(2R)-2-(2,2,2-trifluoroethylamino)butan-1-ol | 152529-38-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-(2,2,2-trifluoroethylamino)butan-1-ol
• CAS: 152529-38-9
• 化学式: C₆H₁₂F₃NO
• 分子量: 171.163
• InChiKey: QYCBTXCQSNFWMT-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-(2,2,2-trifluoroethylamino)butan-1-ol 在 sodium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-Phenyl-heptanoic acid ((R)-1-hydroxymethyl-propyl)-(2,2,2-trifluoro-ethyl)-amide
  参考文献：
  名称：

  Enantioselective Michael additions of Grignard reagents to cinnamamides deriving from N-fluoroalkyl (R)-(−)-2-aminobutan-1-ol. determination of diastereomeric excess by means of 19F NMR

  摘要：

  N-Alkylation of (R)-(-)-2-aminobutan-1-ol 1 (a readily available reagent) with ortho-fluorobenzyl chloride, followed by reaction with cinnamoyl chloride, afforded the cinnamamide (R)-(+)-6. Michael addition of n-alkyl magnesium halides to the latter gave the corresponding adducts (R,R)-8a-e whose diastereomeric excesses were higher than 92% as evidenced by F-19 NMR. Acidic hydrolysis of these adducts yielded the corresponding beta-phenylalkanoic acids (R)-(-)-9a-e.

  DOI：

  10.1016/s0957-4166(00)80345-6
• 作为产物：
  描述：

  2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 10.0h， 以70.5%的产率得到(2R)-2-(2,2,2-trifluoroethylamino)butan-1-ol
  参考文献：
  名称：

  Enantioselective Michael additions of Grignard reagents to cinnamamides deriving from N-fluoroalkyl (R)-(−)-2-aminobutan-1-ol. determination of diastereomeric excess by means of 19F NMR

  摘要：

  N-Alkylation of (R)-(-)-2-aminobutan-1-ol 1 (a readily available reagent) with ortho-fluorobenzyl chloride, followed by reaction with cinnamoyl chloride, afforded the cinnamamide (R)-(+)-6. Michael addition of n-alkyl magnesium halides to the latter gave the corresponding adducts (R,R)-8a-e whose diastereomeric excesses were higher than 92% as evidenced by F-19 NMR. Acidic hydrolysis of these adducts yielded the corresponding beta-phenylalkanoic acids (R)-(-)-9a-e.

  DOI：

  10.1016/s0957-4166(00)80345-6

文献信息

• Enantioselective syntheses of α-phenylalkanamines via intermediate addition of Grignard reagents to chiral hydrazones derived from (R)-(−)-2-aminobutan-1-ol
  作者：Patricia Bataille、Michel Paterne、Eric Brown

  DOI：10.1016/s0957-4166(98)00217-1

  日期：1998.6

  The hydrazine (R)-(−)-28 was obtained in four steps from 2-aminobutan-1-ol (R)-(−)-11, and reacted with benzaldehyde to give the hydrazone (R)-(−)-29. Nucleophilic addition of various alkyl Grignard reagents to the latter yielded the corresponding trisubstituted hydrazines (R,R)-30a–g in 70–89% yields and having d.e.s=100% (1H and 13C NMR). Catalytic hydrogenolysis of these hydrazines afforded the

  从2-氨基丁-1-醇（R）-（-）- 11通过四个步骤获得肼（R）-（-）- 28，并与苯甲醛反应得到the（R）-（-）-。29。向后者亲核添加各种烷基格氏试剂可得到相应的三取代肼（R，R）-30a - g，产率为70-89％，des = 100％（1 H和13 C NMR）。这些肼的催化氢解反应提供了相应的（R）-（+）-α-苯基链烷胺（R）-（+）- 31a – g ee = 90–92％（手性GPC）。
• Enantioselective Michael additions of Grignard reagents to cinnamamides deriving from N-fluoroalkyl (R)-(−)-2-aminobutan-1-ol. determination of diastereomeric excess by means of 19F NMR
  作者：Joël Touet、Christelle Le Grumelec、François Huet、Eric Brown

  DOI：10.1016/s0957-4166(00)80345-6

  日期：1993.7

  N-Alkylation of (R)-(-)-2-aminobutan-1-ol 1 (a readily available reagent) with ortho-fluorobenzyl chloride, followed by reaction with cinnamoyl chloride, afforded the cinnamamide (R)-(+)-6. Michael addition of n-alkyl magnesium halides to the latter gave the corresponding adducts (R,R)-8a-e whose diastereomeric excesses were higher than 92% as evidenced by F-19 NMR. Acidic hydrolysis of these adducts yielded the corresponding beta-phenylalkanoic acids (R)-(-)-9a-e.