1-fluoro-4-hydroxy-4-(4'-nitrophenyl)-butan-2-one | 673492-15-4

• 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-fluoro-4-hydroxy-4-(4'-nitrophenyl)-butan-2-one
• 英文别名: 1-Fluoro-4-hydroxy-4-(4-nitrophenyl)butan-2-one
• CAS: 673492-15-4
• 化学式: C₁₀H₁₀FNO₄
• 分子量: 227.192
• InChiKey: KDMRVWDJWFYDSE-UHFFFAOYSA-N

物化性质

• 沸点：
  406.2±40.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-fluoro-4-hydroxy-4-(4'-nitrophenyl)-butan-2-one 在 84G₃ aldolase antibody 作用下， 以 水 、 乙腈 为溶剂， 生成 氟代丙酮 、 对硝基苯甲醛 、 1-fluoro-4-hydroxy-4-(4-nitrophenyl)butan-2-one 、 (S)-1-fluoro-4-hydroxy-4-(4'-nitrophenyl)-butan-2-one
  参考文献：
  名称：

  Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones

  摘要：

  A catalytic regio- and enantioselective aldol reaction of various unsymmetrical methyl ketones with para-nitrobenzaldehyde has been developed using aldolase antibodies as the catalysts. It has been found that the sense and level of regioselectivity for the reactions catalysed by antibody 38C2 and 33F12 are highly dependent on the structure of both the donor and the acceptor but in contrast, antibodies 84G3 and 93F3 catalyse the exclusive formation of the linear regioisomer independent of the structure of the reactants examined. The level of enantiocontrol is very high for most reactions. Both linear aldol enantiomers could be accessed through aldol or retro-aldol reactions using the same antibody. Theoretical studies on regioisomeric alpha- and beta-heteroatom substituted enamines derived from unsymmetrical ketones suggest that most of the linear aldol products formed in the presence of antibodies 84G3 and 93F3 must be formed from intermediate enamines which are not the thermodynamically most favourable. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.115
• 作为产物：
  描述：

  1-(4-硝基苯基)-3-氧代-1-丁醇 在 咪唑 、 三氟甲磺酸三甲基硅酯 、 lutidine 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 1-fluoro-4-hydroxy-4-(4'-nitrophenyl)-butan-2-one
  参考文献：
  名称：

  Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones

  摘要：

  A catalytic regio- and enantioselective aldol reaction of various unsymmetrical methyl ketones with para-nitrobenzaldehyde has been developed using aldolase antibodies as the catalysts. It has been found that the sense and level of regioselectivity for the reactions catalysed by antibody 38C2 and 33F12 are highly dependent on the structure of both the donor and the acceptor but in contrast, antibodies 84G3 and 93F3 catalyse the exclusive formation of the linear regioisomer independent of the structure of the reactants examined. The level of enantiocontrol is very high for most reactions. Both linear aldol enantiomers could be accessed through aldol or retro-aldol reactions using the same antibody. Theoretical studies on regioisomeric alpha- and beta-heteroatom substituted enamines derived from unsymmetrical ketones suggest that most of the linear aldol products formed in the presence of antibodies 84G3 and 93F3 must be formed from intermediate enamines which are not the thermodynamically most favourable. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.115

文献信息

• Amino alcohol catalyzed direct asymmetric aldol reactions: enantioselective synthesis of anti -α-fluoro-β-hydroxy ketones
  作者：Guofu Zhong、Junhua Fan、Carlos F. Barbas

  DOI：10.1016/j.tetlet.2004.05.107

  日期：2004.7

  Prolinol but not proline-(a recently established catalyst of simple intermolecular aldol reactions) was found to be an efficient catalyst for fluoroaldol reactions providing anti-alpha-fluoro-beta-hydroxy ketones with good regio-, diasterio-, and enantio-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.