(3R,4S)-4-(2-fluorophenyl)-3,4-dihydroxybutan-2-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,4S)-4-(2-fluorophenyl)-3,4-dihydroxybutan-2-one
• 化学式: C₁₀H₁₁FO₃
• 分子量: 198.194
• InChiKey: UMJABKSVFUHILW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氟苯甲醛 、 羟基丙酮 在 L-Leu-NH[(S)-1-OH-1,1-(3,5-(CF₃)2C₆H₃)2-3-Me-butan-2-yl] 作用下， 以 xylene 为溶剂， 反应 36.0h， 生成 (3S,4R)-4-(2-fluorophenyl)-3,4-dihydroxybutan-2-one 、 (3R,4S)-4-(2-fluorophenyl)-3,4-dihydroxybutan-2-one 、 4-(2-fluorophenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  Design of Organocatalysts for Asymmetric Direct Syn-Aldol Reactions

  摘要：

  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.

  DOI：

  10.1021/ol701798x

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。
• 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.