(+)-bis[(S)-4-phenyloxazoline-2-yl]-2-(2-methoxyphenyl)ethene | 1176919-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+)-bis[(S)-4-phenyloxazoline-2-yl]-2-(2-methoxyphenyl)ethene
• CAS: 1176919-48-4
• 化学式: C₂₇H₂₄N₂O₃
• 分子量: 424.499
• InChiKey: OFWISLGKFRQUSD-DNQXCXABSA-N

物化性质

• 沸点：
  558.9±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.41
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (S,S)-N,N'-bis(2-hydroxy-1-phenylethyl)-2-(2-methoxybenzylidene)malonamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(+)-bis[(S)-4-phenyloxazoline-2-yl]-2-(2-methoxyphenyl)ethene
  参考文献：
  名称：

  Arylid-OX and Arylid-BOX derived catalysts: applications in catalytic asymmetric cyclopropanation

  摘要：

  A novel family of chiral non-racemic monodentate oxazoline ligands known as Arylid-OXs 1a and 1b was prepared in good overall yields. These ligands were screened in bench-mark Cu(I)-catalyzed cyclopropanations and gave ees as high as 58%. Both H-1 NMR and computational studies using 1a indicated that the active catalyst was most likely to be the di-coordinated complex, Cu(I)-1a(2)(MeCN)(2). Two novel ortho-substituted Arylid-BOX ligands 2a and 2b were also synthesized in very good yields. These ligands were tested in the same reaction as for 1a and 1b and, although excellent yields could be obtained with 2b, which is assumed to be due to an electron-donating effect from the ortho-methoxy group, a best ee of only 56% was obtained with 2a. In fact, both the enantioselectivities and diastereoselectivities obtained with these ortho-substituted ligands were in line with those previously obtained with the para-substituted series. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.005