(3S,4R)-3,4-dihydroxy-4-(4-methoxyphenyl)butan-2-one | 1007840-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3S,4R)-3,4-dihydroxy-4-(4-methoxyphenyl)butan-2-one
• CAS: 1007840-06-3
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: OXDBJNMOHNJOBV-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 羟基丙酮 在 三氟甲磺酸 、 chiral diamine 、 间硝基苯甲酸 作用下， 以 正己烷 为溶剂， 反应 36.0h， 生成 (3R,4S)-4-(4-methoxy-phenyl)-3,4-dihydroxybutan-2-one 、 (3S,4R)-3,4-dihydroxy-4-(4-methoxyphenyl)butan-2-one 、 4-(4-methoxy-phenyl)-3,4-dihydroxybutan-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

• Insights into Substituent Effects of Benzaldehyde Derivatives in a Heterogeneous Organocatalyzed Aldol Reaction
  作者：Graziano Di Carmine、Fabio Pesciaioli、Simeng Wang、Arianna Sinibaldi、Giuliana Giorgianni、Christopher M. A. Parlett、Armando Carlone、Carmine D'Agostino

  DOI：10.1002/cctc.202200405

  日期：2022.7.21

  heterogenous organocatalysis is undoubtedly critical to develop new and higher performing catalysts. NMR relaxation techniques provide very useful insights into adsorption effects of the aldehyde partner in an organocatalyzed aldol reaction.

  吸附：了解影响和控制多相有机催化的因素对于开发新的和更高性能的催化剂无疑是至关重要的。核磁共振弛豫技术提供了非常有用的见解，了解醛伴侣在有机催化醛醇反应中的吸附效果。
• 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.