1-(4'-硝基苯基)-1-羟基-3-己酮 | 673491-67-3

• 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-(4'-硝基苯基)-1-羟基-3-己酮
• 英文名称: 1-hydroxy-1-(4-nitrophenyl)hexan-3-one
• CAS: 673491-67-3
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: QEGXDVYUEUIOCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4'-硝基苯基)-1-羟基-3-己酮 在 84G₃ aldolase antibody 作用下， 以 水 、 乙腈 为溶剂， 生成 对硝基苯甲醛 、 2-戊酮 、 (S)-1-(4'-nitrophenyl)-1-hydroxy-3-hexanone
  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)-1-羟基-5-甲氧基-3-戊酮 在 sodium hydroxide 、 84G₃ aldolase antibody 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(4'-硝基苯基)-1-羟基-3-己酮
  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

• Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction
  作者：Xing-Wen Feng、Chao Li、Na Wang、Kun Li、Wei-Wei Zhang、Zao Wang、Xiao-Qi Yu

  DOI：10.1039/b914653a

  日期：——

  Acrylic resin immobilized Candida antarctica lipase B (CAL-B) is able to catalyse decarboxylative aldol reaction and decarboxylative Knoevenagel reaction with good to excellent yields.

  聚丙烯酸树脂固定化的南极酵母脂肪酶B (CAL-B) 能够催化脱羧醇缩反应和脱羧Knoevenagel反应，且产率良好到优秀。
• One-pot bienzymatic cascade combining decarboxylative aldol reaction and kinetic resolution to synthesize chiral β-hydroxy ketone derivatives
  作者：Fan Xu、Jian Xu、Yujing Hu、Xianfu Lin、Qi Wu

  DOI：10.1039/c6ra12729k

  日期：——

  bienzymatic one-pot sequential cascade for the synthesis of (S)-β-hydroxy ketones and acylated (R)-β-hydroxy ketone derivatives was successfully developed. An immobilized lipase from Mucor miehei (MML) catalysed promiscuous decarboxylative aldol reaction and a lipase A or B from Candida antarctica (CAL-A or CAL-B) catalysed kinetic resolution of racemic β-hydroxy ketone were combined in this one-pot protocol

  成功开发了用于合成（S）-β-羟基酮和酰化（R）-β-羟基酮衍生物的双酶一锅顺序级联反应。在此一锅方案中，将来自Mucor miehei（MML）的固定化脂肪酶催化的混杂的脱羧醛醇反应和来自南极假丝酵母的脂肪酶A或B （CAL-A或CAL-B）催化的消旋β-羟基酮的动力学拆分，减少两个反应之间的纯化步骤。通过该方法获得了十二个手性β-羟基酮和相同数量的相应酰化衍生物，它们具有优异的ee值和高收率，并且放大实验在没有明显降低反应速率和立体选择性的情况下也可以进行。
• Antibody-catalyzed decarboxylation and aldol reactions using a primary amine molecule as a functionalized small nonprotein component
  作者：Fumihiro Ishikawa、Kouki Uno、Masao Nishikawa、Takeshi Tsumuraya、Ikuo Fujii

  DOI：10.1016/j.bmc.2013.09.015

  日期：2013.11

  Catalytic antibody 27C1 bears binding sites for both a substrate-and a functionalized small nonprotein component in the active site. We investigated the possibility of exploiting imine and enamine intermediates using a primary amine molecule into the active site of antibody 27C1. The antibody catalyzed beta-keto acid decarboxylation with a rate enhancement (k(cat)/K-m/k(uncat)) of 140,000, as well as highly regioselective cross-aldol reactions of ketones and p-nitrobenzaldehyde. These studies provide new strategies for the generation of catalytic antibodies possessing binding sites for functionalized components. (C) 2013 Elsevier Ltd. All rights reserved.
• Mahajan, Dinesh; Chimni, Swapandeep Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 8, p. 1355 - 1358
  作者：Mahajan, Dinesh、Chimni, Swapandeep Singh

  DOI：——

  日期：——
• 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