(1S(R),2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-2-fluoropropionamide | 198779-12-3

• 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: (1S(R),2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-2-fluoropropionamide
• 英文别名: (2R)-2-fluoro-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide
• CAS: 198779-12-3
• 化学式: C₁₃H₁₈FNO₂
• 分子量: 239.29
• InChiKey: XKEOAJUHKXYIPJ-JFGNBEQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S(R),2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-2-fluoropropionamide 在 sodium hydroxide 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 4.0h， 以91%的产率得到(R)-α-fluoropropionic acid
  参考文献：
  名称：

  Practical methodology for the asymmetric synthesis of organofluorine compounds

  摘要：

  Pseudoephedrine alpha-fluoroacetamide (1), a nonvolatile, crystalline solid, is alkylated efficiently and with high diastereoselectivity with reactive alkylhalides. The alkylation products can be hydrolyzed under mild basic conditions to form alpha-fluoro carboxylates with high enantiomeric enrichment. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00152-x
• 作为产物：
  描述：

  (1S,2S)-2-甲氨基-1-苯基丙-1-醇 在 正丁基锂 、 六甲基二硅氮烷 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 (1S(R),2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-2-fluoropropionamide
  参考文献：
  名称：

  Practical methodology for the asymmetric synthesis of organofluorine compounds

  摘要：

  Pseudoephedrine alpha-fluoroacetamide (1), a nonvolatile, crystalline solid, is alkylated efficiently and with high diastereoselectivity with reactive alkylhalides. The alkylation products can be hydrolyzed under mild basic conditions to form alpha-fluoro carboxylates with high enantiomeric enrichment. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00152-x

文献信息

• Synthesis of tertiary alkyl fluoride centers by asymmetric CC(F) bond formation
  作者：Andrew G. Myers、Lydia McKinstry、James L. Gleason

  DOI：10.1016/s0040-4039(97)01706-1

  日期：1997.10

  Asymmetric alkylation of pseudoephedrine α-fluoropropionamide (1) affords α-alkylated products efficiently and with excellent stereocontrol at the newly formed tertiary alkyl fluoride center. Mild alkaline hydrolysis of the products provides the corresponding carboxylic acids with high enantiomeric excess.

  伪麻黄碱α-氟丙酰胺（1）的不对称烷基化可高效地提供α-烷基化产物，并在新形成的叔烷基氟化物中心具有出色的立体控制。产物的轻度碱水解提供相应的具有高对映体过量的羧酸。
• Practical methodology for the asymmetric synthesis of organofluorine compounds
  作者：Andrew G. Myers、Lydia McKinstry、Joseph K. Barbay、James L. Gleason

  DOI：10.1016/s0040-4039(98)00152-x

  日期：1998.3

  Pseudoephedrine alpha-fluoroacetamide (1), a nonvolatile, crystalline solid, is alkylated efficiently and with high diastereoselectivity with reactive alkylhalides. The alkylation products can be hydrolyzed under mild basic conditions to form alpha-fluoro carboxylates with high enantiomeric enrichment. (C) 1998 Elsevier Science Ltd. All rights reserved.