4-difluoromethyl-5,5-difluoro-2-oxo-pent-3-enoic acid ethyl ester | 1002331-13-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-difluoromethyl-5,5-difluoro-2-oxo-pent-3-enoic acid ethyl ester
• 英文别名: Ethyl 4-(difluoromethyl)-5,5-difluoro-2-oxopent-3-enoate；ethyl 4-(difluoromethyl)-5,5-difluoro-2-oxopent-3-enoate
• CAS: 1002331-13-6
• 化学式: C₈H₈F₄O₃
• 分子量: 228.143
• InChiKey: CPTNBLWAEPVGNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-difluoromethyl-5,5-difluoro-2-oxo-pent-3-enoic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.67h， 生成 4-difluoromethyl-5,5-difluoro-2-oxo-pentanoic acid ethyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine

  摘要：

  We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.

  DOI：

  10.1021/ol702470j
• 作为产物：
  描述：

  1,1,3,3-四氟-2-丙酮 、 (三苯基膦)丙酮酸乙酯 以 苯 为溶剂， 以71%的产率得到4-difluoromethyl-5,5-difluoro-2-oxo-pent-3-enoic acid ethyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine

  摘要：

  We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.

  DOI：

  10.1021/ol702470j

文献信息

• Chemoenzymatic Synthesis of (<i>S</i>)-Hexafluoroleucine and (<i>S</i>)-Tetrafluoroleucine
  作者：Hsien-Po Chiu、Richard P. Cheng

  DOI：10.1021/ol702470j

  日期：2007.12.1

  We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.