ethyl 3-[3-(4-fluorophenoxy)phenyl]prop-2-enoate | 188953-45-9

• 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: ethyl 3-[3-(4-fluorophenoxy)phenyl]prop-2-enoate
• CAS: 188953-45-9
• 化学式: C₁₇H₁₅FO₃
• 分子量: 286.303
• InChiKey: STWHQKPEDUVVIW-UHFFFAOYSA-N

物化性质

• 沸点：
  393.1±32.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-[3-(4-fluorophenoxy)phenyl]prop-2-enoate 在 氢气 、 镍 作用下， 以 甲醇 为溶剂， 生成 Ethyl 3-[3-(4-fluorophenoxy)phenyl]propanoate
  参考文献：
  名称：

  Phosphonosulfonates Are Potent, Selective Inhibitors of Dehydrosqualene Synthase and Staphyloxanthin Biosynthesis in Staphylococcus aureus

  摘要：

  Staphylococcus aureus produces a golden carotenoid virulence factor called staphyloxanthin (STX), and we report here the inhibition of the enzyme, dehydrosqualene synthase (CrtM), responsible for the first committed step in STX biosynthesis. The most active compounds are halogen-substituted phosphonosulfonates, with K-i values as low as 5 nM against the enzyme and IC50 values for STX inhibition in S. aureus as low as 11 nM. There is, however, only a poor correlation (R-2 = 0.27) between enzyme and cell pIC(50) (= -log(10) IC50) values. The ability to predict cell from enzyme data improves considerably (to R-2 = 0.72) with addition of two more descriptors. We also investigated the activity of these compounds against human squalene synthase (SQS), as a counterscreen, finding several potent STX biosynthesis inhibitors with essentially no squalene synthase activity. These results open up the way to developing potent and selective inhibitors of an important virulence factor in S. aureus, a major human pathogen.

  DOI：

  10.1021/jm801023u
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 3-(4-氟苯氧基)苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成 ethyl 3-[3-(4-fluorophenoxy)phenyl]prop-2-enoate
  参考文献：
  名称：

  Phosphonosulfonates Are Potent, Selective Inhibitors of Dehydrosqualene Synthase and Staphyloxanthin Biosynthesis in Staphylococcus aureus

  摘要：

  Staphylococcus aureus produces a golden carotenoid virulence factor called staphyloxanthin (STX), and we report here the inhibition of the enzyme, dehydrosqualene synthase (CrtM), responsible for the first committed step in STX biosynthesis. The most active compounds are halogen-substituted phosphonosulfonates, with K-i values as low as 5 nM against the enzyme and IC50 values for STX inhibition in S. aureus as low as 11 nM. There is, however, only a poor correlation (R-2 = 0.27) between enzyme and cell pIC(50) (= -log(10) IC50) values. The ability to predict cell from enzyme data improves considerably (to R-2 = 0.72) with addition of two more descriptors. We also investigated the activity of these compounds against human squalene synthase (SQS), as a counterscreen, finding several potent STX biosynthesis inhibitors with essentially no squalene synthase activity. These results open up the way to developing potent and selective inhibitors of an important virulence factor in S. aureus, a major human pathogen.

  DOI：

  10.1021/jm801023u

文献信息

• 一种3-芳基丙醇的制备方法
  申请人：江苏扬农化工股份有限公司

  公开号：CN106554259B

  公开（公告）日：2019-05-21

  本发明公开了一种3‑芳基丙醇的制备方法，3‑芳基苯甲醛、乙酸酯在有机溶剂中，一定温度下加入催化剂进行缩合反应制备3‑芳基‑2‑烯酯，3‑芳基‑2‑烯酯和还原剂进行还原反应，最终得到产物3‑芳基丙醇。本发明方法采用芳氧基取代苯甲醛与乙酸酯缩合、再经过还原来制备3‑芳基丙醇，芳醛与乙酸酯在催化剂催化下进行缩合反应制备类似Knoevenagel缩合化合物3‑芳基‑2‑烯酯，再经过还原剂还原制备芳基丙醇，其总收率>80％，含量>95％；本发明使用的原料便宜、来源广，制备方法更加安全、方便，且生产成本低、原料无毒或低毒，总收率高且三废较少，有利于工业化。