(1S,2S,4R)-1-methyl-2-[(2S)-2-propan-2-ylaziridin-1-yl]-4-prop-1-en-2-ylcyclohexan-1-ol | 1564287-63-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,4R)-1-methyl-2-[(2S)-2-propan-2-ylaziridin-1-yl]-4-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 1564287-63-3
• 化学式: C₁₅H₂₇NO
• 分子量: 237.385
• InChiKey: NRQBDRLBDYYGMI-WHWZVRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  (4R)-limonene 1,2-epoxide 、 (S)-2-isopropylaziridine 在 三乙胺 作用下， 以 水 为溶剂， 反应 24.0h， 以83%的产率得到(1S,2S,4R)-1-methyl-2-[(2S)-2-propan-2-ylaziridin-1-yl]-4-prop-1-en-2-ylcyclohexan-1-ol
  参考文献：
  名称：

  Limonene oxide derived aziridinyl alcohols as highly efficient catalysts for asymmetric additions of organozinc species to aldehydes

  摘要：

  The facile synthesis of a series of novel catalysts bearing a tertiary hydroxyl group and an aziridine moiety as chelating centers constructed on the scaffold derived from limonene oxide is described. The newly prepared compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, affording the corresponding chiral alcohols in very high chemical yields (up to 96%) and with excellent ee's of ca. 95%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.011
• 作为试剂：
  描述：

  diethylzinc 、 2-甲基苯甲醛 在 (1S,2S,4R)-1-methyl-2-[(2S)-2-propan-2-ylaziridin-1-yl]-4-prop-1-en-2-ylcyclohexan-1-ol 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.5h， 以92%的产率得到(R)-1-o-tolyl-propan-1-ol
  参考文献：
  名称：

  Limonene oxide derived aziridinyl alcohols as highly efficient catalysts for asymmetric additions of organozinc species to aldehydes

  摘要：

  The facile synthesis of a series of novel catalysts bearing a tertiary hydroxyl group and an aziridine moiety as chelating centers constructed on the scaffold derived from limonene oxide is described. The newly prepared compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, affording the corresponding chiral alcohols in very high chemical yields (up to 96%) and with excellent ee's of ca. 95%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.011

文献信息

• Limonene oxide derived aziridinyl alcohols as highly efficient catalysts for asymmetric additions of organozinc species to aldehydes
  作者：Michał Rachwalski

  DOI：10.1016/j.tetasy.2013.11.011

  日期：2014.2

  The facile synthesis of a series of novel catalysts bearing a tertiary hydroxyl group and an aziridine moiety as chelating centers constructed on the scaffold derived from limonene oxide is described. The newly prepared compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, affording the corresponding chiral alcohols in very high chemical yields (up to 96%) and with excellent ee's of ca. 95%. (C) 2013 Elsevier Ltd. All rights reserved.