[1-(4-tert-butoxy-benzyl)-3-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester | 507276-84-8

• 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-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,4S)-4-hydroxy-1-[4-[(2-methylpropan-2-yl)oxy]phenyl]hex-5-en-2-yl]carbamate
• CAS: 507276-84-8
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: MQRIHQRPTRSBIG-DLBZAZTESA-N

物化性质

• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(4-tert-butoxy-benzyl)-3-hydroxy-pent-4-enyl]-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 3.0h， 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：

  Boc-O-叔丁基-L-酪氨酸 在 N-甲基吗啉 、 silver benzoate 、 二异丁基氢化铝 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.58h， 生成 [1-(4-tert-butoxy-benzyl)-3-hydroxy-pent-4-enyl]-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

文献信息

• Mu opioid receptor ligands: methods of use and synthesis
  申请人：Harrison Bryce A.

  公开号：US20090093534A1

  公开（公告）日：2009-04-09

  Novel compounds and compositions including those compounds, as well as methods of using and making the compounds are herein described. The compounds are useful in therapeutic applications, including modulation of disease or disease symptoms in a subject (e.g., mammal, human, dog, cat, horse). The compounds are useful as modulators of the mu opioid receptor (MOR) through their binding affinity with that receptor.

  本文描述了包括这些化合物在内的新型化合物和组合物，以及使用和制造这些化合物的方法。这些化合物在治疗应用中有用，包括调节受试者（例如哺乳动物、人类、狗、猫、马）的疾病或疾病症状。这些化合物通过它们与μ阿片受体（MOR）的结合亲和力作为MOR的调节剂是有用的。
• US7223888B2
  申请人：——

  公开号：US7223888B2

  公开（公告）日：2007-05-29
• US7759514B2
  申请人：——

  公开号：US7759514B2

  公开（公告）日：2010-07-20
• Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols
  作者：Zhangjie Shi、Bryce A. Harrison、Gregory L. Verdine

  DOI：10.1021/ol027237f

  日期：2003.3.1

  [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.