3-[3,4-bis(benzyloxy)phenyl]prop-1-ene | 857579-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[3,4-bis(benzyloxy)phenyl]prop-1-ene
• 英文别名: 4-allyl-1,2-bis-benzyloxy-benzene；4-Allyl-1,2-bis-benzyloxy-benzol；3.4-Dibenzyloxy-1-allyl-benzol；1,2-Bis(phenylmethoxy)-4-prop-2-enylbenzene；1,2-bis(phenylmethoxy)-4-prop-2-enylbenzene
• CAS: 857579-67-0
• 化学式: C₂₃H₂₂O₂
• 分子量: 330.426
• InChiKey: FWTZWNLPTWLHBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[3,4-bis(benzyloxy)phenyl]prop-1-ene 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 以76%的产率得到3-(3,4-bis(benzyloxy)phenyl)propan-1-ol
  参考文献：
  名称：

  Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

  摘要：

  Starting from the beta-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gas, while they only show weak or even no beta-arrestin-2 recruitment at both beta(1)- and beta(2)-AR Molecular dynamics simulations suggest that the difference in G protein efficacy and beta-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the beta(2)-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser(5.46) and Asn(6.55), and the aromatic head group of the ligands.

  DOI：

  10.1021/acs.jmedchem.9b00349
• 作为产物：
  描述：

  甲基丁香酚 在 乙醚 、 potassium carbonate 、 丙酮 、 xylene 作用下， 生成 3-[3,4-bis(benzyloxy)phenyl]prop-1-ene
  参考文献：
  名称：

  Schoepf et al., Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 30,58

  摘要：

  DOI：

文献信息

• Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias
  作者：Markus Stanek、Louis-Philippe Picard、Maximilian F. Schmidt、Jonas M. Kaindl、Harald Hübner、Michel Bouvier、Dorothée Weikert、Peter Gmeiner

  DOI：10.1021/acs.jmedchem.9b00349

  日期：2019.5.23

  Starting from the beta-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gas, while they only show weak or even no beta-arrestin-2 recruitment at both beta(1)- and beta(2)-AR Molecular dynamics simulations suggest that the difference in G protein efficacy and beta-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the beta(2)-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser(5.46) and Asn(6.55), and the aromatic head group of the ligands.
• Schoepf et al., Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 30,58
  作者：Schoepf et al.

  DOI：——

  日期：——