1-(2,4-dichlorophenyl)-2,3-epoxy-2-phenylpropan-1-one | 111299-49-1

• 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-(2,4-dichlorophenyl)-2,3-epoxy-2-phenylpropan-1-one
• 英文别名: (2,4-dichlorophenyl)-(2-phenyloxiran-2-yl)methanone
• CAS: 111299-49-1
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: CSHKVGKJGGSEGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-2,3-epoxy-2-phenylpropan-1-one 在 (diethylamido)sulfur trifluoride 作用下， 以 四氯化碳 、 二氯甲烷 、 异丙醇 为溶剂， 反应 0.75h， 生成 1-(2,4-dichlorophenyl)-2-fluoro-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one
  参考文献：
  名称：

  2-Chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one hydrochloride, a novel, nonmutagenic antibacterial with specific activity against anaerobic bacteria

  摘要：

  1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.

  DOI：

  10.1021/jm00112a006
• 作为产物：
  描述：

  1-(2,4-二氯苯基)-2-苯基丙-2-烯-1-酮 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以66%的产率得到1-(2,4-dichlorophenyl)-2,3-epoxy-2-phenylpropan-1-one
  参考文献：
  名称：

  2-Chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one hydrochloride, a novel, nonmutagenic antibacterial with specific activity against anaerobic bacteria

  摘要：

  1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.

  DOI：

  10.1021/jm00112a006

文献信息

• One-pot synthesis of α,β-epoxy ketones by palladium-catalyzed epoxidation–oxidation of terminal allylic alcohols
  作者：Fateh V. Singh、Jesus M. Pena、Hélio A. Stefani

  DOI：10.1016/j.tetlet.2010.01.065

  日期：2010.3

  herein is a one-pot synthesis of α,β-epoxy ketones using a palladium-catalyzed epoxidation–oxidation sequence. Functionalized terminal allylic alcohols are treated with m-CPBA under mild reaction conditions to obtain the α,β-epoxy ketones. The main benefit of this approach is that the epoxidation of the terminal double bond and the oxidation of the secondary alcohol occured in the same reaction under

  本文描述的是使用钯催化的环氧化-氧化顺序一锅法合成的α，β-环氧酮。官能终端烯丙基醇与处理米温和反应条件下-CPBA以获得α，β环氧酮。该方法的主要优点是，在温和的反应下，同一反应中发生了末端双键的环氧化和仲醇的氧化，并且在反应顺序中既允许了给电子功能，又吸收了吸电子功能。