3,5-Bis(naphthalen-1-ylmethyl)-4,5-dihydro-1,2-oxazole | 184166-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,5-Bis(naphthalen-1-ylmethyl)-4,5-dihydro-1,2-oxazole
• CAS: 184166-24-3
• 化学式: C₂₅H₂₁NO
• 分子量: 351.448
• InChiKey: RRROVKYPQXHILA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-Bis(naphthalen-1-ylmethyl)-4,5-dihydro-1,2-oxazole 在 镍 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到4-Hydroxy-1,5-dinaphthalen-1-ylpentan-2-one
  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
• 作为产物：
  描述：

  1-烯丙基萘 、 1-naphthylacetaldoxime 在 吡啶 、 sodium hypochlorite 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以84%的产率得到3,5-Bis(naphthalen-1-ylmethyl)-4,5-dihydro-1,2-oxazole
  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

• 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.