(4R)-4-(2-azidoethyl)-2-tert-butyl-1,3-dioxolane | 872104-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (4R)-4-(2-azidoethyl)-2-tert-butyl-1,3-dioxolane
• CAS: 872104-54-6
• 化学式: C₉H₁₇N₃O₂
• 分子量: 199.253
• InChiKey: JTOLGBGHOWLGIL-GVHYBUMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.22
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R)-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(+)-(2R)-4-azidobutane-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
• 作为产物：
  描述：

  (4R)-2-(2-tert-butyl-1,3-dioxolan-4-yl)ethan-1-ol 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 (4R)-4-(2-azidoethyl)-2-tert-butyl-1,3-dioxolane
  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