1,2-bis-(2,4-difluorophenyl)-2-hydroxyethan-1-one | 942406-96-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis-(2,4-difluorophenyl)-2-hydroxyethan-1-one
• 英文别名: 1,2-Bis(2,4-difluorophenyl)-2-hydroxyethanone
• CAS: 942406-96-4
• 化学式: C₁₄H₈F₄O₂
• 分子量: 284.21
• InChiKey: MOZRQJUPHVESBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis-(2,4-difluorophenyl)-2-hydroxyethan-1-one 在 硝酸铵 、 copper diacetate 、 溶剂黄146 作用下， 反应 90.0h， 以95%的产率得到2,2',4,4'-tetrafluorobenzil
  参考文献：
  名称：

  Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils

  摘要：

  We have synthesized and assessed the ability of symmetrical fluorobenzoins and fluorobenzils to inhibit mammalian carboxylesterases (CE). The majority of the latter were excellent inhibitors of CEs however unexpectedly, the fluorobenzoins were very good enzyme inhibitors. Positive correlations were seen with the charge on the hydroxyl carbon atom, the carbonyl oxygen, and the Hammett constants for the derived K-i values with the fluorobenzoins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.012
• 作为产物：
  描述：

  2,4-二氟苯甲醛 在 sodium hydroxide 、 盐酸硫胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以67%的产率得到1,2-bis-(2,4-difluorophenyl)-2-hydroxyethan-1-one
  参考文献：
  名称：

  Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils

  摘要：

  We have synthesized and assessed the ability of symmetrical fluorobenzoins and fluorobenzils to inhibit mammalian carboxylesterases (CE). The majority of the latter were excellent inhibitors of CEs however unexpectedly, the fluorobenzoins were very good enzyme inhibitors. Positive correlations were seen with the charge on the hydroxyl carbon atom, the carbonyl oxygen, and the Hammett constants for the derived K-i values with the fluorobenzoins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.012

文献信息

• Benzaldehyde Lyase-Catalyzed Enantioselective Carboligation of Aromatic Aldehydes with Mono- and Dimethoxy Acetaldehyde
  作者：Ayhan S. Demir、Özge Şeşenoglu、Pascal Dünkelmann、Michael Müller

  DOI：10.1021/ol034415b

  日期：2003.6.1

  Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
• Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils
  作者：Latorya D. Hicks、Janice L. Hyatt、Teri Moak、Carol C. Edwards、Lyudmila Tsurkan、Monika Wierdl、Antonio M. Ferreira、Randy M. Wadkins、Philip M. Potter

  DOI：10.1016/j.bmc.2007.03.012

  日期：2007.6.1

  We have synthesized and assessed the ability of symmetrical fluorobenzoins and fluorobenzils to inhibit mammalian carboxylesterases (CE). The majority of the latter were excellent inhibitors of CEs however unexpectedly, the fluorobenzoins were very good enzyme inhibitors. Positive correlations were seen with the charge on the hydroxyl carbon atom, the carbonyl oxygen, and the Hammett constants for the derived K-i values with the fluorobenzoins. (c) 2007 Elsevier Ltd. All rights reserved.