(+/-)-cis-ethyl 6,6-difluoro-7-(4-fluoroanilino)-3-cycloheptene-1-carboxylate

• 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: (+/-)-cis-ethyl 6,6-difluoro-7-(4-fluoroanilino)-3-cycloheptene-1-carboxylate
• 英文别名: ethyl (1S,7S)-6,6-difluoro-7-(4-fluoroanilino)cyclohept-3-ene-1-carboxylate
• 化学式: C₁₆H₁₈F₃NO₂
• 分子量: 313.32
• InChiKey: UIKHTGCWWUBCET-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-戊烯酸乙酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium cyanoborohydride 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， -78.0~40.0 ℃ 、199.98 Pa 条件下， 反应 6.0h， 生成 (+/-)-cis-ethyl 6,6-difluoro-7-(4-fluoroanilino)-3-cycloheptene-1-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of Fluorinated, Seven-Membered β-Amino Acid Derivatives via Ring-Closing Metathesis

  摘要：

  [GRAPHICS]Cis and trans seven-membered gamma,gamma-difluorinated beta-amino acid derivatives (III) have been prepared with a sequence that starts with imidoyl halides (I), which are condensed with suitable ester enolates to give intermediates (II). These, in turn, can be cyclized by means of a ringclosing olefin metathesis reaction and the product stereoselectively reduced to yield compounds (III) in good overall yields.

  DOI：

  10.1021/ol034827k

文献信息

• Diastereoselective Synthesis of Fluorinated, Seven-Membered β-Amino Acid Derivatives via Ring-Closing Metathesis
  作者：Santos Fustero、Ana Bartolomé,、Juan F. Sanz-Cervera、María Sánchez-Roselló、Juan García Soler、Carmen Ramírez de Arellano、Antonio Simón Fuentes

  DOI：10.1021/ol034827k

  日期：2003.7.1

  [GRAPHICS]Cis and trans seven-membered gamma,gamma-difluorinated beta-amino acid derivatives (III) have been prepared with a sequence that starts with imidoyl halides (I), which are condensed with suitable ester enolates to give intermediates (II). These, in turn, can be cyclized by means of a ringclosing olefin metathesis reaction and the product stereoselectively reduced to yield compounds (III) in good overall yields.