(R)-4-cyclopropyl-1,1,1-trifluoro-2-(4-methoxyphenyl)but-3-yn-2-amine | 1269535-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-4-cyclopropyl-1,1,1-trifluoro-2-(4-methoxyphenyl)but-3-yn-2-amine
• 英文别名: (2R)-4-cyclopropyl-1,1,1-trifluoro-2-(4-methoxyphenyl)but-3-yn-2-amine
• CAS: 1269535-55-8
• 化学式: C₁₄H₁₄F₃NO
• 分子量: 269.266
• InChiKey: CRCAWOSURQWRDF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,2-三氟-4-甲氧基乙酰苯 在 titanium(IV) isopropylate 、 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 为溶剂， 反应 2.0h， 生成 (R)-4-cyclopropyl-1,1,1-trifluoro-2-(4-methoxyphenyl)but-3-yn-2-amine
  参考文献：
  名称：

  Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines

  摘要：

  A convenient and practical method for the preparation of enantiomerically pure alpha-trifluoromethylated alpha-propargylamines is described. A range of enantiopure alpha-trifluoromethylated alpha-propargyl sulfinamides were obtained by the addition of lithium acetylides generated in situ with n-BuLi and terminal alkynes to diverse chiral CF3-substituted (S)-N-tert-butanesulfinyl ketimines in moderate to excellent yields (56-97%) and with uniformly excellent diastereoselectivities (>99:1) by using Ti((OPr)-Pr-i)(4) as the catalyst and THF as the polar solvent. Enantiomerically pure alpha-trifluoromethylated alpha,alpha-dibranched propargyl amines were then readily obtained in excellent yields (87-97%) by acidic cleavage of the tert-butanesulfinyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.028

文献信息

• Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines
  作者：Hengqiao Xiao、Yangen Huang、Feng-Ling Qing

  DOI：10.1016/j.tetasy.2010.11.028

  日期：2010.12

  A convenient and practical method for the preparation of enantiomerically pure alpha-trifluoromethylated alpha-propargylamines is described. A range of enantiopure alpha-trifluoromethylated alpha-propargyl sulfinamides were obtained by the addition of lithium acetylides generated in situ with n-BuLi and terminal alkynes to diverse chiral CF3-substituted (S)-N-tert-butanesulfinyl ketimines in moderate to excellent yields (56-97%) and with uniformly excellent diastereoselectivities (>99:1) by using Ti((OPr)-Pr-i)(4) as the catalyst and THF as the polar solvent. Enantiomerically pure alpha-trifluoromethylated alpha,alpha-dibranched propargyl amines were then readily obtained in excellent yields (87-97%) by acidic cleavage of the tert-butanesulfinyl group. (C) 2010 Elsevier Ltd. All rights reserved.