5,5,5',5'-tetramethoxyl-6,6'-di(4-fluorophenyl)-1,1'-bi(cyclohex-3-ene)-2,2'-dione | 1260433-77-9

• 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: 5,5,5',5'-tetramethoxyl-6,6'-di(4-fluorophenyl)-1,1'-bi(cyclohex-3-ene)-2,2'-dione
• 英文别名: (5R,6S)-5-(4-fluorophenyl)-6-[(1S,6R)-6-(4-fluorophenyl)-5,5-dimethoxy-2-oxocyclohex-3-en-1-yl]-4,4-dimethoxycyclohex-2-en-1-one
• CAS: 1260433-77-9
• 化学式: C₂₈H₂₈F₂O₆
• 分子量: 498.524
• InChiKey: ZLEHMIQPUCHZID-CQJMVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,5,5',5'-tetramethoxyl-6,6'-di(4-fluorophenyl)-1,1'-bi(cyclohex-3-ene)-2,2'-dione 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 以88%的产率得到(S)-5,5'-dimethoxy-6,6'-di(4-fluorophenyl)biphenyl-2,2'-diol
  参考文献：
  名称：

  Enantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange

  摘要：

  A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF3 center dot OEt2. On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.

  DOI：

  10.1021/ja108717r
• 作为产物：
  描述：

  chlorozinc(1+),fluorobenzene 在 三甲基氯硅烷 、 chlorobis(ethylene)rhodium(I) dimer 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 5,5,5',5'-tetramethoxyl-6,6'-di(4-fluorophenyl)-1,1'-bi(cyclohex-3-ene)-2,2'-dione
  参考文献：
  名称：

  Enantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange

  摘要：

  A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF3 center dot OEt2. On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.

  DOI：

  10.1021/ja108717r

文献信息

• Enantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange
  作者：Fenghai Guo、Leah C. Konkol、Regan J. Thomson

  DOI：10.1021/ja108717r

  日期：2011.1.12

  A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF3 center dot OEt2. On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.