(2S)-(-)-2-[(butyryloxy)methyl]-1-dodecanoylaziridine | 192506-22-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-(-)-2-[(butyryloxy)methyl]-1-dodecanoylaziridine
• 英文别名: [(2S)-1-dodecanoylaziridin-2-yl]methyl butanoate
• CAS: 192506-22-2
• 化学式: C₁₉H₃₅NO₃
• 分子量: 325.492
• InChiKey: AIWKIMKRCGWTIM-DIMJTDRSSA-N

物化性质

• 沸点：
  436.2±18.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-(-)-2-[(butyryloxy)methyl]-1-dodecanoylaziridine 在 palladium on activated charcoal Dowex 50Wx₂ (sodium form) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 disodium (2R)-3-(butyryloxy)-2-(dodecanoylamino)propan-1-yl phosphate
  参考文献：
  名称：

  Aziridines as Precursors for Chiral Amide-Containing Surfactants

  摘要：

  Optically active aziridines can be used as precursors in the synthesis of several enantiopure amide-containing surfactants. Acylation of the aziridines is a convenient method for both the activation of the aziridine ring and the introduction of the hydrocarbon chain. The regioselectivity of the ring-opening reactions using dibenzyl phosphate could be controlled by varying the reaction temperature. In this way both regioisomers of the phospholipid analogues could be obtained. In the course of these experiments, an unprecedented rearrangement of a-acylamino phosphotriesters was observed. A mechanism for this group exchange reaction was proposed based on the compared reactivities of related compounds and FT-IR spectroscopic data Application of high pressures (12 kBar) for the ring opening of the activated aziridines with imidazole led to the efficient formation of the desired surfactant with complete regioselectivity.

  DOI：

  10.1021/jo962298a
• 作为产物：
  描述：

  (R)-(-)-丁酸缩水甘油酯 在 ammonium sulfate 、 sodium azide 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (2S)-(-)-2-[(butyryloxy)methyl]-1-dodecanoylaziridine
  参考文献：
  名称：

  Aziridines as Precursors for Chiral Amide-Containing Surfactants

  摘要：

  Optically active aziridines can be used as precursors in the synthesis of several enantiopure amide-containing surfactants. Acylation of the aziridines is a convenient method for both the activation of the aziridine ring and the introduction of the hydrocarbon chain. The regioselectivity of the ring-opening reactions using dibenzyl phosphate could be controlled by varying the reaction temperature. In this way both regioisomers of the phospholipid analogues could be obtained. In the course of these experiments, an unprecedented rearrangement of a-acylamino phosphotriesters was observed. A mechanism for this group exchange reaction was proposed based on the compared reactivities of related compounds and FT-IR spectroscopic data Application of high pressures (12 kBar) for the ring opening of the activated aziridines with imidazole led to the efficient formation of the desired surfactant with complete regioselectivity.

  DOI：

  10.1021/jo962298a

文献信息

• Aziridines as Precursors for Chiral Amide-Containing Surfactants
  作者：N. A. J. M. Sommerdijk、P. J. J. A. Buynsters、H. Akdemir、D. G. Geurts、R. J. M. Nolte、B. Zwanenburg

  DOI：10.1021/jo962298a

  日期：1997.7.1

  Optically active aziridines can be used as precursors in the synthesis of several enantiopure amide-containing surfactants. Acylation of the aziridines is a convenient method for both the activation of the aziridine ring and the introduction of the hydrocarbon chain. The regioselectivity of the ring-opening reactions using dibenzyl phosphate could be controlled by varying the reaction temperature. In this way both regioisomers of the phospholipid analogues could be obtained. In the course of these experiments, an unprecedented rearrangement of a-acylamino phosphotriesters was observed. A mechanism for this group exchange reaction was proposed based on the compared reactivities of related compounds and FT-IR spectroscopic data Application of high pressures (12 kBar) for the ring opening of the activated aziridines with imidazole led to the efficient formation of the desired surfactant with complete regioselectivity.