methyl 4-((1S,2R)-1,2-dihydroxy-3-oxobutyl)benzoate

• 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: methyl 4-((1S,2R)-1,2-dihydroxy-3-oxobutyl)benzoate
• 英文别名: methyl 4-[(1S,2R)-1,2-dihydroxy-3-oxobutyl]benzoate
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: PCCFGCJTNZQAKH-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟基丙酮 、 对甲酰基苯甲酸甲酯 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 methyl 4-((1S,2R)-1,2-dihydroxy-3-oxobutyl)benzoate 、
  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

• An Enantioselective Recyclable Polystyrene-Supported Threonine-Derived Organocatalyst for Aldol Reactions
  作者：Andrea H. Henseler、Carles Ayats、Miquel A. Pericàs

  DOI：10.1002/adsc.201400033

  日期：2014.5.26

  amino acids covalently supported onto polystyrene through alkyne–azide cycloaddition reactions has been synthesized and evaluated as catalysts in asymmetric aldol reactions. A polymer‐supported threonine behaves as an easily recyclable, highly reactive and stereoselective (up to 99% ee) catalyst in the aldol reaction of both cyclic and acyclic ketone donors with aromatic aldehydes in aqueous environments

  合成了一系列通过炔-叠氮化物环加成反应共价负载在聚苯乙烯上的伯氨基酸，并作为不对称羟醛反应的催化剂进行了评估。在水性环境中，环状和非环状酮供体与芳族醛的醛醇缩合反应中，聚合物负载的苏氨酸可作为易于回收，高反应性和立体选择性（高达99％ee）的催化剂。而环状酮与反应反非对映选择性，顺式加成物主要与无环的基材而获得。苏氨酸杂化催化剂已用于对映纯的醛醇缩醛产物的小型文库的顺序合成。
• Design of Organocatalysts for Asymmetric Direct Syn-Aldol Reactions
  作者：Xiao-Ying Xu、Yan-Zhao Wang、Liu-Zhu Gong

  DOI：10.1021/ol701798x

  日期：2007.10.1

  Two new organocatalysts 3a and 3b, derived from L-leucine and (S)-beta-amino alcohols that were prepared from L-valine, were designed and afforded the direct syn-aldol reactions of a wide scope of aldehydes with various ketones with an excellent diastereomeric ratio of up to >20/1 and enantioselectivities of up to 99% ee.
• (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.