CC偶联反应。交叉偶联反应在无空气和无配体的条件下在去离子水/蒸馏水中进行，无需进一步活化催化剂。已经证明，使用MCAT-53催化剂可在水中合成CETP抑制剂Anacetrapib的高级中间体，从而生成单一的区域异构体。

  DOI：

  10.1021/acs.oprd.8b00141

文献信息

• [EN] RUTHENIUM-CATALYZED SYNTHESIS OF BIARYL COMPOUNDS IN WATER<br/>[FR] SYNTHÈSE DE COMPOSÉS BIARYLES DANS L'EAU CATALYSÉE PAR DU RUTHÉNIUM
  申请人：CHICAGO DISCOVERY SOLUTIONS LLC

  公开号：WO2015054120A1

  公开（公告）日：2015-04-16

  Using a [RuCl2(arene)]2 complex and a formate source, a directed ortho C-H insertion and aryl-aryl coupling sequence in water provides biaryl compounds useful in the preparation of biologically active molecules and intermediates. Reactions may be conducted in the ambient atmosphere. Ruthenium catalysts prepared from [RuCl2(arene)]2 and a formate source may be prepared in situ or isolated for later use.

  利用[RuCl2(芳烃)]2配合物和甲酸盐作为原料，在水中进行定向正交C-H插入和芳基-芳基偶联序列反应，可提供在制备生物活性分子和中间体中有用的联苯化合物。反应可在常温下进行。从[RuCl2(芳烃)]2和甲酸盐制备的钌催化剂可原位制备或隔离以供以后使用。
• Ruthenium-catalyzed synthesis of biaryl compounds in water
  申请人：CHICAGO DISCOVERY SOLUTIONS, LLC

  公开号：US10300471B2

  公开（公告）日：2019-05-28

  Using a [RuCl2(arene)]2 complex and a formate source, a directed ortho C—H insertion and aryl-aryl coupling sequence in water provides biaryl compounds useful in the preparation of biologically active molecules and intermediates. Reactions may be conducted in the ambient atmosphere. Ruthenium catalysts prepared from [RuCl2(arene)]2 and a formate source may be prepared in situ or isolated for later use.

  利用[RuCl2(arene)]2 复合物和甲酸盐源，在水中进行定向正交 C-H 插入和芳基-芳基偶联反应，可得到有助于制备生物活性分子和中间体的双芳基化合物。反应可在环境气氛中进行。由[RuCl2(arene)]2 和甲酸源制备的钌催化剂可就地制备或分离出来备用。
• RUTHENIUM-CATALYZED SYNTHESIS OF BIARYL COMPOUNDS IN WATER
  申请人：CHICAGO DISCOVERY SOLUTIONS, LLC

  公开号：US20160263565A1

  公开（公告）日：2016-09-15

  Using a [RuCl 2 (arene)] 2 complex and a formate source, a directed ortho C—H insertion and aryl-aryl coupling sequence in water provides biaryl compounds useful in the preparation of biologically active molecules and intermediates. Reactions may be conducted in the ambient atmosphere. Ruthenium catalysts prepared from [RuCl 2 (arene)] 2 and a formate source may be prepared in situ or isolated for later use.
• Practical reduction of oxazolines to alcohols
  作者：Anna Bernardi、Stéphane G. Ouellet、Remy Angelaud、Paul D. O’Shea

  DOI：10.1016/j.tetlet.2008.09.061

  日期：2008.11

  A two-step, one-pot procedure using methyl chloroformate and lithium borohydride was developed to transform 2-substituted-oxazolines into alcohols. This methodology is compatible with a wide range of Substrates including heterocyclic, aromatic, and aliphatic functionalized 2-oxazolines. Best results are obtained with electron-rich and ortho substituted 2-aryl-oxazolines. (c) 2008 Elsevier Ltd. All rights reserved.
• Arene Ruthenium Catalyst MCAT-53 for the Synthesis of Heterobiaryl Compounds in Water through Aromatic C–H Bond Activation
  作者：Anita Mehta、Biswajit Saha、Ali Aiden Koohang、Mukund S. Chorghade

  DOI：10.1021/acs.oprd.8b00141

  日期：2018.9.21

  developed as a catalyst to effect aromatic C–H bond activation and C–C coupling reactions in water. Cross-coupling reactions were performed in DI/distilled water under air- and ligand-free conditions without further activation of the catalyst. Synthesis of an advanced intermediate of CETP inhibitor, Anacetrapib, in water has been demonstrated to give a single regioisomer using the MCAT-53 catalyst.

  已开发出一种新型的水友好型MCAT-53 [Ru 2 Cl 2（HCOO）3（对-cymene）] Na（η-6-对-cymene二氯二钌三甲酚络合物钠）作为实现芳族CH键的催化剂水中的活化和CC偶联反应。交叉偶联反应在无空气和无配体的条件下在去离子水/蒸馏水中进行，无需进一步活化催化剂。已经证明，使用MCAT-53催化剂可在水中合成CETP抑制剂Anacetrapib的高级中间体，从而生成单一的区域异构体。