[1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester | 565430-72-0

• 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-diazo-2-oxo-propyl]-carbamic acid tert-butylester
• 英文别名: (R)-[1-(4-tert-butoxybenzyl)-3-diazo-2-oxopropyl]carbamic acid t-butyl ester
• CAS: 565430-72-0
• 化学式: C₁₉H₂₇N₃O₄
• 分子量: 361.441
• InChiKey: YFGGFFWOPKRXEW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  101.03
• 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-diazo-2-oxo-propyl]-carbamic acid tert-butylester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) silver benzoate 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.75h， 生成 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl 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
• 作为产物：
  描述：

  重氮甲烷 、 N-[叔丁氧羰基]-O-(叔丁基)-D-酪氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.83h， 生成 [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester
  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