(3R)-3-[(S)-hydroxy-(o-nitrophenyl)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-(o-nitrophenyl)methyl]tetrahydrothiopyran-4-one
• 英文别名: 3-(1-hydroxy-1-(2-nitrophenyl)methyl)-tetrahydrothiopyran-4-one；(3R)-3-[(S)-hydroxy-(2-nitrophenyl)methyl]thian-4-one
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: ASXMHMMJVMFZQN-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢噻喃-4-酮 、 邻硝基苯甲醛 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93%的产率得到(3R)-3-[(S)-hydroxy-(o-nitrophenyl)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

• An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions
  作者：Xue-Wei Liu、Thanh Nguyen Le、Yunpeng Lu、Yongjun Xiao、Jimei Ma、Xingwei Li

  DOI：10.1039/b811581h

  日期：——

  Chiral pyrrolidine-based phosphinyl oxides were synthesized and their performance as organocatalysts for asymmetric direct aldol reactions was evaluated. High enantioselectivities and diastereoselectivies were achieved for a range of cyclic ketones and aromatic aldehydes.

  合成了手性吡咯烷基氧化膦，并评估了它们作为有机催化剂用于不对称直接羟醛反应的性能。对于一系列环酮和芳族醛，实现了高对映选择性和非对映选择性。
• Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts
  作者：Debarshi Sinha、Tanmay Mandal、Sanjib Gogoi、Joshua J. Goldman、John Cong-gui Zhao

  DOI：10.1002/cjoc.201200639

  日期：2012.9.27

  are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for catalyzed asymmetric aldol reaction. Depending on structure of the aldehyde substrates, the corresponding aldol products may be obtained in mediocre to excellent ee values (up to 92% ee) with moderate diastereoselectivities

  氨基酸和金鸡纳生物碱衍生物等预催化剂模块的自组装可直接形成所需的有机催化剂，而无需任何合成。这些模块化设计的有机催化剂（MDO）可用于催化不对称的羟醛反应。取决于醛底物的结构，可以以中等的非对映选择性（高达79:21 dr）以中等至优异的ee值（高达92％ee）获得相应的羟醛产物。
• 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.
• 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。