(3S,4S)-3-fluoro-4-hydroxy-5-methyl-6-(2'-methyl-thiazol-4'-yl)-hex-5-en-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3S,4S)-3-fluoro-4-hydroxy-5-methyl-6-(2'-methyl-thiazol-4'-yl)-hex-5-en-2-one
• 英文别名: (E,3S,4S)-3-fluoro-4-hydroxy-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)hex-5-en-2-one
• 化学式: C₁₁H₁₄FNO₂S
• 分子量: 243.302
• InChiKey: NBUPPINTVZZGKL-MRUFAENASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氟代丙酮 、 (2E)-2-甲基-3-(2-甲基-1,3-噻唑-4-基)丙烯醛 在 L-脯氨醇 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-1-fluoro-4-hydroxy-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)hex-5-en-2-one 、 (3S,4S)-3-fluoro-4-hydroxy-5-methyl-6-(2'-methyl-thiazol-4'-yl)-hex-5-en-2-one 、 (3R,4R)-3-fluoro-4-hydroxy-5-methyl-6-(2'-methyl-thiazol-4'-yl)-hex-5-en-2-one 、 syn-3-fluoro-4-hydroxy-5-methyl-6-(2'-methyl-thiazol-4'-yl)-hex-5-en-2-one
  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.