S-trifluoroacetamide | 1217352-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: S-trifluoroacetamide
• 英文别名: (2S)-2-phenyl-1-(trifluoroacetyl)piperidine；2,2,2-trifluoro-1-[(2S)-2-phenylpiperidin-1-yl]ethanone
• CAS: 1217352-79-8
• 化学式: C₁₃H₁₄F₃NO
• 分子量: 257.255
• InChiKey: NOPYITFBECPYMC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-trifluoroacetamide 在 sodium periodate 、 rhodium(III) chloride hydrate 、 水 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 90.0h， 生成 N-trifluoroacetylpipecolic acid
  参考文献：
  名称：

  Stereoselective Syntheses of l-Pipecolic Acid and (2S,3S)-3-Hydroxypipecolic Acid from a Chiral N-Imino-2-phenyl-1,2-dihydropyridine Intermediate

  摘要：

  Stereoselective syntheses of L-pipecolic acid and (2S,3S)3-hydroxypipecolic acid were achieved from a chiral N-imino-2-phenyl-1,2-dlhydropyridine intermediate. The 3-hydroxy substituent of the latter amino acid was introduced by hetero-Diels-Alder reaction of singlet oxygen with the 1,2-dihydropyridine.

  DOI：

  10.1021/jo902527s
• 作为产物：
  描述：

  苯基溴化镁 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， -78.0~50.0 ℃ 、5.07 MPa 条件下， 反应 30.0h， 生成 R-trifluoroacetamide 、 S-trifluoroacetamide
  参考文献：
  名称：

  通过分子内还原胺化进行2-取代吡咯烷的对映选择性合成

  摘要：

  作为有机合成中的特殊主题胺化反应的一部分发布 抽象的 通过由铱和手性二茂铁配体原位生成的配合物催化，叔丁基（4-氧代-4-芳基丁基）氨基甲酸酯底物被脱保护，然后被还原环化，以一锅方式形成2-取代的芳基吡咯烷。分子内还原胺化是关键步骤。合成了一系列手性2-取代的芳基吡咯烷，产率高达98％，ee高达92％。 通过由铱和手性二茂铁配体原位生成的配合物催化，叔丁基（4-氧代-4-芳基丁基）氨基甲酸酯底物被脱保护，然后被还原环化，以一锅方式形成2-取代的芳基吡咯烷。分子内还原胺化是关键步骤。合成了一系列手性2-取代的芳基吡咯烷，产率高达98％，ee高达92％。

  DOI：

  10.1055/s-0037-1611533

文献信息

• Chiral Lewis base promoted trichlorosilane reduction of ketimines. An enantioselective organocatalytic synthesis of chiral amines
  作者：Stefania Guizzetti、Maurizio Benaglia、Franco Cozzi、Rita Annunziata

  DOI：10.1016/j.tet.2009.06.015

  日期：2009.8

  The reduction of the carbon-nitrogen double bond is an important transformation. Here we report our studies on a family of chiral organic catalysts able to promote the stereoselective reduction of ketimines with trichlorosilane. The very cheap, metal-free catalysts were easily prepared in one step from commercially available products, namely a chiral aminoalcohol and picolinic acid derivatives. The catalyst structure was extensively modified in a study that allowed to identify an extremely active species, able to promote the reduction on a large variety of substrates with high efficiency (up to 95% ee). A three component methodology has been also developed, where the enantiomerically enriched amine was isolated after performing the reaction by mixing a ketone and an amine in the presence of trichlorosilane and the catalyst. Its synthetic potentiality was demonstrated by employing the present metal-free catalytic procedure in the preparation of (S)-metolachlor, a potent and widely used herbicide. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of 2-Substituted Pyrrolidines via Intramolecular­ Reductive Amination
  作者：Huan Zhou、Wenlei Zhao、Tao Zhang、Haodong Guo、Haizhou Huang、Mingxin Chang

  DOI：10.1055/s-0037-1611533

  日期：2019.7

  Reactions in Organic Synthesis Abstract Catalyzed by the complex generated in situ from iridium and the chiral ferrocene ligand, tert-butyl (4-oxo-4-arylbutyl)carbamate substrates were deprotected and then reductively cyclised to form 2-substituted arylpyrrolidines in a one-pot manner, in which the intramolecular reductive amination was the key step. A range of chiral 2-substituted arylpyrrolidines were

  作为有机合成中的特殊主题胺化反应的一部分发布 抽象的 通过由铱和手性二茂铁配体原位生成的配合物催化，叔丁基（4-氧代-4-芳基丁基）氨基甲酸酯底物被脱保护，然后被还原环化，以一锅方式形成2-取代的芳基吡咯烷。分子内还原胺化是关键步骤。合成了一系列手性2-取代的芳基吡咯烷，产率高达98％，ee高达92％。 通过由铱和手性二茂铁配体原位生成的配合物催化，叔丁基（4-氧代-4-芳基丁基）氨基甲酸酯底物被脱保护，然后被还原环化，以一锅方式形成2-取代的芳基吡咯烷。分子内还原胺化是关键步骤。合成了一系列手性2-取代的芳基吡咯烷，产率高达98％，ee高达92％。
• Stereoselective Syntheses of <scp>l</scp>-Pipecolic Acid and (2<i>S</i>,3<i>S</i>)-3-Hydroxypipecolic Acid from a Chiral <i>N</i>-Imino-2-phenyl-1,2-dihydropyridine Intermediate
  作者：Alexandre Lemire、André B. Charette

  DOI：10.1021/jo902527s

  日期：2010.3.19

  Stereoselective syntheses of L-pipecolic acid and (2S,3S)3-hydroxypipecolic acid were achieved from a chiral N-imino-2-phenyl-1,2-dlhydropyridine intermediate. The 3-hydroxy substituent of the latter amino acid was introduced by hetero-Diels-Alder reaction of singlet oxygen with the 1,2-dihydropyridine.