1-(2-azidoethyl)-N-[(3S)-2-oxooxolan-3-yl]cyclopentane-1-carboxamide | 289913-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2-azidoethyl)-N-[(3S)-2-oxooxolan-3-yl]cyclopentane-1-carboxamide
• CAS: 289913-56-0
• 化学式: C₁₂H₁₈N₄O₃
• 分子量: 266.3
• InChiKey: JQNHTDFKHMZUMZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-azidoethyl)-N-[(3S)-2-oxooxolan-3-yl]cyclopentane-1-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 {2-[1-((S)-2-Oxo-tetrahydro-furan-3-ylcarbamoyl)-cyclopentyl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Cyclic thioether peptide mimetics as VCAM–VLA-4 antagonists

  摘要：

  Selective substitution of a sulfur atom by carbon in a highly potent 13-membered cyclic disulfide was accomplished by intramolecular displacement of a bromide. The potency of the resulting thioethers in the VCAM/VLA-4 assay was dependant on rin size and the position of the sulfur atom. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00175-x
• 作为产物：
  描述：

  3-氨基二氢-2(3H)-呋喃酮盐酸盐(1:1) 、 1-(2-azido-ethyl)-cyclopentanecarboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到1-(2-azidoethyl)-N-[(3S)-2-oxooxolan-3-yl]cyclopentane-1-carboxamide
  参考文献：
  名称：

  Cyclic thioether peptide mimetics as VCAM–VLA-4 antagonists

  摘要：

  Selective substitution of a sulfur atom by carbon in a highly potent 13-membered cyclic disulfide was accomplished by intramolecular displacement of a bromide. The potency of the resulting thioethers in the VCAM/VLA-4 assay was dependant on rin size and the position of the sulfur atom. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00175-x

文献信息

• Cyclic thioether peptide mimetics as VCAM–VLA-4 antagonists
  作者：Nader Fotouhi、Pramod Joshi、Jefferson W. Tilley、Karen Rowan、Virginia Schwinge、Barry Wolitzky

  DOI：10.1016/s0960-894x(00)00175-x

  日期：2000.6

  Selective substitution of a sulfur atom by carbon in a highly potent 13-membered cyclic disulfide was accomplished by intramolecular displacement of a bromide. The potency of the resulting thioethers in the VCAM/VLA-4 assay was dependant on rin size and the position of the sulfur atom. (C) 2000 Elsevier Science Ltd. All rights reserved.