3-<2-(3-biphenylyl)ethyl>cyclobutanone | 158503-23-2

• 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-<2-(3-biphenylyl)ethyl>cyclobutanone
• 英文别名: 3-[2-(3-Phenylphenyl)ethyl]cyclobutan-1-one
• CAS: 158503-23-2
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: HPIUUNCLVCMHOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-<2-(3-biphenylyl)ethyl>cyclobutanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以91%的产率得到3-<2-(3-biphenylyl)ethyl>butyrolactone
  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
• 作为产物：
  描述：

  4-(3-biphenylyl)-1-butene 在 溶剂黄146 、 锌 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 3-<2-(3-biphenylyl)ethyl>cyclobutanone
  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

文献信息

• Synthesis and Biological Activities of New HMG-CoA Synthase Inhibitors: 2-Oxetanones with a Side Chain Containing Biphenyl, Terphenyl or Phenylpyridine
  作者：Hirokazu Hashizume、Hajime Ito、Naoaki Kanaya、Hajime Nagashima、Hiroyuki Usui、Reiko Oshima、Munefumi Kanao、Hiroshi Tomoda、Toshiaki Sunazuka、Tohru Nagamitsu、Hidetoshi Kumagai、Satoshi Omura

  DOI：10.3987/com-94-6720

  日期：——

  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.