(4R)-4-(2-氯-5-硝基苯基)-4-羟基丁烷-2-酮 | 815575-78-1

• 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: (4R)-4-(2-氯-5-硝基苯基)-4-羟基丁烷-2-酮
• 英文名称: (4R)-hydroxy-4-(2'-chloro-5'-nitrophenyl)-butan-2-one
• 英文别名: (4R)-hydroxy-4-(2'-chloro-5'-nitrophenyl)butan-2-one；2-Butanone, 4-(2-chloro-5-nitrophenyl)-4-hydroxy-, (4R)-；(4R)-4-(2-chloro-5-nitrophenyl)-4-hydroxybutan-2-one
• CAS: 815575-78-1
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: OXMBFBXGHFWJMN-SNVBAGLBSA-N

物化性质

• 沸点：
  384.1±42.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  二丙酮醇 、 2-氯-5-硝基苯甲醛 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 4.08h， 生成 (4R)-4-(2-氯-5-硝基苯基)-4-羟基丁烷-2-酮 、 (4S)-hydroxy-4-(2'-chloro-5'-nitrophenyl)-butan-2-one
  参考文献：
  名称：

  l-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions

  摘要：

  L-Proline-catalysed direct asymmetric aldol reaction of acetone with various aldehydes in PEG-400 is described. Recycling of the catalyst and solvent (PEG) was possible up to ten runs without loss of catalyst activity. L-Proline was also found to be an efficient catalyst for the asymmetric transfer aldol reaction between various aldehydes and diacetone alcohol for the first time. Good yields and enantioselectivities were observed with both methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.122

文献信息

• Chiral Ionic Liquid Containing L-Proline Unit as a Highly Efficient and Recyclable Asymmetric Organocatalyst for Aldol Reaction
  作者：Li Zhou、Lei Wang

  DOI：10.1246/cl.2007.628

  日期：2007.5.5

  A functionalized chiral ionic liquid (CIL) containing L-proline unit exhibits as a highly efficient and recyclable asymmetric organocatalyst for aldol condensation of aldehydes and ketones in [Bmim...

  含有 L-脯氨酸单元的功能化手性离子液体 (CIL) 是一种高效且可回收的不对称有机催化剂，用于 [Bmim...
• Merrifield Resin Supported Ionic Liquids/l-Proline as Efficient and Recyclable Catalyst Systems for Asymmetric Aldol Reaction
  作者：Xiuli Zhang、Lei Wang、Zuli Wang、Jincan Yan

  DOI：10.1055/s-0029-1217013

  日期：2009.11

  Merrifield resin supported ionic liquids/l-proline as efficient and recyclable catalyst systems for asymmetric aldol reaction have been developed. l-Proline with Merrifield resin supported ionic liquids can catalyze asymmetric aldol reaction smoothly and generate the corresponding products in good to excellent yields and ee values. In addition, the supported catalyst systems can be recycled simply by filtration

  已经开发出Merrifield树脂负载的离子液体/ 1-脯氨酸作为用于不对称醛醇缩合反应的有效且可回收的催化剂体系。l-脯氨酸与Merrifield树脂负载的离子液体可以平稳地催化不对称的羟醛反应，并以高至极好的收率和ee值生成相应的产物。另外，负载的催化剂体系可以通过过滤简单地再循环并重复使用五次而不会显着降低活性。 的Merrifield树脂-有机催化剂-醛醇缩合反应-升-脯氨酸-离子液体-载体上的催化剂
• Asymmetric aldol reactions in poly(ethylene glycol) catalyzed by l-proline
  作者：S. Chandrasekhar、Ch. Narsihmulu、N.Ramakrishna Reddy、S.Shameem Sultana

  DOI：10.1016/j.tetlet.2004.03.116

  日期：2004.5

  A rapid L-proline catalyzed direct aldol reaction between various aldehydes and acetone was achieved using PEG as the solvent with comparable enantioselectivities and yields to those obtained in other solvents. Recycling the catalyst and solvent (PEG) was possible 10 times without loss of activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Proline–threonine dipeptide as an organocatalyst for the direct asymmetric aldol reaction
  作者：Srivari Chandrasekhar、Kancharla Johny、Chada Raji Reddy

  DOI：10.1016/j.tetasy.2009.06.018

  日期：2009.8

  A new proline-threonine (H-Pro-Thr-OH) dipeptide has been demonstrated as an efficient organocatalyst for a direct asymmetric aldol reaction. It was found that this new peptide-based catalyst efficiently catalyzed the reaction between an aldehyde and acetone to provide beta-hydroxy ketones in good yields with good enantioselectivities. (c) 2009 Elsevier Ltd. All rights reserved.
• l-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions
  作者：S. Chandrasekhar、N. Ramakrishna Reddy、S. Shameem Sultana、Ch. Narsihmulu、K. Venkatram Reddy

  DOI：10.1016/j.tet.2005.09.122

  日期：2006.1

  L-Proline-catalysed direct asymmetric aldol reaction of acetone with various aldehydes in PEG-400 is described. Recycling of the catalyst and solvent (PEG) was possible up to ten runs without loss of catalyst activity. L-Proline was also found to be an efficient catalyst for the asymmetric transfer aldol reaction between various aldehydes and diacetone alcohol for the first time. Good yields and enantioselectivities were observed with both methods. (c) 2005 Elsevier Ltd. All rights reserved.