(3R,4S)-3,4-dihydroxy-4-(3-chloro-4-fluorophenyl)butan-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)-3,4-dihydroxy-4-(3-chloro-4-fluorophenyl)butan-2-one
• 英文别名: (3R,4S)-4-(3-chloro-4-fluorophenyl)-3,4-dihydroxybutan-2-one
• 化学式: C₁₀H₁₀ClFO₃
• 分子量: 232.639
• InChiKey: MYURAPGNTRBCKL-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 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：

  3-氯-4-氟苯甲醛 、 羟基丙酮 在 (1S,2S)-N'-methyl-N'-((S)-1-phenylethyl)cyclohexane-1,2-diamine 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到(3R,4S)-3,4-dihydroxy-4-(3-chloro-4-fluorophenyl)butan-2-one
  参考文献：
  名称：

  在水介质中高度对映选择性的有机催化合成和反羟醛反应

  摘要：

  Abstractmagnified imageWe have synthesized chiral diamines that efficiently catalyze the syn‐ and anti‐aldol reactions in aqueous medium with high diastereo‐ and enantioselectivities. The product, thus obtained, was further reduced selectively to give syn‐configured 1,2,3‐triol, an important subunit present in various monosaccharides and natural products such as (+)‐boronolide.

  DOI：

  10.1002/adsc.200900122

文献信息

• 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.