(E)-N-benzyl-4,4,4-trifluoro-N-((E)-4,4,4-trifluorobut-2-enyl)but-2-en-1-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-benzyl-4,4,4-trifluoro-N-((E)-4,4,4-trifluorobut-2-enyl)but-2-en-1-amine
• 英文别名: (E)-N-benzyl-4,4,4-trifluoro-N-[(E)-4,4,4-trifluorobut-2-enyl]but-2-en-1-amine
• 化学式: C₁₅H₁₅F₆N
• 分子量: 323.281
• InChiKey: BECMMPXGBJDICA-KBXRYBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 indium 、 magnesium sulfate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (E)-N-benzyl-4,4,4-trifluoro-N-((E)-4,4,4-trifluorobut-2-enyl)but-2-en-1-amine
  参考文献：
  名称：

  Indium-Mediated Diastereoselective Allylation of d- and l-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene:  Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines and 4,4,4-Trifluorovaline

  摘要：

  A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro-2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (> 95% de) with moderate yield. The Cbz-protected (2R,3S)-4,4,4-trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.

  DOI：

  10.1021/jo0601157

文献信息

• Indium-Mediated Diastereoselective Allylation of <scp>d</scp>- and <scp>l</scp>-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene:  Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines and 4,4,4-Trifluorovaline
  作者：Qi Chen、Xiao-Long Qiu、Feng-Ling Qing

  DOI：10.1021/jo0601157

  日期：2006.5.1

  A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro-2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (> 95% de) with moderate yield. The Cbz-protected (2R,3S)-4,4,4-trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.