2-[3-(benzyloxy)phenyl]-1,3-propanediol | 155440-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[3-(benzyloxy)phenyl]-1,3-propanediol
• 英文别名: 2-(3-benzyloxyphenyl)propane-1,3-diol；2-(3-Phenylmethoxyphenyl)propane-1,3-diol
• CAS: 155440-95-2
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: SIFMNKWCPLMJIK-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  455.4±40.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3-(benzyloxy)phenyl]-1,3-propanediol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.5h， 生成
  参考文献：
  名称：

  2-Benzyl and 2-phenyl-3-hydroxypropyl pivalates as protein kinase C ligands

  摘要：

  A series of 2-benzyl and 2-phenyl-3-hydroxypropyl pivalates designed to incorporate the principal pharmacophores of phorbol esters have been synthesized and tested as PKC-alpha ligands. Among the analogues, 13c exhibited the most potent binding affinity with a K-i = 0.7 mu M. The synthesized analogues were subjected to molecular modeling analysis based on two alternative models of the phorbol pharmacophore and a docking study or 13c was carried out. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.051
• 作为产物：
  描述：

  3-羟基苯甲醇 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.0h， 生成 2-[3-(benzyloxy)phenyl]-1,3-propanediol
  参考文献：
  名称：

  2-Benzyl and 2-phenyl-3-hydroxypropyl pivalates as protein kinase C ligands

  摘要：

  A series of 2-benzyl and 2-phenyl-3-hydroxypropyl pivalates designed to incorporate the principal pharmacophores of phorbol esters have been synthesized and tested as PKC-alpha ligands. Among the analogues, 13c exhibited the most potent binding affinity with a K-i = 0.7 mu M. The synthesized analogues were subjected to molecular modeling analysis based on two alternative models of the phorbol pharmacophore and a docking study or 13c was carried out. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.051

文献信息

• Enzymatic asymmetrization of some prochiral and meso diols through monoacetylation with pig pancreatic lipase (PPL)
  作者：Giuseppe Guanti、Luca Banfi、Renata Riva

  DOI：10.1016/s0957-4166(00)80471-1

  日期：1994.1

  Monoacetates 1-8 and 10-11, derived from asymmetric monoesterification of prochiral or meso diols, have been obtained in good to excellent enantiomeric excess by using inexpensive crude PPL supported on celite, and vinyl acetate as both solvent and acylating agent. Under these conditions reactions are fast and reproducible, and the enzyme can be recycled.
• Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation
  作者：Stefanie Keil、Marco Müller、Gerhard Zoller、Guido Haschke、Katrin Schroeter、Maike Glien、Sven Ruf、Ingo Focken、Andreas W. Herling、Dieter Schmoll

  DOI：10.1021/jm101179e

  日期：2010.12.23

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.