1-phenyl-5-(pentafluorophenyl)-4-methoxy-2-pentanone

• 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: 1-phenyl-5-(pentafluorophenyl)-4-methoxy-2-pentanone
• 英文别名: 4-Methoxy-5-(2,3,4,5,6-pentafluorophenyl)-1-phenylpentan-2-one
• 化学式: C₁₈H₁₅F₅O₂
• 分子量: 358.308
• InChiKey: BLFKJAAXEURRDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯乙醛肟 在 镍 吡啶 、 盐酸 、 sodium hypochlorite 、 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 1-phenyl-5-(pentafluorophenyl)-4-methoxy-2-pentanone
  参考文献：
  名称：

  3-Unsubstituted 1,5-Diaryl-2,4-pentanediones and -4-methoxy-2-pentanones:  Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines

  摘要：

  Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1-(arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1,5-diaryl-2,4-pentanediones, or converted to 1,5-diaryl-4-methoxy-2-pentanones by refluxing in methanol in the presence of hydrochloric acid. A detailed study of this general route is reported here.

  DOI：

  10.1021/jo960887a

文献信息

• A general route to 3-unsubstituted 1,5-diaryl-2,4-pentanediones and -4-Methoxy-2-pentanones
  作者：Juha Pulkkinen、Jouko Vepsäläinen、Reino Laatikainen

  DOI：10.1016/0040-4039(94)88376-9

  日期：1994.12

  2-Isoxazolines are converted to corresponding 3-hydroxyketones which are used as precursors to produce new 3-unsubstituted 1,5-diaryl-2,4-pentanediones and -4-methoxy-2-pentanones.

  将2-异恶唑啉转化为相应的3-羟基酮，将其用作前体以生产新的3-未取代的1,5-二芳基-2,4-戊二酮和-4-甲氧基-2-戊酮。
• 3-Unsubstituted 1,5-Diaryl-2,4-pentanediones and -4-methoxy-2-pentanones:  Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines
  作者：Juha T. Pulkkinen、Jouko J. Vepsäläinen

  DOI：10.1021/jo960887a

  日期：1996.1.1

  Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1-(arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1,5-diaryl-2,4-pentanediones, or converted to 1,5-diaryl-4-methoxy-2-pentanones by refluxing in methanol in the presence of hydrochloric acid. A detailed study of this general route is reported here.