(3R)-3-[(S)-hydroxy-(p-cyanophenyl)methyl]tetrahydrothiopyran-4-one

• 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: (3R)-3-[(S)-hydroxy-(p-cyanophenyl)methyl]tetrahydrothiopyran-4-one
• 英文别名: 3-(1-hydroxy-1-(4-cyanophenyl)methyl)-tetrahydrothiopyran-4-one；4-[(S)-hydroxy-[(3R)-4-oxothian-3-yl]methyl]benzonitrile
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: KEMFEKQECPCCKD-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢噻喃-4-酮 、 4-氰基苯甲醛 在 N-{(1S,2S)-2-[4-Me-C₆H₄CONH]-1,2-Ph₂-ethyl}-L-prolinamide 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(3R)-3-[(S)-hydroxy-(p-cyanophenyl)methyl]tetrahydrothiopyran-4-one
  参考文献：
  名称：

  立体和电子可调和双功能有机催化剂：环酮与醛的不对称羟醛反应的设计和应用

  摘要：

  在杂环酮的直接醛醇缩合反应中，已经开发并评估了可立体和电子可调的双功能有机催化剂。具有不同取代基的催化剂对类似的底物显示出不同的催化效率，表明微调两个NH基团中氢键强度的重要性。反应全部以良好至高收率进行，并且具有从90％至> 99％ee的优异对映选择性。在大多数情况下，抗羟醛加合物的非对映选择性高，为96/4至99/1。

  DOI：

  10.1021/jo0615089

文献信息

• Highly stereoselective direct aldol reactions catalyzed by (S)-NOBIN-l-prolinamide
  作者：Alessio Russo、Giovanna Botta、Alessandra Lattanzi

  DOI：10.1016/j.tet.2007.09.027

  日期：2007.11

  (S)-NOBIN-L-prolinamide was employed as organocatalyst in the direct aldol reactions of different ketones and aromatic aldehydes using dioxane as solvent and in the presence of water as additive. Acetone led to the aldol products in up to 93% ee, while cyclic ketones furnished the anti-aldols in moderate to high yield, excellent diastereoselectivity (up to > 99/< 1 anti/syn ratio) and high ee (up to 95%). (c) 2007 Elsevier Ltd. All rights reserved.
• Ficin-catalyzed asymmetric aldol reactions of heterocyclic ketones with aldehydes
  作者：Jian-Ping Fu、Na Gao、Yang Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.molcatb.2013.06.016

  日期：2013.12

  Ficin from fig tree latex displayed a promiscuous activity to catalyze the direct asymmetric aldol reactions of heterocyclic ketones with aromatic aldehydes. Ficin showed good substrate adaptability to different heterocyclic ketones containing nitrogen, oxygen or sulfur. The enantioselectivities up to 81% ee and diastereoselectivities up to 86:14 (anti/syn) were achieved under the optimized reaction conditions. (C) 2013 Elsevier B.V. All rights reserved.
• Sterically and Electronically Tunable and Bifunctional Organocatalysts:  Design and Application in Asymmetric Aldol Reaction of Cyclic Ketones with Aldehydes
  作者：Jia-Rong Chen、Xin-Yong Li、Xiao-Ning Xing、Wen-Jing Xiao

  DOI：10.1021/jo0615089

  日期：2006.10.1

  tunable and bifunctional organocatalysts have been developed and evaluated in the direct aldol reaction of heterocyclic ketones. Catalysts with different substituents showed variable catalytic efficiency for analogous substrates, indicating the importance of fine-tuning the strength of the hydrogen bonding in the two NH groups. The reactions all proceeded in good to high yield and with excellent enantioselectivities

  在杂环酮的直接醛醇缩合反应中，已经开发并评估了可立体和电子可调的双功能有机催化剂。具有不同取代基的催化剂对类似的底物显示出不同的催化效率，表明微调两个NH基团中氢键强度的重要性。反应全部以良好至高收率进行，并且具有从90％至> 99％ee的优异对映选择性。在大多数情况下，抗羟醛加合物的非对映选择性高，为96/4至99/1。