(S)-2-[2-diazo-2-(4-trifluoromethylphenyl)acetoxy]propionic acid ethyl ester | 873108-66-8

• 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: (S)-2-[2-diazo-2-(4-trifluoromethylphenyl)acetoxy]propionic acid ethyl ester
• CAS: 873108-66-8
• 化学式: C₁₄H₁₃F₃N₂O₄
• 分子量: 330.263
• InChiKey: WOCZFFVSBIGIAA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[2-diazo-2-(4-trifluoromethylphenyl)acetoxy]propionic acid ethyl ester 、 tert-butyl((4-methoxybenzyl)oxy)dimethylsilane 在 辛酸铑 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 16.75h， 生成 (2R,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-(4-(trifluoromethyl)phenyl)propan-1-ol 、 (2S,3R)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-(4-(trifluoromethyl)phenyl)propan-1-ol 、 3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-(4-(trifluoromethyl)phenyl)propan-1-ol
  参考文献：
  名称：

  Asymmetric Intermolecular C−H Functionalization of Benzyl Silyl Ethers Mediated by Chiral Auxiliary-Based Aryldiazoacetates and Chiral Dirhodium Catalysts

  摘要：

  C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The dirhodium tetraprolinates such as Rh-2((S)-DOSP)(4) have been widely successful as chiral catalysts in the C-H functionalization chemistry of aryldiazoacetates, but give poor enantioselectivity in the reactions of aryldiazoacetates with benzyl silyl ether derivatives. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderately high diastereoselectivity (79-88% de) and enantioselectivity (68-85% ee). The best results (91-95% de, 95-98% ee), however, were achieved using Hashimoto's Rh-2((S)-PTTL)(4) catalyst.

  DOI：

  10.1021/jo051747g
• 作为产物：
  描述：

  L(-)-乳酸乙酯 在 4-二甲氨基吡啶 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 (S)-2-[2-diazo-2-(4-trifluoromethylphenyl)acetoxy]propionic acid ethyl ester
  参考文献：
  名称：

  Asymmetric Intermolecular C−H Functionalization of Benzyl Silyl Ethers Mediated by Chiral Auxiliary-Based Aryldiazoacetates and Chiral Dirhodium Catalysts

  摘要：

  C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The dirhodium tetraprolinates such as Rh-2((S)-DOSP)(4) have been widely successful as chiral catalysts in the C-H functionalization chemistry of aryldiazoacetates, but give poor enantioselectivity in the reactions of aryldiazoacetates with benzyl silyl ether derivatives. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderately high diastereoselectivity (79-88% de) and enantioselectivity (68-85% ee). The best results (91-95% de, 95-98% ee), however, were achieved using Hashimoto's Rh-2((S)-PTTL)(4) catalyst.

  DOI：

  10.1021/jo051747g