(R)-3-chloro-2-methylpropyl trifluoromethanesulfonate | 1443008-32-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-3-chloro-2-methylpropyl trifluoromethanesulfonate
• CAS: 1443008-32-9
• 化学式: C₅H₈ClF₃O₃S
• 分子量: 240.631
• InChiKey: MNQONKQMHJKLIF-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(((E)-2,2-dimethylpropylidene)amino)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N-methylpropanamide 、 (R)-3-chloro-2-methylpropyl trifluoromethanesulfonate 在 lithium chloride 、 lithium diisopropyl amide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.25h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine

  摘要：

  The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.

  DOI：

  10.1021/ol401337p
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (2R)-3-chloro-2-methyl-1-propanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.6h， 以68%的产率得到(R)-3-chloro-2-methylpropyl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine

  摘要：

  The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.

  DOI：

  10.1021/ol401337p