(3S,4S)-3-hydroxy-5-nitro-4-phenylpentan-2-one

• 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: (3S,4S)-3-hydroxy-5-nitro-4-phenylpentan-2-one
• 英文别名: (4S)-3-hydroxy-5-nitro-4-phenylpentan-2-one；3-hydroxy-5-nitro-4-phenylpentan-2-one
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: DIHKQFJYRWFMEA-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  反式硝基苯乙烯 、 羟基丙酮 在 (2R,2'R)-1-(1-methylethyl)-2,2'-bipyrrolidine 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 (3S,4S)-3-hydroxy-5-nitro-4-phenylpentan-2-one 、 3-hydroxy-5-nitro-4-phenyl-pentan-2-one
  参考文献：
  名称：

  Organocatalyzed Asymmetric Reactions via Microwave Activation

  摘要：

  Organocatalyzed asymmetric microwave-assisted reactions are described. Significant rate enhancements and a decrease of catalyst loading via microwave activation have been observed, while maintaining good to high yields and selectivities compared to literature results.

  DOI：

  10.1021/ol0614727

文献信息

• A Recyclable Organocatalyst for Asymmetric Michael Addition of Acetone to Nitroolefins
  作者：Aidang Lu、Tao Liu、Ronghua Wu、Youming Wang、Guiping Wu、Zhenghong Zhou、Jianxin Fang、Chuchi Tang

  DOI：10.1021/jo2002819

  日期：2011.5.20

  Based on different chiral diamine skeletons, a series of bifunctional primary amine-thiophosphoramides were synthesized and screened as the catalysts for the asymmetric Michael addition of acetone to both aromatic and aliphatic nitroolefins. Under the catalysis of a thiophosphoramide derived from 1,2-diphenylethane-1,2-diamine, the corresponding adducts were obtained in high yields (up to >99%) with

  基于不同的手性二胺骨架，合成了一系列双官能的伯胺-硫代磷酰胺，并筛选了丙酮不对称地将迈克尔加成至芳族和脂族硝基烯烃的催化剂。在衍生自1,2-二苯基乙烷-1，2-二胺的硫代磷酰胺的催化下，在温和的反应条件下，可以以高收率（高达> 99％）和优异的对映选择性（97-99％ee）获得相应的加合物。此外，可以通过简单的相分离来回收催化剂，并至少重复使用五次，而不会损失催化活性和立体控制。
• Enantioselective conjugate addition of ketones to nitroalkenes catalyzed by pyrrolidine-sulfamides
  作者：Jinjia Wang、Jinhua Lao、Quansheng Du、Shaozhen Nie、Zhipeng Hu、Ming Yan

  DOI：10.1002/chir.21987

  日期：2012.3

  A series of chiral pyrrolidine‐sulfamides were prepared and examined as the catalysts for conjugate addition of ketones to nitroalkenes. Benzoic acid was identified as the most efficient additives for the transformation. Excellent enantioselectivities, diastereoselectivities, and yields were achieved for the reaction of cyclohexanone with β‐aryl nitroethylenes under solvent free conditions. β‐Isopropyl

  制备了一系列手性吡咯烷-磺酰胺，并作为催化剂将酮共轭加成到硝基烯烃中。苯甲酸被认为是转化最有效的添加剂。在无溶剂条件下，环己酮与β-芳基硝基乙烯的反应具有出色的对映选择性，非对映选择性和产率。也可以使用β-异丙基硝基乙烯，经过延长的反应时间后，可以得到具有优异对映选择性的产物。比较具有不同侧链的吡咯烷-磺酰胺类有机催化剂的催化行为表明，对映选择性主要受手性吡咯烷单元控制，侧链上的其他手性中心发挥的作用可忽略不计。提出了硫酰胺和硝基之间的氢键相互作用对于硝基链烯的活化和组织良好的过渡态至关重要。手性，2012年。©2012 Wiley Periodicals，Inc.。
• (S)-Binam-L-prolinamide as organocatalyst for the enantioselective conjugate addition of α-alkoxyketones to β-nitrostyrene derivatives
  作者：Miguel Yus、Gabriela Guillena、Carmen Nájera、Santiago F. Viózquez

  DOI：10.3998/ark.5550190.0012.313

  日期：——

  This research was supported by the Ministerio de Ciencia e Innovacion (Projects CTQ2007-62771/BQU, CTQ2007-65218/BQU and Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (Project PROMETEO/2009/039, FEDER) and the University of Alicante (UA).

  这项研究得到了部长级 Ciencia e Innovacion（项目 CTQ2007-62771/BQU、CTQ2007-65218/BQU 和 Consolider Ingenio 2010 CSD2007-00006）、Generalitat Valenciana（项目 PROMETEO/2009/BQU）和大学的支持阿利坎特 (UA)。
• Organocatalyzed Asymmetric Reactions via Microwave Activation
  作者：Sarah Mossé、Alexandre Alexakis

  DOI：10.1021/ol0614727

  日期：2006.8.1

  Organocatalyzed asymmetric microwave-assisted reactions are described. Significant rate enhancements and a decrease of catalyst loading via microwave activation have been observed, while maintaining good to high yields and selectivities compared to literature results.