(R)-3-(1-hydroxy-3-oxobutyl)benzonitrile | 1279128-93-6

• 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)-3-(1-hydroxy-3-oxobutyl)benzonitrile
• 英文别名: 3-((R)-1-hydroxy-3-oxobutyl)benzonitrile；3-[(1R)-1-hydroxy-3-oxobutyl]benzonitrile
• CAS: 1279128-93-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: MGDZBHOJCNYTAP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氰基苯甲醛 、 丙酮 在 (S)-di-tert-butyl 2-{3-[(1S,2S)-1,2-diphenyl-2-[(S)-(pyrrolidine-2-carboxamido)]ethyl]thioureido}succinate 、 对硝基苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到(R)-3-(1-hydroxy-3-oxobutyl)benzonitrile
  参考文献：
  名称：

  A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

  摘要：

  一种以(S)-脯氨酸、(1S,2S)-二苯基乙二胺和(S)-天冬氨酸二叔丁酯为结构单元的三肽类脯氨酰胺-硫脲催化剂能以高产率和高立体选择性（高达 99 : 1 dr 和 99% ee）提供酮与芳香醛反应的产物。二胺单元的两个手性中心都是必不可少的，而源自胺的硫脲氢和酰胺氢则对催化剂的效率起着主导作用。

  DOI：

  10.1039/c2ob25693b

文献信息

• Prolinamides Bearing Thiourea Groups as Catalysts for Asymmetric Aldol Reactions
  作者：Stamatis Fotaras、Christoforos G. Kokotos、Evaggelia Tsandi、George Kokotos

  DOI：10.1002/ejoc.201001417

  日期：2011.3

  based on α-amino acid amides (proline, valine, and threonine) and chiral diamines bearing thiourea groups were synthesized and their activities for aldol reactions were studied. The catalyst based on (S)-proline and (1S,2S)-diphenylethylenediamine proved to be an excellent catalyst, providing the products of reactions between ketones and aromatic aldehydes in high to quantitative yields and with high

  合成了基于α-氨基酸酰胺（脯氨酸、缬氨酸和苏氨酸）和带有硫脲基团的手性二胺的有机催化剂，并研究了它们对羟醛反应的活性。基于 (S)-脯氨酸和 (1S,2S)-二苯基乙二胺的催化剂被证明是一种极好的催化剂，以高到定量的收率和高立体选择性（高达 98:2 dr和 99% ee）。酸添加剂（4-硝基苯甲酸）的存在对产率和对映选择性都有相当大的影响。
• A novel trifunctional organocatalyst for the asymmetric aldol reaction: a facile enantioselective synthesis of β-hydroxyketones
  作者：B.V. Subba Reddy、K. Bhavani、A. Raju、J.S. Yadav

  DOI：10.1016/j.tetasy.2011.05.001

  日期：2011.4

  A new L-prolinamide trifunctional catalyst has been developed for the enantioselective aldol reaction of various aromatic and aliphatic aldehydes with acetone. This method provides high yields of beta-hydroxyketones (up to 90%) with good enantioselectivity (up to 92%) at a low catalyst loading (10 mol %). (C) 2011 Elsevier Ltd. All rights reserved.
• A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst
  作者：Stamatis Fotaras、Christoforos G. Kokotos、George Kokotos

  DOI：10.1039/c2ob25693b

  日期：——

  A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99 : 1 dr and 99% ee). Both the chiral centers of the diamine unit are essential, while the thiourea hydrogen originating from the amine and the amide hydrogen play a predominant role for the catalyst efficiency.

  一种以(S)-脯氨酸、(1S,2S)-二苯基乙二胺和(S)-天冬氨酸二叔丁酯为结构单元的三肽类脯氨酰胺-硫脲催化剂能以高产率和高立体选择性（高达 99 : 1 dr 和 99% ee）提供酮与芳香醛反应的产物。二胺单元的两个手性中心都是必不可少的，而源自胺的硫脲氢和酰胺氢则对催化剂的效率起着主导作用。