4-(4'-硝基苯基)-4-羟基-1-甲氧基-2-丁酮 | 673491-75-3

• 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: 4-(4'-硝基苯基)-4-羟基-1-甲氧基-2-丁酮
• 英文名称: 4-(4'-nitrophenyl)-4-hydroxy-1-methoxy-2-butanone
• 英文别名: 4-Hydroxy-1-methoxy-4-(4-nitrophenyl)butan-2-one
• CAS: 673491-75-3
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: PFTKFJVKQQGBMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C
• 沸点：
  421.2±40.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4'-硝基苯基)-4-羟基-1-甲氧基-2-丁酮 在 phosphate-buffered saline 、 aldolase I antibody 84G₃ 作用下， 生成 1-甲氧基-2-丙酮 、 对硝基苯甲醛 、 (4S)-4-hydroxy-1-methoxy-4-(4-nitrophenyl)butan-2-one
  参考文献：
  名称：

  Unprecedented Regiocontrol Using An Aldolase I Antibody

  摘要：

  DOI：

  10.1002/1521-3773(20020315)41:6<1012::aid-anie1012>3.0.co;2-i
• 作为产物：
  描述：

  1-(4'-硝基苯基)-1-羟基-5-甲氧基-3-戊酮 在 84G₃ aldolase antibody 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 4-(4'-硝基苯基)-4-羟基-1-甲氧基-2-丁酮
  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

• Recoverable silica-gel supported binam-prolinamides as organocatalysts for the enantioselective solvent-free intra- and intermolecular aldol reaction
  作者：Abraham Bañón-Caballero、Gabriela Guillena、Carmen Nájera、Enrico Faggi、Rosa María Sebastián、Adelina Vallribera

  DOI：10.1016/j.tet.2012.11.097

  日期：2013.1

  supported binam-derived prolinamides are efficient organocatalysts for the direct intramolecular and intermolecular aldol reaction under solvent-free conditions using conventional magnetic stirring. These organocatalysts in combination with benzoic acid showed similar results to those obtained under similar homogeneous reaction conditions using an organocatalyst of related structure. For the intermolecular process

  硅胶负载的比纳姆衍生的脯氨酰胺是使用常规磁力搅拌在无溶剂条件下直接进行分子内和分子间羟醛直接反应的有效有机催化剂。这些与苯甲酸组合的有机催化剂显示出与使用相关结构的有机催化剂在相似的均相反应条件下获得的结果相似的结果。对于分子间方法，羟醛产物是在室温下且仅使用2当量的酮获得的，具有高产率，区域，非对映和对映选择性。在这些反应条件下，醛之间的交叉羟醛反应也是可能的。回收的催化剂最多可重复使用九次，从而获得相似的结果。更有趣的是，
• Solvent-free direct enantioselective aldol reaction using polystyrene-supported N-sulfonyl-(Ra)-binam-d-prolinamide as a catalyst
  作者：Abraham Bañón-Caballero、Gabriela Guillena、Carmen Nájera

  DOI：10.1039/c002967j

  日期：——

  catalytic system for the enantioselective direct aldol reaction between different ketones and aldehydes under solvent-free or aqueous conditions. The polystyrene-supported N-sulfonyl-(Ra)-binam-D-prolinamide catalyst in combination with benzoic acid showed similar results to those obtained with unsupported N-tosyl-binam-derived prolinamide under similar reaction conditions. The aldol products were obtained

  的固定 N-磺酰基-（R a）-比纳姆-D-脯氨酰胺 使用聚苯乙烯作为载体可以回收有效的 催化在无溶剂或水性条件下，不同酮和醛之间的对映选择性直接羟醛反应的体系。聚苯乙烯负载的N-磺酰基-（R a）-Binam- D-脯氨酰胺催化剂与苯甲酸显示出与不支持的N-甲苯磺酰基-比纳姆衍生的结果相似的结果脯氨酰胺在相似的反应条件下 羟醛产品是在室温下仅使用2当量的酮具有高收率，区域，非对映和对映选择性。醛之间的醛醇缩合反应也可以在这些反应条件下进行，结果适中。恢复催化剂 最多可以重复使用六次，而不会影响所获得的结果。
• <i>N</i>-Tosyl-(<i>S</i>_a)-binam-<scp>l</scp>-prolinamide as Highly Efficient Bifunctional Organocatalyst for the General Enantioselective Solvent-Free Aldol Reaction
  作者：Gabriela Guillena、Carmen Nájera、Santiago Viózquez

  DOI：10.1055/s-0028-1087349

  日期：2008.12

  N-Tosyl-(S a)-binam-l-prolinamide (5 mol%) and benzoic acid (1 mol%) were used as catalysts in the enantioselective direct aldol reaction between different ketones and aldehydes under solvent-free conditions in the presence or absence of water. Under these reaction conditions it was possible to reduce the amount of required ketone to two equivalents to give the corresponding aldol products with high yields, regio-, diastereo- and enantioselectivities. The aldol reaction between aldehydes or the intramolecular aldol reaction can be also performed with excellent results.

  在有水或无水的无溶剂条件下，N-对甲苯磺酰基-(S a)-binam-l-脯氨酰胺（5 摩尔%）和苯甲酸（1 摩尔%）被用作催化剂，用于不同酮和醛之间的对映体选择性直接醛醇反应。在这些反应条件下，可以将所需酮的量减少到两个当量，从而得到相应的醛醇产物，并具有高产率、区域、非对映和对映选择性。醛与醛之间的醛醇反应或分子内醛醇反应也可以进行，而且效果极佳。
• 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.
• Unprecedented Regiocontrol Using An Aldolase I Antibody
  作者：Virginie Maggiotti、Marina Resmini、Véronique Gouverneur

  DOI：10.1002/1521-3773(20020315)41:6<1012::aid-anie1012>3.0.co;2-i

  日期：2002.3.15