Phenyl-acetic acid (R)-1-(1-benzyloxycarbonylamino-2,2,2-trifluoro-ethyl)-but-3-enyl ester | 352674-37-4

• 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: Phenyl-acetic acid (R)-1-(1-benzyloxycarbonylamino-2,2,2-trifluoro-ethyl)-but-3-enyl ester
• CAS: 352674-37-4
• 化学式: C₂₂H₂₂F₃NO₄
• 分子量: 421.416
• InChiKey: LUHBEAWLCZHQJZ-QSVWIEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Phenyl-acetic acid (R)-1-(1-benzyloxycarbonylamino-2,2,2-trifluoro-ethyl)-but-3-enyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以98%的产率得到((1S,2R)-2-Hydroxy-1-trifluoromethyl-pent-4-enyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Stereocontrolled approaches to (+)- and (−)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere

  摘要：

  Two efficient approaches to both enantiomers of syn-gamma-triffuoromethyl gamma-amino beta-hydroxy butyric acid (gamma-Tfm-GABOB) (10), a new hydroxymethylene (statine) dipeptide isostere, are described. One exploits the recently disclosed 'non-oxidative' Pummerer reaction, by means of which ex-lithium alkyl sulfoxides are used as chiral alpha-hydroxyalkyl anion equivalents in the synthesis of beta-amino alcohols. Trifluoropyruvaldehyde-N,S-ketal (R)-11, a novel stereochemically stable synthetic equivalent of alpha-amino trifluoropropanal, is used in the second approach. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00397-8
• 作为产物：
  描述：

  在 吡啶 、 sodium tetrahydroborate 作用下， 以98%的产率得到Phenyl-acetic acid (R)-1-(1-benzyloxycarbonylamino-2,2,2-trifluoro-ethyl)-but-3-enyl ester
  参考文献：
  名称：

  Stereocontrolled approaches to (+)- and (−)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere

  摘要：

  Two efficient approaches to both enantiomers of syn-gamma-triffuoromethyl gamma-amino beta-hydroxy butyric acid (gamma-Tfm-GABOB) (10), a new hydroxymethylene (statine) dipeptide isostere, are described. One exploits the recently disclosed 'non-oxidative' Pummerer reaction, by means of which ex-lithium alkyl sulfoxides are used as chiral alpha-hydroxyalkyl anion equivalents in the synthesis of beta-amino alcohols. Trifluoropyruvaldehyde-N,S-ketal (R)-11, a novel stereochemically stable synthetic equivalent of alpha-amino trifluoropropanal, is used in the second approach. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00397-8