3'-(3-Hydroxy-propyl)-biphenyl-3-carboxylic acid methyl ester

• 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: 3'-(3-Hydroxy-propyl)-biphenyl-3-carboxylic acid methyl ester
• 英文别名: Methyl 3-[3-(3-hydroxypropyl)phenyl]benzoate
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: NOWMCLYSDDDTRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-(3-Hydroxy-propyl)-biphenyl-3-carboxylic acid methyl ester 在 palladium on activated charcoal 吡啶 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 、 对甲苯磺酰氯 、 lithium hexamethyldisilazane 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3'-[2-((2S,3S)-4-Oxo-3-trityloxymethyl-oxetan-2-yl)-ethyl]-biphenyl-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Activities of New HMG-CoA Synthase Inhibitors: 2-Oxetanones with a Side Chain Containing Biphenyl, Terphenyl or Phenylpyridine

  摘要：

  A series of 1233A analogs containing biphenylyl, terphenylyl or phenylpyridyl groups in their side chain were synthesized and tested for the inhibitory activities against 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase and inhibition for the cholesterol biosynthesis in the mouse liver. The compounds with an oxetane, cyclobutanone or gamma-butyrolactone ring as isosters of a 2-oxetanone ring were entirely inactive. Among sythetic analogs, anti-4-[3-[2-(5-isopropyl-2-pyridyl)-ethyl]-phenyl]ethyl]-3-hydroxymethyl-2-oxetanone (10b) was most active in vitro. The structure-activity relationships on the transformations of 2-oxetanone and its side chain were obtained.

  DOI：

  10.3987/com-94-6720