(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-2-((1E,2Z,4Z,6Z)-cyclooctatetraenyl)-1-methyl-propyl ester | 131346-28-6

• 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: (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-2-((1E,2Z,4Z,6Z)-cyclooctatetraenyl)-1-methyl-propyl ester
• CAS: 131346-28-6
• 化学式: C₂₂H₂₃F₃O₃
• 分子量: 392.418
• InChiKey: MQTPWZXXEJNJHO-FHHZTWCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  bromocyclooctatetraene 在 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-2-((1E,2Z,4Z,6Z)-cyclooctatetraenyl)-1-methyl-propyl ester
  参考文献：
  名称：

  Soluble, chiral polyacetylenes: syntheses and investigation of their solution conformation

  摘要：

  Soluble and highly conjugated polyacetylene derivatives bearing chiral appendages have been synthesized and characterized. The backbone pi --> pi* transition of these polymers showed substantial circular dichroism (CD). The magnitude of the CD for the polymers is characteristic of a disymmetric chromophore. Thus, the chiral side groups twist the main chain in predominantly one sense rather than just electronically perturbing that chromophore. The ellipticity observed for the polyacetylenes studied here, having an alpha-branched substituent on only one of every eight backbone atoms, is of the order of magnitude observed for previously studied chiral polyacetylenes that had alpha-branched substituents on every other backbone atom. This observation suggests that the chirality imparted to the backbone by the substituent is not greatly influenced by the proximity of neighboring substituents. Decreasing temperature had much more influence on the CD of the cis polymers than on the CD of the trans polymers in their respective pi --> pi* regions. cis-Poly-RCOTs (where RCOT is substituted cyclooctatetraene) are much more conformationally flexible and may be helical, although the CD data do not provide conclusive evidence of this conformation.

  DOI：

  10.1021/ja00005a039