tert-butyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate | 879220-81-2

• 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: tert-butyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate
• 英文别名: tert-butyl (E,5S)-4,4-difluoro-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-2-enoate
• CAS: 879220-81-2
• 化学式: C₂₁H₂₉F₂NO₄
• 分子量: 397.462
• InChiKey: GVQDHCSMJQYRHR-DBTPVHCXSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  500.2±50.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  tert-butyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate 在 copper(l) iodide 、 甲基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以85.9%的产率得到tert-butyl (5S,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-6-phenylhex-3-enoate
  参考文献：
  名称：

  Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosteres To Probe Structural Requirements of the Peptide Transporter PEPT1

  摘要：

  Described is a novel synthetic route for dipeptide isosteres containing (Z)-alkene and (E)-fluoroalkene units as cis-amide bond equivalents via organocopper-mediated reduction of gamma-acetoxy- or gamma,gamma-difluoro-alpha,beta-unsaturated-delta-lactams. The synthesized isosteres were evaluated in terms of their affinities for the peptide transporter PEPT1. traps-Amide isosteres tended to possess higher affinities for PEPT1 as compared to the corresponding cis-amide bond equivalents.

  DOI：

  10.1021/ol052781k
• 作为产物：
  描述：

  ethyl (3S)-3-[N-(tert-butoxycarbonyl)amino]-2,2-difluoro-4-phenylbutanoate 在 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 tert-butyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate
  参考文献：
  名称：

  Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosteres To Probe Structural Requirements of the Peptide Transporter PEPT1

  摘要：

  Described is a novel synthetic route for dipeptide isosteres containing (Z)-alkene and (E)-fluoroalkene units as cis-amide bond equivalents via organocopper-mediated reduction of gamma-acetoxy- or gamma,gamma-difluoro-alpha,beta-unsaturated-delta-lactams. The synthesized isosteres were evaluated in terms of their affinities for the peptide transporter PEPT1. traps-Amide isosteres tended to possess higher affinities for PEPT1 as compared to the corresponding cis-amide bond equivalents.

  DOI：

  10.1021/ol052781k

文献信息

• Facile Synthesis of Fluoroalkenes by Palladium-Catalyzed Reductive Defluorination of Allylic <i>gem</i>-Difluorides
  作者：Tetsuo Narumi、Kenji Tomita、Eriko Inokuchi、Kazuya Kobayashi、Shinya Oishi、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1021/ol701627v

  日期：2007.8.1

  stereoselective synthesis of fluoroalkenes was achieved in excellent yields via Pd-catalyzed C-F bond activation. In this transformation, Et3N plays a crucial role to produce reactive hydride species such as Ph(EtO)SiH2 and Ph(EtO)2SiH by promoting dehydrogenative coupling. The reaction proceeds efficiently at 50 degrees C with a variety of substrates and is also useful for the synthesis of fluoroalkene

  通过钯催化的CF键活化，以优异的产率实现了氟烯烃的化学和立体选择性合成。在此转化过程中，Et3N在促进反应性氢化物物种（如Ph（EtO）SiH2和Ph（EtO）2SiH）中起关键作用，它可以促进脱氢偶联。该反应可在50摄氏度下与多种底物高效进行，也可用于合成氟代烯烃拟肽。