N-[(S)-α-phenylethyl]aziridin-2(S)-yl-methanol | 216597-58-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[(S)-α-phenylethyl]aziridin-2(S)-yl-methanol
• 英文别名: (2S)-N-[(1S)-phenylethyl]-2-hydroxymethyl Aziridine；[(2S)-1-[(1S)-1-phenylethyl]aziridin-2-yl]methanol
• CAS: 216597-58-9
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: BMEHDCBKAUDFBH-HFLPBZFISA-N

物化性质

• 沸点：
  240.6±15.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(S)-α-phenylethyl]aziridin-2(S)-yl-methanol 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 28.0h， 生成 3-benzyloxy-2(R)-((S)-α-methylbenzylamino)propyl acetate
  参考文献：
  名称：

  Preparation of Both (D)- and (L)-Serinol Derivatives from N-[(S)-a-Methylbenzyl]-aziridine-2(S)-methanol

  摘要：

  DOI：

  10.3987/com-98-8129
• 作为产物：
  描述：

  methyl 1-(1S-phenylethyl)-aziridine-2S-carboxylate 在 sodium tetrahydroborate 、 lithium chloride 作用下， 反应 16.0h， 以87%的产率得到N-[(S)-α-phenylethyl]aziridin-2(S)-yl-methanol
  参考文献：
  名称：

  Synthesis of four enantiomers of 2-acetamido-1-hydroxypropylphosphonates

  摘要：

  Enantiomerically pure diethyl 2-acetamido-1-hydroxypropylphosphonates were synthesised from N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes via phosphonylation followed by acetylation of the hydroxy groups and the simultaneous hydrogenolytic cleavage of the aziridine rings and the removal of the chiral auxiliaries. In addition, enantiomerically pure diethyl (1S,2R)- and (1R,2S)-2-amino-1-hydroxypropylphosphonates (the phosphonate analogues of isothreonine) were separated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.021

文献信息

• Synthesis of Substituted-(<i>l</i>)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol
  作者：Do Kyu Pyun、Cheol Hae Lee、Hyun-Joon Ha、Chan Sun Park、Jae-Won Chang、Won Koo Lee

  DOI：10.1021/ol016861+

  日期：2001.12.1

  [GRAPHICS]Enantiomerically pure (l)-tryptophanol (5) was synthesized from 4(R)-iodomethyl-2-oxazolidinone (2) and indolylmagnesium bromide in three steps (52% overall yield). Using this procedure, we also prepared various tryptophanols with substituent(s) on the indole ring. Furthermore, optically active 4(R)-iodomethyl-2-oxazolidinone was readily prepared from an enantiomerically pure aziridine-2(S)-methanol in high yield.
• Synthesis of four enantiomers of 2-acetamido-1-hydroxypropylphosphonates
  作者：Andrzej E. Wróblewski、Joanna Drozd

  DOI：10.1016/j.tetasy.2007.04.021

  日期：2007.5

  Enantiomerically pure diethyl 2-acetamido-1-hydroxypropylphosphonates were synthesised from N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes via phosphonylation followed by acetylation of the hydroxy groups and the simultaneous hydrogenolytic cleavage of the aziridine rings and the removal of the chiral auxiliaries. In addition, enantiomerically pure diethyl (1S,2R)- and (1R,2S)-2-amino-1-hydroxypropylphosphonates (the phosphonate analogues of isothreonine) were separated. (C) 2007 Elsevier Ltd. All rights reserved.
• Preparation of Both (D)- and (L)-Serinol Derivatives from N-[(S)-a-Methylbenzyl]-aziridine-2(S)-methanol
  作者：Won Koo Lee、Soo-Kyung Choi

  DOI：10.3987/com-98-8129

  日期：——