[1-(4-tert-butoxy-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester | 565430-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-(4-tert-butoxy-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester
• 英文别名: (R)-[1-(4-tert-butoxybenzyl)-3-oxopropyl]carbamic acid tert-butyl ester
• CAS: 565430-83-3
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: UEHOCESLBJJWMX-HNNXBMFYSA-N

物化性质

• 沸点：
  471.0±45.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [1-(4-tert-butoxy-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enoic acid
  参考文献：
  名称：

  Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols

  摘要：

  [GRAPHICS]Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.

  DOI：

  10.1021/ol027237f
• 作为产物：
  描述：

  (R)-3-tert-Butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 [1-(4-tert-butoxy-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols

  摘要：

  [GRAPHICS]Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.

  DOI：

  10.1021/ol027237f