(3S)-3-hydroxy-2,2,5-trimethylhexanal | 1370034-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-hydroxy-2,2,5-trimethylhexanal
• CAS: 1370034-83-5
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: UWCCTRDNAIEEEW-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(苯甲基巯基)乙醛 、 异丁醛 在 L-组氨酸 作用下， 以 水 为溶剂， 生成 (R)-3-hydroxy-2,2,5-trimethylhexanal 、 (3S)-3-hydroxy-2,2,5-trimethylhexanal
  参考文献：
  名称：

  Stereoselectivities of Histidine-Catalyzed Asymmetric Aldol Additions and Contrasts with Proline Catalysis: A Quantum Mechanical Analysis

  摘要：

  Quantum mechanical calculations reveal the origin of diastereo- and enantioselectivities of aldol reactions between aldehydes catalyzed by histidine, and differences between related reactions catalyzed by proline. A stereochemical model that explains both the sense and the high levels of the experimentally observed stereoselectivity is proposed. The computations suggest that both the imidazolium and the carboxylic acid functionalities of histidine are viable hydrogen-bond donors that can stabilize the cyclic aldolization transition state. The stereoselectivity is proposed to arise from minimization of gauche interactions around the forming C-C bond.

  DOI：

  10.1021/ja2118392

文献信息

• Histidine-Catalyzed Asymmetric Aldol Addition of Enolizable Aldehydes: Insights into its Mechanism
  作者：Ulf Scheffler、Rainer Mahrwald

  DOI：10.1021/jo202558f

  日期：2012.3.2

  Extensive studies of asymmetric cross-aldol addition between enolizable aldehydes are described and provide a deeper insight into histidine-catalyzed aldol additions. In particular, aspects of enantio- as well as diastereoselectivity of these reactions are discussed. Rules and predictions of configurative outcome are explained by using different transition-state models. These discussions are confirmed

  描述了可烯化醛之间不对称交叉羟醛加成的广泛研究，并为组氨酸催化的羟醛加成提供了更深入的了解。特别是，讨论了这些反应的对映选择性和非对映选择性。通过使用不同的过渡状态模型来解释配置结果的规则和预测。这些讨论已通过大量的计算得到证实。