1,2-bis(benzyloxy)-4-<1-hydroxy-2-ethyl>benzene | 95484-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,2-bis(benzyloxy)-4-<1-hydroxy-2-ethyl>benzene
• CAS: 95484-12-1
• 化学式: C₄₀H₃₈N₂O₅
• 分子量: 626.752
• InChiKey: UGNGPNPVULYTLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.31
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(benzyloxy)-4-<1-hydroxy-2-ethyl>benzene 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives

  摘要：

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.

  DOI：

  10.1021/jm50001a017
• 作为产物：
  描述：

  3,4-bis(benzyloxy)-α-acetophenone 在 aluminum isopropoxide 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 以45%的产率得到1,2-bis(benzyloxy)-4-<1-hydroxy-2-ethyl>benzene
  参考文献：
  名称：

  Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives

  摘要：

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.

  DOI：

  10.1021/jm50001a017