(S)-trans-N-(2-hydroxy-1-phenylethyl)-2,4-dimethoxycinnamamide | 1176919-41-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-trans-N-(2-hydroxy-1-phenylethyl)-2,4-dimethoxycinnamamide
• 英文别名: (E)-3-(2,4-dimethoxyphenyl)-N-[(1S)-2-hydroxy-1-phenylethyl]prop-2-enamide
• CAS: 1176919-41-7
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: XPOISVZVSVXTBP-QXLXQBSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-trans-N-(2-hydroxy-1-phenylethyl)-2,4-dimethoxycinnamamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(+)-(S)-trans-2-(2,4-dimethoxyphenyl)-(4-phenyloxazoline-2-yl)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
• 作为产物：
  描述：

  L-苯甘氨醇 、 (E)-3-(2,4-dimethoxyphenyl)prop-2-enoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以81%的产率得到(S)-trans-N-(2-hydroxy-1-phenylethyl)-2,4-dimethoxycinnamamide
  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

文献信息

• Arylid-OX and Arylid-BOX derived catalysts: applications in catalytic asymmetric cyclopropanation
  作者：Elisabete Palma Carreiro、Anthony J. Burke、J.P. Prates Ramalho、Ana Isabel Rodrigues

  DOI：10.1016/j.tetasy.2009.04.005

  日期：2009.6

  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.