(3R,4S)-3-fluoro-4-hydroxy-4-(4-nitrophenyl)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-fluoro-4-hydroxy-4-(4-nitrophenyl)butan-2-one
• 化学式: C₁₀H₁₀FNO₄
• 分子量: 227.192
• InChiKey: AMQJIRCRERASBT-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氟代丙酮 、 对硝基苯甲醛 在 L-Leu-NH[(S)-1-OH-1,1-Ph₂-3-Me-butan-2-yl] 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (3S,4R)-3-fluoro-4-hydroxy-4-(4-nitrophenyl)butan-2-one 、 (3R,4S)-3-fluoro-4-hydroxy-4-(4-nitrophenyl)butan-2-one 、 4-(4'-nitrophenyl)-3-fluoro-4-hydroxy-2-butanone
  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

• Stereoselective Synthesis of vic-Halohydrins via l-tert-Leucine-Catalyzed syn-Selective Aldol Reaction
  作者：Takashi Itoh、Atsushi Umehara、Takuya Kanemitsu、Kazuhiro Nagata

  DOI：10.1055/s-0031-1290316

  日期：2012.2

  for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones with high syn selectivity (syn/anti = 16:1) and enantioselectivity (up to 95% ee). aldol reaction - amino acids - asymmetric synthesis - chloroacetone - organocatalysis

  升-叔-亮氨酸被认为是为氯丙酮的不对称醛醇缩合反应的有效有机催化剂。vic-卤代醇的立体选择性合成具有出色的区域选择性（> 99％），可生成具有高syn选择性（syn / anti = 16：1）和对映选择性（高达95％ee）的α-氯-β-羟基酮。 Aldol反应-氨基酸-不对称合成-氯丙酮-有机催化
• 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.