(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)butylcarbamate | 888725-65-3

• 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: (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)butylcarbamate
• 英文别名: benzyl N-[(1S,2R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(trifluoromethyl)butyl]carbamate
• CAS: 888725-65-3
• 化学式: C₁₈H₂₄F₃NO₄
• 分子量: 375.388
• InChiKey: MEGNCEOERYMQGF-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)butylcarbamate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以93%的产率得到benzyl (2R,3S,4R)-1,2-dihydroxy-4-(trifluoromethyl)hexan-3-ylcarbamate
  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
• 作为产物：
  描述：

  L-甘油醛缩丙酮 在 palladium on activated charcoal indium 、 氢气 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)butylcarbamate
  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