(3R,4R)-3,4-dihydroxy-4-(thiophen-2-yl)butan-2-one | 1280627-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R)-3,4-dihydroxy-4-(thiophen-2-yl)butan-2-one
• 英文别名: (3R,4R)-3,4-dihydroxy-4-thiophen-2-ylbutan-2-one
• CAS: 1280627-60-2
• 化学式: C₈H₁₀O₃S
• 分子量: 186.232
• InChiKey: IGRSBLNSJJCYEW-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 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：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 羟基丙酮 在 1-(4-{(2S)-2-amino-2-[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-(R)-1-methyl-ethoxycarbonyl}-butyl)-3-methyl-3H-imidazol-1-ium hexafluorophosphates 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (3S,4R)-3,4-dihydroxy-4-(thiophen-2-yl)butan-2-one 、 (3R,4R)-3,4-dihydroxy-4-(thiophen-2-yl)butan-2-one
  参考文献：
  名称：

  (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions

  摘要：

  Chiral ionic liquids containing (S)- or (R)-threonine amide and alpha,alpha-(S)-diphenylvalinol units were synthesized In the presence of the (S)-threonine-derived catalyst reactions between ketones with secondary carbon atom(s) at the alpha-position with respect to the carbonyl group and aromatic (heteroaromatic) aldehydes afforded the corresponding syn-aldols in high yields (up to 99%) and with high diastereo-(syn/anti up to 97:3) and enantioselectivity (up to 99% ee), which was maintained over three reaction cycles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.017

文献信息

• Enantioselective organocatalyzed functionalization of benzothiophene and thiophenecarbaldehyde derivatives
  作者：Francesco Secci、Enzo Cadoni、Claudia Fattuoni、Angelo Frongia、Giuseppe Bruno、Francesco Nicolò

  DOI：10.1016/j.tet.2012.04.008

  日期：2012.6

  study on the enantioselective organocatalyzed cross-aldol reaction of 1-benzothiophene and thiophenecarbaldehydes with different ketones. The reactions were conducted at 0 °C or room temperature to afford the corresponding adducts in high yields and good to excellent ee using different organocatalysts. Interestingly, using (S)-pyrrolidine tetrazole and acetoxyacetone an inversion of the aldol regiochemistry

  在本文中，我们报告了对1-苯并噻吩和噻吩甲醛与不同酮的对映选择性有机催化的交叉羟醛反应。该反应在0℃或室温下进行，以使用不同的有机催化剂以高收率和良好至优异的ee提供相应的加合物。有趣的是，使用（S）-吡咯烷四唑和乙酰氧基丙酮观察到羟醛的区域化学反转。
• Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds
  作者：Ling-Yu Li、Da-Cheng Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2015.01.061

  日期：2015.3

  The catalytic promiscuity of pepsin from porcine gastric mucous was observed in catalysis of the direct asymmetric aldol reactions of aromatic aldehydes with acetones, which were substituted by hydroxy-, dihydroxy-, methoxy- and benzyloxy- for the synthesis of diol compounds in acetonitrile. This biocatalysis was also applicable to the aldol reactions of cyclic or hetereocyclic ketones with aromatic

  在催化芳香族醛与丙酮直接不对称醛醇缩合反应的催化过程中，观察到了胃蛋白酶对胃蛋白酶的混杂作用，丙酮醛被羟基，二羟基，甲氧基和苄氧基所取代，从而在乙腈中合成二醇化合物。该生物催化也适用于环状或杂环酮与芳族醛的醛醇缩合反应。获得了高达87％的产率，高达> 99/1 dr的非对映选择性和高达75％ee的对映选择性。
• (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions
  作者：Natalia A. Larionova、Alexandr S. Kucherenko、Dmitry E. Siyutkin、Sergei G. Zlotin

  DOI：10.1016/j.tet.2011.01.017

  日期：2011.3

  Chiral ionic liquids containing (S)- or (R)-threonine amide and alpha,alpha-(S)-diphenylvalinol units were synthesized In the presence of the (S)-threonine-derived catalyst reactions between ketones with secondary carbon atom(s) at the alpha-position with respect to the carbonyl group and aromatic (heteroaromatic) aldehydes afforded the corresponding syn-aldols in high yields (up to 99%) and with high diastereo-(syn/anti up to 97:3) and enantioselectivity (up to 99% ee), which was maintained over three reaction cycles. (C) 2011 Elsevier Ltd. All rights reserved.