(+)-2-phenyl-4-[4-(trifluoromethyl)phenyl]oxazoline

• 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-phenyl-4-[4-(trifluoromethyl)phenyl]oxazoline
• 英文别名: 2-Phenyl-4-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazole；(4R)-2-phenyl-4-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazole
• 化学式: C₁₆H₁₂F₃NO
• 分子量: 291.273
• InChiKey: YUGOKYKYWNKFII-AWEZNQCLSA-N

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

• 作为产物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 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 、 甲苯 为溶剂， 80.0 ℃ 、5.07 MPa 条件下， 反应 76.0h， 生成 (+)-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

文献信息

• Enantioselective radical C–H amination for the synthesis of β-amino alcohols
  作者：Kohki M. Nakafuku、Zuxiao Zhang、Ethan A. Wappes、Leah M. Stateman、Andrew D. Chen、David A. Nagib

  DOI：10.1038/s41557-020-0482-8

  日期：2020.8

  but powerful tools for solving modern synthetic challenges. Specifically, the enantio- and regioselective C–H amination of alcohols to access medicinally valuable chiral β-amino alcohols remains elusive. To solve this challenge, a radical relay chaperone strategy was designed, wherein an alcohol was transiently converted to an imidate radical that underwent intramolecular H-atom transfer (HAT). This regioselective

  不对称的基本C–H功能化是解决现代综合挑战的罕见但功能强大的工具。特别是，醇的对映体和区域选择性C–H胺化以获取具有医学价值的手性β-氨基醇仍然难以实现。为了解决这一挑战，设计了一种自由基中继分子伴侣策略，其中将一种醇瞬态转化为经过分子内H原子转移（HAT）的亚氨酸酯自由基。通过利用能量转移催化来介导选择性自由基的产生和被手性铜催化剂的拦截，该区域选择性HAT也被赋予了对映选择性。这种多催化，不对称自由基C–H胺的成功开发，使人们能够广泛地从多种含有烷基，烯丙基，苄基和炔丙基C–H键的醇中获得手性β-氨基醇。
• Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles
  作者：Ryoichi Kuwano、Nao Kameyama、Ryuhei Ikeda

  DOI：10.1021/ja201543h

  日期：2011.5.18

  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.