4-[5-(4-benzyloxyphenyl)-4-pentenyl]-1-(tert-butoxycarbonyl)piperidine | 859140-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[5-(4-benzyloxyphenyl)-4-pentenyl]-1-(tert-butoxycarbonyl)piperidine
• CAS: 859140-07-1
• 化学式: C₂₈H₃₇NO₃
• 分子量: 435.607
• InChiKey: QNVAIODPUTYMNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[5-(4-benzyloxyphenyl)-4-pentenyl]-1-(tert-butoxycarbonyl)piperidine 在 palladium on activated charcoal 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 216.0h， 生成 1-(tert-butoxycarbonyl)-4-[5-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]pentyl]piperidine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006
• 作为产物：
  描述：

  [(4-benzyloxy)benzyl]triphenylphosphonium chloride 、 tert-butyl 4-(4-oxobutyl)piperidine-1-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以76%的产率得到4-[5-(4-benzyloxyphenyl)-4-pentenyl]-1-(tert-butoxycarbonyl)piperidine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006