(S)-2-(2,2-dimethylaziridin-1-yl)-1-phenylethanol | 1442646-87-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(2,2-dimethylaziridin-1-yl)-1-phenylethanol
• 英文别名: (1S)-2-(2,2-dimethylaziridin-1-yl)-1-phenylethanol
• CAS: 1442646-87-8
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: VGHUZFCLIMSZLR-JTDNENJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(+)-α-乙酰氧基苯乙酸 在 草酰氯 、 三乙氧基硅烷 、 zinc diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 (S)-2-(2,2-dimethylaziridin-1-yl)-1-phenylethanol
  参考文献：
  名称：

  Mandelic acid derived α-aziridinyl alcohols as highly efficient ligands for asymmetric additions of zinc organyls to aldehydes

  摘要：

  A straightforward synthesis of a series of new catalysts containing secondary hydroxyl and aziridine moieties as nucleophilic centers built on the chiral scaffold of (S)-(+)-mandelic acid is described. The new compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, which yielded the corresponding chiral alcohols in high chemical yields (up to 95%) and with excellent ee's of ca. 90%. The strong influence of the stereogenic center located at the aziridine subunit on the stereochemical outcome is also reported on. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.019
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 (S)-2-(2,2-dimethylaziridin-1-yl)-1-phenylethanol 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 30.0h， 以42%的产率得到
  参考文献：
  名称：

  Mandelic acid derived α-aziridinyl alcohols as highly efficient ligands for asymmetric additions of zinc organyls to aldehydes

  摘要：

  A straightforward synthesis of a series of new catalysts containing secondary hydroxyl and aziridine moieties as nucleophilic centers built on the chiral scaffold of (S)-(+)-mandelic acid is described. The new compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, which yielded the corresponding chiral alcohols in high chemical yields (up to 95%) and with excellent ee's of ca. 90%. The strong influence of the stereogenic center located at the aziridine subunit on the stereochemical outcome is also reported on. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.019

文献信息

• Mandelic acid derived α-aziridinyl alcohols as highly efficient ligands for asymmetric additions of zinc organyls to aldehydes
  作者：Michał Rachwalski、Szymon Jarzyński、Marcin Jasiński、Stanisław Leśniak

  DOI：10.1016/j.tetasy.2013.04.019

  日期：2013.6

  A straightforward synthesis of a series of new catalysts containing secondary hydroxyl and aziridine moieties as nucleophilic centers built on the chiral scaffold of (S)-(+)-mandelic acid is described. The new compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, which yielded the corresponding chiral alcohols in high chemical yields (up to 95%) and with excellent ee's of ca. 90%. The strong influence of the stereogenic center located at the aziridine subunit on the stereochemical outcome is also reported on. (C) 2013 Elsevier Ltd. All rights reserved.