(R)-1-(4'-nitrophenyl)-1-hydroxy-3-heptanone

• 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: (R)-1-(4'-nitrophenyl)-1-hydroxy-3-heptanone
• 英文别名: 1-(4-nitrophenyl)-1-hydroxy-3-heptanone；(1R)-1-hydroxy-1-(4-nitrophenyl)heptan-3-one
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: TWZZPJXIQLMNKC-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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 84G₃ aldolase antibody 作用下， 以 水 、 乙腈 为溶剂， 反应 26.0h， 生成 (R)-1-(4'-nitrophenyl)-1-hydroxy-3-heptanone
  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

• Substrate selective catalytic molecular hydrogels: the role of the hydrophobic effect
  作者：Cristina Berdugo、Juan F. Miravet、Beatriu Escuder

  DOI：10.1039/c3cc45623d

  日期：——

  A catalytic hydrogel is reported for the substrate selective direct aldol reaction of aliphatic ketones based on their hydrophobicity and on the emergence of catalytic activity only after self-assembly of the catalyst.

  据报道，基于疏水性选择性底物和催化剂自组装后催化活性出现的直接aldol反应，报道了一种用于脂肪族酮的催化水凝胶。
• Recyclable chiral diamine–polyoxometalate (POM) acids catalyzed asymmetric direct aldol reaction of aromatic aldehydes with long-chain aliphatic ketones
  作者：Qiang Gao、Sheng-Mei Lu、Yan Liu、Can Li

  DOI：10.1016/j.tetlet.2011.05.053

  日期：2011.7

  In this Letter, we studied the asymmetric direct aldol reaction of long-chain aliphatic ketones with aromatic aldehydes, using chiral diamine–polyoxometalate acid combined organocatalysts. High yields (up to 90%) and enantioselectivities (up to 90% ee) were obtained under solvent-free conditions with the optimized catalyst. Furthermore, such organocatalysts could be easily recycled and reused for four

  在这封信中，我们使用手性二胺-多金属氧酸盐酸组合的有机催化剂研究了长链脂肪族酮与芳族醛的不对称直接羟醛反应。在无溶剂条件下，使用优化的催化剂可获得高收率（最高90％）和对映选择性（最高90％ee）。此外，这种有机催化剂可以容易地再循环和再使用四次而不会显着损失反应性和对映选择性。
• Organo-catalyzed highly diastereo- and enantio-selective direct aldol reactions in water
  作者：Jun-Feng Zhao、Long He、Jun Jiang、Zhuo Tang、Lin-Feng Cun、Liu-Zhu Gong

  DOI：10.1016/j.tetlet.2008.03.131

  日期：2008.5

  The asymmetric direct aldol reactions of a wide scope of aromatic aldehydes, with unmodified ketones in the presence of 1 mol % of organocatalyst prepared from (2R,3R)-diethyl 2-amino-3-hydroxysuccinate and trans-4-hydroxy-l-proline, were performed in water, affording aldol products in high yields with excellent diastereoselectivities of up to >99:1 and enantioselectivities of up to 98%.

  在1 mol％由（2 R，3 R）-2-乙基-2-氨基-3-羟基琥珀酸二乙酯和反式-4-羟基-羟基乙酸制备的有机催化剂存在下，各种芳香醛与未改性的酮发生不对称直接羟醛反应l-脯氨酸在水中进行，以高收率提供羟醛产物，其非对映选择性高达> 99：1，对映选择性高达98％。
• 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
• 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.