1-氯-4-羟基-4-(4-硝基苯基)丁烷-2-酮 | 673492-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-氯-4-羟基-4-(4-硝基苯基)丁烷-2-酮
• 英文名称: 1-chloro-4-hydroxy-4-(4'-nitrophenyl)-butan-2-one
• 英文别名: 1-Chloro-4-hydroxy-4-(4-nitrophenyl)butan-2-one；1-chloro-4-hydroxy-4-(4-nitrophenyl)butan-2-one
• CAS: 673492-14-3
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: UOCIMMXMTJMEOU-UHFFFAOYSA-N

物化性质

• 沸点：
  423.2±40.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  4

反应信息

• 作为产物：
  描述：

  1-(4'-硝基苯基)-1-羟基-5-甲氧基-3-戊酮 在 phosphate buffered saline 、 84G₃ aldolase antibody 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-氯-4-羟基-4-(4-硝基苯基)丁烷-2-酮
  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

• Highly stereoselective direct aldol reactions catalyzed by (S)-NOBIN-l-prolinamide
  作者：Alessio Russo、Giovanna Botta、Alessandra Lattanzi

  DOI：10.1016/j.tet.2007.09.027

  日期：2007.11

  (S)-NOBIN-L-prolinamide was employed as organocatalyst in the direct aldol reactions of different ketones and aromatic aldehydes using dioxane as solvent and in the presence of water as additive. Acetone led to the aldol products in up to 93% ee, while cyclic ketones furnished the anti-aldols in moderate to high yield, excellent diastereoselectivity (up to > 99/< 1 anti/syn ratio) and high ee (up to 95%). (c) 2007 Elsevier Ltd. All rights reserved.
• Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones
  作者：V Maggiotti、S Bahmanyar、M Reiter、M Resmini、K.N Houk、V Gouverneur

  DOI：10.1016/j.tet.2003.10.115

  日期：2004.1

  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.