6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl | 13341-01-0

• 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: 6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl
• 英文别名: 2,2',6,6'-Tetramethoxy-3,3'-dimethyl-biphenyl；2-(2,6-Dimethoxy-3-methylphenyl)-1,3-dimethoxy-4-methylbenzene
• CAS: 13341-01-0
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: NRUUYHCEGKLARA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以88%的产率得到6,6'-dimethoxy-3,3'-dimethyl-2,2'-dhydroxy-1,1'-biphenyl
  参考文献：
  名称：

  Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6,6′,2,2′-tetramethoxy-1,1′-biphenyl

  摘要：

  Regioselective bromination of the title biphenyl 1 at the 3 and 3' positions and simultaneous desymmetrization of the biphenyl has been achieved. Metal-halide exchange at the 3,3' positions facilitated the introduction of functional groups in good yield. Regioselective reduction was obtained by using (CH3)(3)SiI, L-Selectride and HI according to the functional groups on the biphenyls. Resolution of 6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl 3 was achieved by its conversion to the corresponding phosphorothioamidate diastereomers of the (S)-(-)-alpha -methylbenzylamine. The absolute configuration of (M)-(+)-3 was confirmed by X-ray analysis of the corresponding diastereomer. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00410-9
• 作为产物：
  描述：

  碘甲烷 、 1-Bromo-3-(3-bromo-2,6-dimethoxyphenyl)-2,4-dimethoxybenzene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 苯 为溶剂， 反应 24.0h， 以60%的产率得到6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl
  参考文献：
  名称：

  Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6,6′,2,2′-tetramethoxy-1,1′-biphenyl

  摘要：

  Regioselective bromination of the title biphenyl 1 at the 3 and 3' positions and simultaneous desymmetrization of the biphenyl has been achieved. Metal-halide exchange at the 3,3' positions facilitated the introduction of functional groups in good yield. Regioselective reduction was obtained by using (CH3)(3)SiI, L-Selectride and HI according to the functional groups on the biphenyls. Resolution of 6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl 3 was achieved by its conversion to the corresponding phosphorothioamidate diastereomers of the (S)-(-)-alpha -methylbenzylamine. The absolute configuration of (M)-(+)-3 was confirmed by X-ray analysis of the corresponding diastereomer. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00410-9

文献信息

• Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6,6′,2,2′-tetramethoxy-1,1′-biphenyl
  作者：Giovanna Delogu、Davide Fabbri、Maria Antonietta Dettori、Alessandra Forni、Gianluigi Casalone

  DOI：10.1016/s0957-4166(00)00410-9

  日期：2000.11

  Regioselective bromination of the title biphenyl 1 at the 3 and 3' positions and simultaneous desymmetrization of the biphenyl has been achieved. Metal-halide exchange at the 3,3' positions facilitated the introduction of functional groups in good yield. Regioselective reduction was obtained by using (CH3)(3)SiI, L-Selectride and HI according to the functional groups on the biphenyls. Resolution of 6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl 3 was achieved by its conversion to the corresponding phosphorothioamidate diastereomers of the (S)-(-)-alpha -methylbenzylamine. The absolute configuration of (M)-(+)-3 was confirmed by X-ray analysis of the corresponding diastereomer. (C) 2000 Elsevier Science Ltd. All rights reserved.