(S)-4-(furan-2-yl)-4-hydroxybutan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-(furan-2-yl)-4-hydroxybutan-2-one
• 英文别名: (4S)-4-(furan-2-yl)-4-hydroxybutan-2-one
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: HMWQAFHFWNPRTN-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠醛 、 丙酮 在 C₂₂H₂₈N₂OS 、 苯甲酸 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (R)-4-(furan-2-yl)-4-hydroxybutan-2-one 、 (S)-4-(furan-2-yl)-4-hydroxybutan-2-one
  参考文献：
  名称：

  脯氨酸硫代酰胺衍生物在水性介质中催化的高效直接不对称醛醇反应

  摘要：

  L-脯氨酸硫代酰胺衍生物 1c 由易得的天然氨基酸 L-脯氨酸和 L-缬氨酸制备，研究了丙酮与各种芳香醛在 0°C 或室温下的直接不对称醛醇反应。在该催化体系中仅使用了 0.1-0.2 mol-% 的衍生物 1c，并且在水性介质中可以实现出色的对映选择性和产率（高达 98% 的产率，>99% ee）。

  DOI：

  10.1002/ejoc.201001115

文献信息

• Efficient asymmetric catalysis of chiral organoaluminum complex for enantioselective ene reactions of aldehydes
  作者：Takashi Ooi、Kohsuke Ohmatsu、Daisuke Uraguchi、Keiji Maruoka

  DOI：10.1016/j.tetlet.2004.04.052

  日期：2004.5

  Chiral organoaluminum complex 1 efficiently catalyzed the asymmetric hetero-ene reaction of commercially available 2-methoxypropene (2) with aldehydes under mild conditions to give the corresponding β-hydroxymethyl ketones 3 in good to excellent chemical yields with high enantiomeric excesses. The asymmetric catalysis of 1 was further applied to the carbonyl addition of methallylsilanes, where exclusive

  手性有机铝络合物1在温和的条件下有效催化了市售的2-甲氧基丙烯（2）与醛的不对称杂烯反应，从而以高至优异的化学收率和较高的对映体过量得到相应的β-羟甲基酮3。将1的不对称催化进一步应用于甲基烯丙基硅烷的羰基加成，其中实现了旋光性烯丙基硅烷5的排他性形成。
• Rational Combination of Two Privileged Chiral Backbones: Highly Efficient Organocatalysts for Asymmetric Direct Aldol Reactions between Aromatic Aldehydes and Acylic Ketones
  作者：Jia-Rong Chen、Xiao-Lei An、Xiao-Yu Zhu、Xu-Fan Wang、Wen-Jing Xiao

  DOI：10.1021/jo800910s

  日期：2008.8.1

  A new class of organocatalysts has been designed by rational combination of proline with cinchona alkaloids. The chiral amine 3a, prepared from l-proline and cinchonidine, has been found to be an efficient catalyst for the direct aldol reactions of acetone or 2-butanone with a wide range of aldehydes (up to 98% ee). The cinchonidine backbone is essential to the reaction efficiency and enantioselectivity

  通过脯氨酸与金鸡纳生物碱的合理结合，已经设计出了一类新的有机催化剂。已经发现由1-脯氨酸和辛可尼定制备的手性胺3a是丙酮或2-丁酮与多种醛（至多98％ee）的直接羟醛直接反应的有效催化剂。辛可尼定骨架对反应效率和对映选择性是必不可少的。
• A Selective Direct Aldol Reaction in Aqueous Media Catalyzed byZinc-Proline
  作者：Ruben Fernandez-Lopez、Jacob Kofoed、Miguel Machuqueiro、Tamis Darbre

  DOI：10.1002/ejoc.200500352

  日期：2005.12

  The Zn–proline complex is shown to catalyze the aldol reaction of acetone and a wide range of arenecarbaldehydes in aqueous media, accepting even deactivated arenecarbaldehydes such as methoxybenzaldehydes in good yields. Enantiomeric excesses of up to 56 % could be obtained with 5 mol-% of the catalyst at room temperature, and up to 66 %

  Zn-脯氨酸配合物可催化丙酮和多种芳烃甲醛在水性介质中的羟醛反应，甚至可以以良好的收率接受失活的芳烃甲醛，例如甲氧基苯甲醛。在室温下使用 5 mol-% 的催化剂可以获得高达 56 % 的对映体过量，高达 66 %
• Highly Enantioselective Direct Asymmetric Aldol Reaction Catalyzed by 4,5-Methano-<i>L</i>-proline
  作者：Yukun Zhang、Jun Zhu、Na Yu、Han Yu

  DOI：10.1002/cjoc.201400732

  日期：2015.2

  The 4,5‐methano‐L‐proline was used as chiral organocatalysts in direct asymmetric aldol reactions. Under the optimal conditions, excellent enantioselectivities (up to 99% ee) were obtained with high chemical yields (up to 95%) for a series of aldehydes using only 5 mol% catalyst loading. To show the practicality of the method, the reaction was tested at a large scale. The reaction was complete in 16

  4,5-甲基-L-脯氨酸在直接不对称羟醛反应中用作手性有机催化剂。在最佳条件下，仅使用5 mol％的催化剂负载量，即可获得一系列醛类的高化学收率（高达95％）的优异对映选择性（高达99％ee）。为了证明该方法的实用性，对该反应进行了大规模测试。该反应在16小时内完成，并且以86％的收率和93％的ee获得了羟醛产物。
• The 4,5-methano-l-proline as a chiral organocatalysts in direct asymmetric aldol reactions
  作者：Na Yu、Sheng Han、Han Yu

  DOI：10.1016/j.tet.2015.04.075

  日期：2015.7

  The 4,5-methano-L-proline was studied for the direct asymmetric aldol reaction of acetone or cyclohexanone with various aromatic and aliphaticaldehydes at -20 degrees C or 0 degrees C. A loading of only 5mol % of derivative la was employed in this catalytic system, and excellent enantioselectivities (up to 99% ee) and yields (up to 98% yield) could be achieved. (C) 2015 Elsevier Ltd. All rights reserved.