(2,2,2-Trifluoro-1-formyl-1-p-tolylsulfanyl-ethyl)-carbamic acid benzyl ester

• 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: (2,2,2-Trifluoro-1-formyl-1-p-tolylsulfanyl-ethyl)-carbamic acid benzyl ester
• 英文别名: Benzyl 2,2,2-trifluoro-1-formyl-1-((4-methylphenyl)thio)ethylcarbamate；benzyl N-[1,1,1-trifluoro-2-(4-methylphenyl)sulfanyl-3-oxopropan-2-yl]carbamate
• 化学式: C₁₈H₁₆F₃NO₃S
• 分子量: 383.391
• InChiKey: AQESYUSLGHYKHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氯丙烯镁 、 (2,2,2-Trifluoro-1-formyl-1-p-tolylsulfanyl-ethyl)-carbamic acid benzyl ester 以 四氢呋喃 为溶剂， 反应 0.02h， 生成 ((1R,2R)-2-Hydroxy-1-p-tolylsulfanyl-1-trifluoromethyl-pent-4-enyl)-carbamic acid benzyl ester 、 ((1R,2S)-2-Hydroxy-1-p-tolylsulfanyl-1-trifluoromethyl-pent-4-enyl)-carbamic acid benzyl ester 、 ((1S,2R)-2-Hydroxy-1-p-tolylsulfanyl-1-trifluoromethyl-pent-4-enyl)-carbamic acid benzyl ester 、 ((1S,2S)-2-Hydroxy-1-p-tolylsulfanyl-1-trifluoromethyl-pent-4-enyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Unusual nonchelation controlled allylation of a N -monoprotected α-amino aldehyde: stereoselective entry to nonracemic trifluoromethyl dipeptide isosteres

  摘要：

  An efficient synthesis of the non-racemic (66-68% e.e.) homoallylic beta -trifluoromethyl beta -amino alcohol (2S,3R)-9, a key intermediate in the synthesis of trifluoromethylated dipeptide isosteres and oligopeptides, was developed starting from N-Cbz-trifluoropyruvaldehyde-N,S-ketal (R)-1a. The correct syn-stereochemistry was achieved by combining two moderately stereoselective steps: (1) addition of allylmagnesium chloride to (R)-1a, occurring with unusual nonchelation control; (2) reductive: desulfenylation of the phenylacetate 6 with NaBH4/pyridine. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00363-3