(R)-2,5-diphenyloxazoline

• 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: (R)-2,5-diphenyloxazoline
• 英文别名: oxytriphine；(5R)-2,5-diphenyl-4,5-dihydro-1,3-oxazole
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: AORHJOUBDGUERJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2,5-diphenyloxazoline 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以98%的产率得到(R)-N-(2-hydroxy-2-phenylethyl)benzamide
  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：

  2,5-二苯基恶唑 在 [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) 、 C₄₈H₄₄Fe₂P₂ 、 氢气 、 四甲基胍 作用下， 以 异丁醇 为溶剂， 反应 4.0h， 以97%的产率得到(R)-2,5-diphenyloxazoline
  参考文献：
  名称：

  杂芳烃和芳烃的催化不对称氢化

  摘要：

  图形摘要 摘要 转螯合手性双膦 PhTRAP 允许钌催化的各种唑类氢化反应以高对映选择性进行。PhTRAP-钌催化剂将吲哚、吡咯、咪唑和恶唑转化为相应的手性杂环。萘也被手性钌催化剂用氢还原，专门得到四氢化萘。从相应的取代萘的催化不对称氢化中获得了一些具有超过 90% ee 的 2-烷氧基四氢化萘。

  DOI：

  10.1080/10426507.2014.974752

文献信息

• Chiral Hypervalent Iodine Catalysis Enables an Unusual Regiodivergent Intermolecular Olefin Aminooxygenation
  作者：Fan Wu、Navdeep Kaur、Nur-E Alom、Wei Li

  DOI：10.1021/jacsau.1c00103

  日期：2021.6.28

  strategy is described here. Amide is used as the O- and N- source to probe for regiocontrol strategies. Notably, simple additives can be selectively introduced to achieve regiodivergent oxyamination processes for electronically activated alkenes while being regio-complementary for unactivated alkenes. Our preliminary data demonstrates that this regiocontrol strategy based on nucleophile can also be applied

  本文描述了一种新型碘化物催化分子间氨氧化策略。酰胺用作 O 源和 N 源来探测区域控制策略。值得注意的是，可以选择性地引入简单的添加剂，以实现电子活化烯烃的区域发散的氧胺化过程，同时对未活化的烯烃进行区域互补。我们的初步数据表明，这种基于亲核试剂的区域控制策略也可以应用于使用手性高价碘催化的不对称过程。
• 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.
• Catalytic Asymmetric Hydrogenation of Heteroarenes and Arenes
  作者：Ryoichi Kuwano

  DOI：10.1080/10426507.2014.974752

  日期：2015.6.3

  ruthenium-catalyzed hydrogenation of various azoles to proceed with high enantioselectivity. The PhTRAP–ruthenium catalyst transformed indoles, pyrroles, imidazoles, and oxazoles into the corresponding chiral heterocycles. Naphthalenes are also reduced with hydrogen by the chiral ruthenium catalyst, exclusively giving tetralins. Some 2-alkoxytetralins were obtained with over 90% ee from the catalytic asymmetric hydrogenation

  图形摘要 摘要 转螯合手性双膦 PhTRAP 允许钌催化的各种唑类氢化反应以高对映选择性进行。PhTRAP-钌催化剂将吲哚、吡咯、咪唑和恶唑转化为相应的手性杂环。萘也被手性钌催化剂用氢还原，专门得到四氢化萘。从相应的取代萘的催化不对称氢化中获得了一些具有超过 90% ee 的 2-烷氧基四氢化萘。