1-diazo-4-(3,4-dichlorophenyl)-4-phenylbutan-2-one | 1198097-89-0

• 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-diazo-4-(3,4-dichlorophenyl)-4-phenylbutan-2-one
• CAS: 1198097-89-0
• 化学式: C₁₆H₁₂Cl₂N₂O
• 分子量: 319.19
• InChiKey: OHYWMDQRRBQEEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-diazo-4-(3,4-dichlorophenyl)-4-phenylbutan-2-one 在 silver benzoate 作用下， 以 三乙胺 为溶剂， 反应 0.25h， 以77%的产率得到4-(3,4-二氯苯基)-4-苯基丁酸甲酯
  参考文献：
  名称：

  肉桂酸甲酯与亚砷二唑鎓盐的Heck反应的非对映选择性的显着电子效应：（±）-茚达林和（±）-Sertraline的正式全合成

  摘要：

  Abstractmagnified imageAn efficient and stereoselective protocol for the preparation of β,β‐disubstituted acrylates in good to high yields by means of a Heck–Matsuda arylation was accomplished. The method employs a base‐ and ligand‐free Heck arylation reaction of methyl cinnamate using both electron‐deficient and electron‐rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3‐arylindanones and 4‐aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (±)‐indatraline and (±)‐sertraline.

  DOI：

  10.1002/adsc.200900032
• 作为产物：
  描述：

  重氮甲烷 、 3-(3,4-二氯苯基)-3-苯丙酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以95%的产率得到1-diazo-4-(3,4-dichlorophenyl)-4-phenylbutan-2-one
  参考文献：
  名称：

  肉桂酸甲酯与亚砷二唑鎓盐的Heck反应的非对映选择性的显着电子效应：（±）-茚达林和（±）-Sertraline的正式全合成

  摘要：

  Abstractmagnified imageAn efficient and stereoselective protocol for the preparation of β,β‐disubstituted acrylates in good to high yields by means of a Heck–Matsuda arylation was accomplished. The method employs a base‐ and ligand‐free Heck arylation reaction of methyl cinnamate using both electron‐deficient and electron‐rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3‐arylindanones and 4‐aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (±)‐indatraline and (±)‐sertraline.

  DOI：

  10.1002/adsc.200900032