(S)-2-[(R)-1-hydroxy-2-oxo-2-phenylethyl]cyclohexanone | 1261038-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-[(R)-1-hydroxy-2-oxo-2-phenylethyl]cyclohexanone
• 英文别名: 2-(1-hydroxy-2-oxo-2-phenylethyl)cyclohexanone；(2S)-2-[(1R)-1-hydroxy-2-oxo-2-phenylethyl]cyclohexan-1-one
• CAS: 1261038-91-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: VYRWRVCALJKXCU-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯基丙醇水合物 、 1-(dimethylsilyloxy)cyclohexene 在 calcium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (S)-2-[(R)-1-hydroxy-2-oxo-2-phenylethyl]cyclohexanone 、 (+/-)-(2S,1S)-2-(1-hydroxy-2-phenyl-2-oxoethyl)cyclohexanone
  参考文献：
  名称：

  Lewis Base-Promoted Aldol Reaction of Dimethylsilyl Enolates in Aqueous Dimethylformamide:  Use of Calcium Chloride as a Lewis Base Catalyst

  摘要：

  In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields. The catalytic activities of various metal and tetrabutylammonium salts have revealed that CaCl2 works as a Lewis base catalyst to activate DMS enolates. The CaCl2-promoted reaction proceeded even in the presence of water or in pure water. This catalytic system was applicable to the aldol reaction with aqueous aldehydes such as formalin.

  DOI：

  10.1021/ja017218l

文献信息

• Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxyindolin-2-ones
  作者：Qunsheng Guo、Mayur Bhanushali、Cong-Gui Zhao

  DOI：10.1002/anie.201004161

  日期：2010.12.3

  New catalysis mechanism! The asymmetric aldol reaction of unactivated ketones and activated carbonyl compounds is realized with a quinidine‐derived thiourea catalyst (see scheme), and involves an enolate mechanism instead of the widely used enamine mechanism. With isatins as the substrate, the reaction can be applied to the enantioselective synthesis of biologically active 3‐hydroxyindolin‐2‐ones.

  新的催化机制！未活化的酮和活化的羰基化合物的不对称醛醇反应是通过奎尼丁衍生的硫脲催化剂实现的（见方案），并且涉及烯醇机制而不是广泛使用的烯胺机制。以靛红为底物，该反应可用于对映选择性合成具有生物活性的 3-羟基吲哚-2-酮。
• Chitosan Aerogel Beads as a Heterogeneous Organocatalyst for the Asymmetric Aldol Reaction in the Presence of Water: An Assessment of the Effect of Additives
  作者：Claudio Gioia、Alfredo Ricci、Luca Bernardi、Khadidja Bourahla、Nathalie Tanchoux、Mike Robitzer、Françoise Quignard

  DOI：10.1002/ejoc.201201187

  日期：2013.1

  The catalytic properties of chitosan aerogel for the direct asymmetric aldol reaction in water assisted by various surfactants and acid co-catalysts have been evaluated by employing a range of donor and acceptor systems. A beneficial effect on both the yields and nantioselectivities was observed, and the combination of surfactants and acid co-catalysts has proven particularly useful in the case of

  壳聚糖气凝胶在各种表面活性剂和酸助催化剂的辅助下，在水中直接不对称醛醇反应的催化性能已经通过使用一系列供体和受体系统进行了评估。观察到对产率和纳米选择性的有益影响，并且已证明表面活性剂和酸助催化剂的组合在杂环酮供体的情况下特别有用。
• Organocatalyzed Asymmetric Aldol Reactions of Ketones and β,γ-Unsaturated α-Ketoesters and Phenylglyoxal Hydrates
  作者：Swapna Konda、Qun-Sheng Guo、Manabu Abe、Huicai Huang、Hadi Arman、John C.-G. Zhao

  DOI：10.1021/jo502254e

  日期：2015.1.16

  Enantioselective aldol reactions of acetophenone with beta,gamma-unsaturated a-ketoesters and cyclic ketones with phenylglyoxal hydrates were realized with cinchona alkaloid-derived thiourea catalysts. The corresponding aldol products were obtained in high yields and good to excellent diastereoselectivities and enantioselectivities (up to 95% ee).