4'-acetamidobenzyl (2S,3S)-3-fluoro-2-hydroxy-4-ketovalerate

• 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: 4'-acetamidobenzyl (2S,3S)-3-fluoro-2-hydroxy-4-ketovalerate
• 英文别名: (4-acetamidophenyl)methyl (2S,3S)-3-fluoro-2-hydroxy-4-oxopentanoate
• 化学式: C₁₄H₁₆FNO₅
• 分子量: 297.283
• InChiKey: NGXKMNOBWFTHHW-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氟代丙酮 、 (4-Acetamidophenyl)methyl 2-oxoacetate 在 L-脯氨醇 作用下， 以 二甲基亚砜 为溶剂， 生成 (4-Acetamidophenyl)methyl 5-fluoro-2-hydroxy-4-oxopentanoate 、 4'-acetamidobenzyl (2S,3S)-3-fluoro-2-hydroxy-4-ketovalerate 、 4'-acetamidobenzyl (2R,3R)-3-fluoro-2-hydroxy-4-ketovalerate 、 4'-acetamidobenzyl syn-3-fluoro-2-hydroxy-4-ketovalerate
  参考文献：
  名称：

  Amino alcohol catalyzed direct asymmetric aldol reactions: enantioselective synthesis of anti -α-fluoro-β-hydroxy ketones

  摘要：

  Prolinol but not proline-(a recently established catalyst of simple intermolecular aldol reactions) was found to be an efficient catalyst for fluoroaldol reactions providing anti-alpha-fluoro-beta-hydroxy ketones with good regio-, diasterio-, and enantio-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.107

文献信息

• Amino alcohol catalyzed direct asymmetric aldol reactions: enantioselective synthesis of anti -α-fluoro-β-hydroxy ketones
  作者：Guofu Zhong、Junhua Fan、Carlos F. Barbas

  DOI：10.1016/j.tetlet.2004.05.107

  日期：2004.7

  Prolinol but not proline-(a recently established catalyst of simple intermolecular aldol reactions) was found to be an efficient catalyst for fluoroaldol reactions providing anti-alpha-fluoro-beta-hydroxy ketones with good regio-, diasterio-, and enantio-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.