(S)-2,2,2-trifluoro-N-(1-hydroxy-3-methylbutan-2-yl)acetamide | 159651-05-5

• 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: (S)-2,2,2-trifluoro-N-(1-hydroxy-3-methylbutan-2-yl)acetamide
• 英文别名: 2,2,2-trifluoro-N-(1-hydroxy-3-methylbutan-2-yl)acetamide；N-trifluoracetyl-L-valinol；(S)-2-(Trifluoroacetylamino)-3-methyl-1-butanol；2,2,2-trifluoro-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]acetamide
• CAS: 159651-05-5
• 化学式: C₇H₁₂F₃NO₂
• 分子量: 199.173
• InChiKey: FQZWCAOSJGKODD-RXMQYKEDSA-N

物化性质

• 沸点：
  254.2±40.0 °C(predicted)
• 密度：
  1.209±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (S)-2,2,2-trifluoro-N-(1-hydroxy-3-methylbutan-2-yl)acetamide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,2-trifluoro-N-(3-methyl-1-oxobutan-2-yl)acetamide
  参考文献：
  名称：

  Autotandem Catalysis with Ruthenium: Remote Hydroesterification of Allylic Amides

  摘要：

  A one-pot tandem sequence involving olefin isomerization and hydroesterification has been developed that enables the incorporation of a C-1-unit at the remote terminal position of allylic amides. Key observations suggest that generation of an active ruthenium hydride, formed by addition of acetic acid, allows both processes to take place under mild conditions in an autotandem catalytic, cascading fashion, which is characterized by the use of a single catalytic entity capable of promoting multiple distinct steps without operator intervention.

  DOI：

  10.1021/ol4034463
• 作为产物：
  描述：

  L-缬氨醇 、 三氟乙酸酐 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-2,2,2-trifluoro-N-(1-hydroxy-3-methylbutan-2-yl)acetamide
  参考文献：
  名称：

  由氨基醇合成新型氟模块化手性配体衍生物及其在对映选择性碳-碳键形成烷基化反应中的应用

  摘要：

  N-三氟酰基β-硫属酰胺和N-全氟酰基β-硫代酰胺配体是通过简单而有效的反应顺序制备的。在丙二酸二甲酯存在下，钯催化外消旋-（E）-1,3-二苯基-2-丙烯基乙酸乙烯酯的烷基化反应中，对这些新的配体进行了评估，对映选择性高达99％。催化后，可以通过液-液萃取容易地回收氟配体，并可以在不损失活性的情况下重复使用。

  DOI：

  10.1016/j.tetasy.2010.05.015

文献信息

• Synthesis of new fluorous modular chiral ligand derivatives from amino alcohols and application in enantioselective carbon–carbon bond-forming alkylation reactions
  作者：Jasquer A. Sehnem、Priscila Milani、Vanessa Nascimento、Leandro H. Andrade、Luciano Dorneles、Antonio L. Braga

  DOI：10.1016/j.tetasy.2010.05.015

  日期：2010.4

  N-Trifluoracyl β-chalcogeno amides and N-perfluoracyl β-thio amide ligands were prepared by a simple and efficient reaction sequence. These new ligands were evaluated in palladium-catalyzed alkylation of rac-(E)-1,3-diphenyl-2-propenyl acetate in the presence of dimethyl malonate and an enantioselectivity of up to 99% was obtained. After catalysis, the fluorous ligand can be easily recovered by liquid–liquid

  N-三氟酰基β-硫属酰胺和N-全氟酰基β-硫代酰胺配体是通过简单而有效的反应顺序制备的。在丙二酸二甲酯存在下，钯催化外消旋-（E）-1,3-二苯基-2-丙烯基乙酸乙烯酯的烷基化反应中，对这些新的配体进行了评估，对映选择性高达99％。催化后，可以通过液-液萃取容易地回收氟配体，并可以在不损失活性的情况下重复使用。
• Improved synthesis of phenylethylamine derivatives by Negishi cross-coupling reactions
  作者：Craig M.L. Goddard、Ahmad Reza Massah、Richard F.W. Jackson

  DOI：10.1016/j.tet.2010.09.074

  日期：2010.11

  Trifluoroacetamido-protected beta-aminoalkylzinc iodides undergo Negishi cross-coupling reaction with aryl iodides in moderate to excellent yields (42-84%) based on the corresponding trifluoroacetamido-protected beta-aminoalkyl iodides employing a catalyst prepared in situ from Pd-2(dba)(3) and SPhos (1 2 M ratio) In general meta- and para-substituted aryl iodides give good results using relatively low levels of catalyst [0 25 mol % Pd-2(dba)(3)] but more hindered ortho-substituted examples require higher catalyst loadings The preparation of trifluoroacetamido-protected beta-aminoalkyl iodides is straightforward and the intermediates are significantly more stable than the corresponding Hoc-protected derivatives (C) 2010 Elsevier Ltd All rights reserved
• Autotandem Catalysis with Ruthenium: Remote Hydroesterification of Allylic Amides
  作者：Nicolas Armanino、Marc Lafrance、Erick M. Carreira

  DOI：10.1021/ol4034463

  日期：2014.1.17

  A one-pot tandem sequence involving olefin isomerization and hydroesterification has been developed that enables the incorporation of a C-1-unit at the remote terminal position of allylic amides. Key observations suggest that generation of an active ruthenium hydride, formed by addition of acetic acid, allows both processes to take place under mild conditions in an autotandem catalytic, cascading fashion, which is characterized by the use of a single catalytic entity capable of promoting multiple distinct steps without operator intervention.