(S)-2,5-diphenyl-1,3-oxazoline | 87443-39-8

• 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: (S)-2,5-diphenyl-1,3-oxazoline
• 英文别名: (5S)-2,5-diphenyl-2-oxazoline；(S)-2,5-diphenyloxazoline；(5S)-2,5-Diphenyl-4,5-dihydro-1,3-oxazole
• CAS: 87443-39-8
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: AORHJOUBDGUERJ-CQSZACIVSA-N

物化性质

• 熔点：
  38-40 °C
• 沸点：
  373.2±31.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

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：

  (S)-2,5-diphenyl-1,3-oxazoline 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 2-(benzoylamino)-1-phenylethanol
  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：

  (R)-N-(2-hydroxy-2-phenylethyl)benzamide 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到(S)-2,5-diphenyl-1,3-oxazoline
  参考文献：
  名称：

  以PPh3-DDQ为脱水剂方便合成2-恶唑啉和2-苯并恶唑

  摘要：

  用三苯基膦-2,3-二氯-5,6-二氰基苯并醌（PPh 3 -DDQ）作为脱水和活化试剂分别从酰基氨基醇和酰基氨基苯酚分别以高收率合成了2-恶唑啉和2-苯并恶唑。该合成在中性条件下完成。

  DOI：

  10.1002/cjoc.201190190

文献信息

• An asymmetric synthesis of chiral phthalides via chiral lithiated oxazolines
  作者：A.I. Meyers、Mary Ann Hanagan、L.M. Trefonas、R.J. Baker

  DOI：10.1016/s0040-4020(01)91917-9

  日期：1983.1

  Chiral aromatic oxazolines were prepared for utilization in asymmetric C-C bonding reactions. Lithiation of aryloxazolines could not be accomplished directly but were efficiently lithiated via halogen metal exchange of the o-bromo derivative 16. The resulting lithio compound 9 reacted smoothly with carbonyls to give adducts 19 but with poor stereoselectivity. Hydrolysis gave the phthalides 4 in poor

  制备了用于不对称CC键合反应的手性芳族恶唑啉。芳基恶唑啉的锂化不能直接完成，而是通过邻溴衍生物16的卤素金属交换有效地被锂化。所得的硫代化合物9与羰基平稳反应，得到加合物19，但立体选择性差。水解得到的邻苯二甲酸酯4的ee较差（20–25％）。当将硫代恶唑啉9转化为21时，它们现在用作手性亲电子试剂。在21中添加有机金属尤其在格利雅试剂的帮助下，得到了有用水平的不对称诱导，水解后，得到的邻苯二甲酸盐含量为40-80％ee（4）。
• Microwave-assisted rapid synthesis of chiral oxazolines
  作者：Haowen Deng、Jianshe Wang、Wei He、Yang Ye、Renren Bai、Xuelei Zhang、Xiang-Yang Ye、Tian Xie、Zi Hui

  DOI：10.1039/d2ob02192g

  日期：——

  Chiral oxazoline compounds play an extremely important role in asymmetric synthesis and drug discovery. Herein a simpler, greener and more efficient microwave-assisted protocol to rapidly access chiral oxazolines is developed using aryl nitriles or cyano-containing compounds and chiral β-amino alcohols as starting materials. The reaction proceeds smoothly in the presence of a recoverable heterogeneous

  手性恶唑啉化合物在不对称合成和药物发现中起着极其重要的作用。在此，使用芳基腈或含氰基化合物和手性 β-氨基醇作为起始原料，开发了一种更简单、更环保、更有效的微波辅助快速获得手性恶唑啉的方案。在浓缩溶液或无溶剂条件下，在可回收多相催化剂存在下，反应顺利进行。该方法具有快速、简便、环保、原子经济性高、收率高等优点。该协议将来应该在社区中得到更广泛的应用。
• 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。
• Superacid catalyzed ring-opening reactions involving 2-oxazolines and the role of superelectrophilic intermediates
  作者：Douglas A. Klumpp、Rendy Rendy、Aaron McElrea

  DOI：10.1016/j.tetlet.2004.08.109

  日期：2004.10

  A variety of 2-oxazolines are found to react with arenes in superacidic triflic acid, CF3SO3H. It is proposed that the 2-oxazolines are protonated twice in triflic acid and the resulting intermediates undergo ring-opening reactions to produce reactive, dicationic species. These superelectrophiles are capable of reacting with benzene and o-dichlorobenzene in high yields by Friedel-Crafts type reactions. (C) 2004 Elsevier Ltd. All rights reserved.
• Study on the tandem synthesis of optically active 2-substituted 4 (or 5)-phenyl-1,3-oxazolines
  作者：Haizhen Jiang、Wenjun Lu、Yeshan Cai、Wen Wan、Shaoxiong Wu、Shizheng Zhu、Jian Hao

  DOI：10.1016/j.tet.2012.12.078

  日期：2013.3

  Optically active (S)-2-aryl-4 (or 5)-phenyl-1,3-oxazolines and (S)-2-fluoroalkyl-4-phenyl-1,3-oxazolines were synthesized from a tandem one-pot reaction of (S)-2-amino-2-phenylethanol with a corresponding carboxylic acid in toluene at 90 degrees C in the presence of PPh3/CBr4 and excess Et3N. The use of aromatic carboxylic acids were determined to proceed through N-(2-bromo-1-phenyl-ethyl)-arylamides 5 and N-aroyl aziridine intermediates 6, which resulted in the formation of (S)-2-aryl-4-phenyl-1,3-oxazolines and (S)-2-aryl-5-phenyl-1,3-oxazolines, respectively. Concurrently, the reaction with fluorinated aliphatic carboxylic acid substrates proceeded via N-(2-hydroxy-1-phenyl-ethyl)-fluoroalkyl amide intermediates 8, which were converted into N-(2-bromo-1-phenyl-ethyl)-fluoroalkyl amide intermediates 9, and then into (S)-2-fluoroalkyl-4-phenyl-1,3-oxazolines as final products. Reaction mechanisms that mainly passed through the formation of aziridine intermediates 6 in the reaction with aromatic carboxylic acids and the formation of fluoroalkyl amide intermediates 8 and 9 in the reaction with fluorinated aliphatic carboxylic acid were proposed. The acidities of the carboxylic acids that were employed were found to play a key role in the selective formation of various intermediates during this reaction. (c) 2013 Elsevier Ltd. All rights reserved.