(3R,4R)-4-(o-nitrophenyl)-1,3,4-trihydroxy-1,3-O-isopropyliden-butan-2-one | 1007839-82-8

• 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,4R)-4-(o-nitrophenyl)-1,3,4-trihydroxy-1,3-O-isopropyliden-butan-2-one
• 英文别名: (4R)-4-[(R)-hydroxy-(2-nitrophenyl)methyl]-2,2-dimethyl-1,3-dioxan-5-one
• CAS: 1007839-82-8
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: NKCXFZBXDYJJIV-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2-二甲基-1,3-二恶烷-5-酮 、 邻硝基苯甲醛 在 三氟甲磺酸 、 chiral diamine 、 间硝基苯甲酸 作用下， 反应 24.0h， 生成 4-(o-nitrophenyl)-1,3,4-trihydroxy-1,3-O-isopropyliden-butan-2-one 、 (3S,4S)-4-(o-nitrophenyl)-1,3,4-trihydroxy-1,3-O-isopropyliden-butan-2-one 、 (3R,4R)-4-(o-nitrophenyl)-1,3,4-trihydroxy-1,3-O-isopropyliden-butan-2-one
  参考文献：
  名称：

  Highly Enantioselective Direct syn- and anti-Aldol Reactions of Dihydroxyacetones Catalyzed by Chiral Primary Amine Catalysts

  摘要：

  We present herein simple primary-tertiary diamine-Bronsted acid conjugates that catalyze both syn- and anti-adol reactions of dihydroxyacetones (DHAs) with high diastereoselectivities and enantioselectivities. This type of organocatalysts functionally mimics all four DHA aldolases, namely L-fuculose-1-phosphate aldolase, D-tagatose-1,6-diphosphate aldolase, D-fructose-1,6-diphosphate aldolase, and L-rhamnulose-1-phosphate aldolase.

  DOI：

  10.1021/ol703023t

文献信息

• Highly Enantioselective Direct <i>syn</i>- and <i>anti</i>-Aldol Reactions of Dihydroxyacetones Catalyzed by Chiral Primary Amine Catalysts
  作者：Sanzhong Luo、Hui Xu、Long Zhang、Jiuyuan Li、Jin-Pei Cheng

  DOI：10.1021/ol703023t

  日期：2008.2.1

  We present herein simple primary-tertiary diamine-Bronsted acid conjugates that catalyze both syn- and anti-adol reactions of dihydroxyacetones (DHAs) with high diastereoselectivities and enantioselectivities. This type of organocatalysts functionally mimics all four DHA aldolases, namely L-fuculose-1-phosphate aldolase, D-tagatose-1,6-diphosphate aldolase, D-fructose-1,6-diphosphate aldolase, and L-rhamnulose-1-phosphate aldolase.
• Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water
  作者：Elisa G. Doyagüez、Alfonso Fernández-Mayoralas

  DOI：10.1016/j.tet.2012.06.089

  日期：2012.9

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.