(S,E)-4-benzyl-2-styryl-4,5-dihydrooxazoline | 1280542-81-5

• 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,E)-4-benzyl-2-styryl-4,5-dihydrooxazoline
• 英文别名: (S,E)-4-benzyl-2-styryl-4,5-dihydrooxazole；(4S)-4-benzyl-2-cinnamoyl-2-oxazoline；(4S)-4-benzyl-2-[(E)-2-phenylethenyl]-4,5-dihydro-1,3-oxazole
• CAS: 1280542-81-5
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: KXBUEGYIGCYJIV-FLVLSHQESA-N

物化性质

• 熔点：
  71-73 °C
• 沸点：
  381.1±21.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-(2-diethoxyphosphoryl)acetamide-3-phenylpropanol 在 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 (S,E)-4-benzyl-2-styryl-4,5-dihydrooxazoline
  参考文献：
  名称：

  Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides

  摘要：

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.003

文献信息

• Palladium-Catalyzed C-2 C–H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands
  作者：Tuo Xi、Yuncai Mei、Zhan Lu

  DOI：10.1021/acs.orglett.5b03041

  日期：2015.12.18

  A direct, efficient, and practical protocol to install a chiral Oxazoline unit onto aryl/heteroaryl rings via palladium-catalyzed C-H functionalization of 2-positions of oXazolines with a variety of halides using dppe as the ligand has been developed. Various chiral oxazdline ligands could be synthesized, even in a 10-g scale process. This protocol is a good supplement to traditional methods and for diverse synthesis of chiral oxazoline ligands.