(S_S,S)-(+)-ethyl N-(tert-butanesulfinyl)-3-amino-4,4,4-trifluoro-3-(2-methoxyphenyl)butanoate | 1417739-69-5

• 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_S,S)-(+)-ethyl N-(tert-butanesulfinyl)-3-amino-4,4,4-trifluoro-3-(2-methoxyphenyl)butanoate
• 英文别名: ethyl (3S)-3-[[(S)-tert-butylsulfinyl]amino]-4,4,4-trifluoro-3-(2-methoxyphenyl)butanoate
• CAS: 1417739-69-5
• 化学式: C₁₇H₂₄F₃NO₄S
• 分子量: 395.443
• InChiKey: LCZFYZBUEROZFH-QMTYFTJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-2-methyl-N-(2,2,2-trifluoro-1-(2-methoxyphenyl)ethylidene)propane-2-sulfinamide 、 溴乙酸乙酯 在 copper(l) chloride 、 锌 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 25.25h， 以14%的产率得到(S_S,S)-(+)-ethyl N-(tert-butanesulfinyl)-3-amino-4,4,4-trifluoro-3-(2-methoxyphenyl)butanoate
  参考文献：
  名称：

  Enantiopure Trifluoromethylated β^3,3-Amino Acids: Synthesis by Asymmetric Reformatsky Reaction with Stable Analogues of Trifluoromethyl N-tert-Butanesulfinylketoimines and Incorporation into α/β-Peptides

  摘要：

  Addition of a Reformatsky reagent to alpha-aryl(alkyl) alpha-trifluoromethyl N-tert-butanesulfinyl hemiaminals, bench-stable surrogates of trifluoromethyl ketoimines, provided beta-alkyl(aryl) beta-trifluoromethyl beta-amino acids derivatives in good yields and high diastereoselectivities. The N-tert-butanesulfinyl beta(3,3)-amino esters were further utilized as versatile intermediates for the elaboration of heterodi- and -tripeptides.

  DOI：

  10.1021/jo302549v

文献信息

• Enantiopure Trifluoromethylated β^3,3-Amino Acids: Synthesis by Asymmetric Reformatsky Reaction with Stable Analogues of Trifluoromethyl <i>N</i>-<i>tert</i>-Butanesulfinylketoimines and Incorporation into α/β-Peptides
  作者：Fabienne Grellepois

  DOI：10.1021/jo302549v

  日期：2013.2.1

  Addition of a Reformatsky reagent to alpha-aryl(alkyl) alpha-trifluoromethyl N-tert-butanesulfinyl hemiaminals, bench-stable surrogates of trifluoromethyl ketoimines, provided beta-alkyl(aryl) beta-trifluoromethyl beta-amino acids derivatives in good yields and high diastereoselectivities. The N-tert-butanesulfinyl beta(3,3)-amino esters were further utilized as versatile intermediates for the elaboration of heterodi- and -tripeptides.