4-(4'-硝基苯基)-4-羟基-1-甲基硫烷基-2-丁酮 | 673491-82-2

• 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-甲基硫烷基-2-丁酮
• 英文名称: 4-(4'-nitrophenyl)-4-hydroxy-1-methylsulfanyl-2-butanone
• 英文别名: 4-Hydroxy-1-methylsulfanyl-4-(4-nitrophenyl)butan-2-one
• CAS: 673491-82-2
• 化学式: C₁₁H₁₃NO₄S
• 分子量: 255.295
• InChiKey: CPIUKRRVJINGPX-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  435.3±45.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  108
• 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-甲基硫烷基-2-丁酮 在 PBS buffer 作用下， 以 乙腈 为溶剂， 生成 (4S)-4-hydroxy-1-methylsulfanyl-4-(4-nitrophenyl)butan-2-one
  参考文献：
  名称：

  对映体富集的硫烷基羟醛产品的生物催化途径

  摘要：

  衍生自含硫或硒的受体的醛醇缩合产物是在抗体84G3存在下，通过对映体过量范围为56％至70％的动力学拆分制备的。对于衍生自具有三个不同受体的硫代甲氧基丙酮的硫烷基醛醇缩醛产物，其对映选择性的水平更高（对映体过量均超过96％）。

  DOI：

  10.1016/j.tet.2004.06.033
• 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 4-(4'-硝基苯基)-4-羟基-1-甲基硫烷基-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

• 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。
• 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
• A biocatalytic route to enantioenriched, sulfanyl aldol products
  作者：C. Baker-Glenn、R. Ancliff、V. Gouverneur

  DOI：10.1016/j.tet.2004.06.033

  日期：2004.8

  The aldol products derived from sulfur- or selenium containing acceptors were prepared by kinetic resolution in the presence of antibody 84G3 with enantiomeric excesses ranging from 56 to 70%. Much higher level of enantioselectivity was obtained (enantiomeric excesses all superior to 96%) for sulfanyl aldol products derived from thiomethoxyacetone with three different acceptors.

  衍生自含硫或硒的受体的醛醇缩合产物是在抗体84G3存在下，通过对映体过量范围为56％至70％的动力学拆分制备的。对于衍生自具有三个不同受体的硫代甲氧基丙酮的硫烷基醛醇缩醛产物，其对映选择性的水平更高（对映体过量均超过96％）。
• 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.