(R)-3-hydroxy-3-(3-nitrophenyl)-1-phenylpropan-1-one | 1027476-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-3-hydroxy-3-(3-nitrophenyl)-1-phenylpropan-1-one
• 英文别名: (r)-3-Hydroxy-3-(3-nitrophenyl)-1-phenyl-propan-1-one；(3R)-3-hydroxy-3-(3-nitrophenyl)-1-phenylpropan-1-one
• CAS: 1027476-53-4
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: XJEKGXBREWDKEG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  间硝基苯甲醛 、 苯乙酮 在 (S)-2-(trifluoromethane-sulfonylamino-methyl)-pyrrolidine 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 (R)-3-hydroxy-3-(3-nitrophenyl)-1-phenylpropan-1-one 、 (S)-3-hydroxy-3-(3-nitrophenyl)-1-phenylpropan-1-one
  参考文献：
  名称：

  （S）-吡咯烷磺酰胺催化的芳基甲基酮与芳基醛的不对称直接羟醛反应

  摘要：

  已经开发了具有中等至良好对映选择性的（S）-吡咯烷磺酰胺催化的芳基甲基酮与芳族醛的不对称直接羟醛反应。该研究大大拓宽了手性胺促进的羟醛工艺的底物范围。

  DOI：

  10.1016/j.tetlet.2008.02.164

文献信息

• Direct Asymmetric Aldol Reaction of Aryl Ketones with Aryl Aldehydes Catalyzed by Chiral BINOL-Derived Zincate Catalyst
  作者：Hong Li、Chao-Shan Da、Yu-Hua Xiao、Xiao Li、Ya-Ning Su

  DOI：10.1021/jo801182n

  日期：2008.9.19

  Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral metal complex is reported for the first time herein. Two novel semicrown chiral ligands 1a and 1b were synthesized from (S)- and (R)-BINOL, respectively, and then employed to catalyze the direct asymmetric aldol addition of aryl ketones to aryl aldehydes. Introduced with 2.0 equiv of diethylzinc, 1b had higher

  本文首次报道了手性金属络合物催化的芳基酮与芳基醛的直接不对称醛醇缩合反应。分别从（S）-和（R）-BINOL合成了两个新颖的半冠手性配体1a和1b，然后用于催化芳基酮与芳基醛的直接不对称羟醛加成。引入2.0当量的二乙基锌后，1b的对映选择性高于1a。获得了高达97％的产率和高达80％的对映选择性。
• Direct asymmetric aldol reaction of acetophenones with aromatic aldehydes catalyzed by chiral Al/Zn heterobimetallic compounds
  作者：Xiao Li、Lei Zhang、Yu-Hua Xiao、Qi-Peng Guo、Chao-Shan Da、Hong Li、Xiaoju Liu、Xiangrong Ma、Yajun Ma

  DOI：10.1134/s1070363216080247

  日期：2016.8

  Chiral Al/Zn heterobimetallic complexes are effective catalysts for the direct highly enantioselective aldol reaction of acetophenones with aromatic aldehydes. The Al site in the complex acts as a Lewis acid to activate aldehyde, whereas ethylzinc alkoxide plays a role of a Brønsted base to form a reactive zinc enolate with acetophenone. Distinct nature of two different metals contributes to the efficient

  手性Al / Zn异双金属配合物是苯乙酮与芳族醛直接高对映选择性醛醇缩合反应的有效催化剂。络合物中的Al位点起路易斯酸的作用来活化醛，而乙基锌醇盐起布朗斯台德碱的作用，与苯乙酮形成反应性烯醇锌。两种不同金属的不同性质有助于有效的直接不对称醛醇缩合反应。
• <i>N</i>-Triflylthiophosphoramide Catalyzed Enantioselective Mukaiyama Aldol Reaction of Aldehydes with Silyl Enol Ethers of Ketones
  作者：Cheol Hong Cheon、Hisashi Yamamoto

  DOI：10.1021/ol100233t

  日期：2010.6.4

  The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid

  已经报道了使用酮的甲硅烷基烯醇醚作为亲核试剂的第一个布朗斯台德酸催化醛的不对称 Mukaiyama 羟醛反应。各种醛和酮的甲硅烷基烯醇醚以优异的产率和良好的对映选择性提供了醛醇产物。机理研究表明，实际的催化剂可能会根据反应温度从甲硅烷基化布朗斯台德酸变为布朗斯台德酸本身。
• Investigations of enantioreversal in both direct and directed enantioselective aldol reactions catalyzed by CuCl2[(−)-sparteine] and NiCl2[(−)-sparteine] complexes
  作者：H. Maheswaran、P.J. Amal Joseph、K. Leon Prasanth、S. Priyadarshini、P. Satyanarayana、Praveen R. Likhar、M. Lakshmi Kantam

  DOI：10.1016/j.tetasy.2010.07.008

  日期：2010.9

  chiral [CuCl2(sparteine)] 1 and [NiCl2(sparteine)] 2 complexes as catalysts under fluoride anion-promoted double catalytic activation (DCA) conditions cause enantioreversal in the asymmetric Mukaiyama aldol reaction of 1-phenyl-1-trimethylsiloxyethylene with various aromatic aldehydes. A similar enantioreversal also occurs in the direct aldol reaction between methyl vinyl ketone and various aromatic aldehydes

  在氟化物阴离子促进的双催化活化（DCA）条件下，使用结构明确的手性[CuCl 2（sparteine）] 1和[NiCl 2（sparteine）] 2配合物作为催化剂，导致1的不对称Mukaiyama aldol反应中发生对映逆转。 -苯基-1-三甲基甲硅烷氧基乙烯与各种芳香醛。在Et 3 N促进的DCA条件下，甲基乙烯基酮与各种芳族醛之间的直接羟醛反应中也发生类似的对映逆转。我们已经使用组理论分析通过对称变形坐标对分子1和2的分子结构进行了定量分析根据X射线结构数据；研究结果表明，其分子结构中存在的先天立体化学差异构成了不对称CC键形成醛醇缩合反应中对映反转现象的基础。
• Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine
  作者：Lei Li、Shaohua Gou、Fei Liu

  DOI：10.1016/j.tetasy.2013.11.017

  日期：2014.1

  The enantioselective organocatalytic direct aldol reactions of ketones with various aldehydes were developed by using chiral 1,2-cyclohexanediamine COACH) based multifunctional ligands via a noncovalent catalysis mechanism. By using a catalyst, we also obtained functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields and with good to excellent enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.