2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide | 152529-37-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide
• 英文别名: N-[(R)-1-Ethyl-2-hydroxyethyl]trifluoroacetamide；2,2,2-trifluoro-N-[(2R)-1-hydroxybutan-2-yl]acetamide
• CAS: 152529-37-8
• 化学式: C₆H₁₀F₃NO₂
• 分子量: 185.146
• InChiKey: DPTJDRDWPOSORG-SCSAIBSYSA-N

物化性质

• 熔点：
  74-77 °C
• 沸点：
  245.0±40.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-Phenyl-nonanoic 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-氨基丁醇 、 三氟乙酸乙酯 以 乙腈 为溶剂， 以100%的产率得到2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide
  参考文献：
  名称：

  Chirality-directed organogel formation

  摘要：

  New low molecular mass enantiopure organogelators (1R,4R)-1, (S)-2, (R)-3 and (R)-4 were found; racemates (R,S)-3 and (R,S)-4 have only a moderate gelating power, whereas (R,S)-1 and (R,S)-2 do not show gelating properties at all.

  DOI：

  10.1070/mc2005v015n04abeh002136

文献信息

• Efimov; Buryakova; Choob, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 9, p. 618 - 630
  作者：Efimov、Buryakova、Choob、Chakhmakhcheva

  DOI：——

  日期：——
• Chirality-directed organogel formation
  作者：Remir G. Kostyanovsky、Denis A. Lenev、Oleg N. Krutius、Andrey A. Stankevich

  DOI：10.1070/mc2005v015n04abeh002136

  日期：2005.1

  New low molecular mass enantiopure organogelators (1R,4R)-1, (S)-2, (R)-3 and (R)-4 were found; racemates (R,S)-3 and (R,S)-4 have only a moderate gelating power, whereas (R,S)-1 and (R,S)-2 do not show gelating properties at all.
• 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.