(S)-4-azidobutan-1,2-diol | 661462-06-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-4-azidobutan-1,2-diol
• 英文别名: (-)-(2S)-4-azidobutane-1,2-diol；(2S)-4-azidobutane-1,2-diol
• CAS: 661462-06-2
• 化学式: C₄H₉N₃O₂
• 分子量: 131.134
• InChiKey: CBRREUPPRHQWCX-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (S)-4-azidobutan-1,2-diol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以93%的产率得到(S)-4-azido-1-tert-butyldimethylsilyloxybutan-2-ol
  参考文献：
  名称：

  溴肟的两种对映异构体的合成及其绝对构型的测定

  摘要：

  Brevioxime 是一种保幼激素生物合成的抑制剂，从 Penicillium brevicompactum 中分离出来。我们合成了短缩肟的两种对映异构体，并确定了天然产物的绝对构型为 S。

  DOI：

  10.3987/com-03-s64
• 作为产物：
  描述：

  (4S)-4-(2-azidoethyl)-2-tert-butyl-1,3-dioxolane 在 Amberlyst 15 acidic form 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到(S)-4-azidobutan-1,2-diol
  参考文献：
  名称：

  Structure–affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol

  摘要：

  The synthesis and NMDA receptor affinity of ring and side-chain homologues of etoxadrol and dexoxadrol are described. For the regioselective synthesis of etoxadrol homologues, the regioisomeric 4-azidobutanediols (+/-)-9 and (+/-)-14 were employed. A synthesis of the enantiomerically pure azidobutanediols (S)-, (R)-9 and (S)-, (R)-14 was developed and the homochiral building blocks were used for the synthesis of enantiomerically pure etoxadrol and dexoxadrol homologues. The affinity of the racemic and enantiomerically pure primary amines toward the phencyclidine binding site of the NMDA receptor was investigated in receptor binding studies with tritium labeled [H-3]-(+)-MK-801 as radioligand. Benzaldehyde derivatives (+/-)-12a, (+/-)-13a, and (+/-)-16a bearing a proton at the acetalic position do not interact significantly with the NMDA receptor. An enantioselective NMDA receptor binding was observed for the trans-configured 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)ethanamine 13b, the (2-ethyl-2-phenyl-1,3-dioxan-4-yl)methanamine 16b, and the (2,2-diphenyl-1,3-dioxan-4-yl)methanamine 16c. The NMDA receptor affinity of these compounds resides almost exclusively in the (S)-configured enantiomers (2S,4S)-13b, (2S,4S)-16b, and (4S)-16c. The lowest K-i-value in this series was found for the (2S,4S)-configured 1,3-dioxolane (2S,4S)-13b (K-i = 69 nM), which is in the range of the Ki-value of the lead compounds etoxadrol and dexoxadrol, indicating that the 2-aminoethyl and the piperidin-2-yl substituents lead to similar NMDA receptor interactions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.030