(Ra)-2,2',6,6'-tetramethoxy-3,3'-dimethylmercapto-1,1'-biphenyl | 328587-55-9

• 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: (Ra)-2,2',6,6'-tetramethoxy-3,3'-dimethylmercapto-1,1'-biphenyl
• 英文别名: (Sa)-2,2',6,6'-tetramethoxy-3,3'-dimethylmercapto-1,1'-biphenyl；2,2',6,6'-tetramethoxy-3,3'-dimethylmercapto-1,1'-biphenyl；2-(2,6-Dimethoxy-3-methylsulfanylphenyl)-1,3-dimethoxy-4-methylsulfanylbenzene；2-(2,6-dimethoxy-3-methylsulfanylphenyl)-1,3-dimethoxy-4-methylsulfanylbenzene
• CAS: 328587-55-9；443282-84-6；443282-85-7
• 化学式: C₁₈H₂₂O₄S₂
• 分子量: 366.502
• InChiKey: LFHRKGHIBFYMIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Ra)-2,2',6,6'-tetramethoxy-3,3'-dimethylmercapto-1,1'-biphenyl 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以78%的产率得到2-(2-hydroxy-6-methoxy-3-methylthiophenyl)-3-methoxy-6-methylthiophenol
  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：

  2,2',6,6'-tetramethoxybiphenyl 在 正丁基锂 、 benzyltriethylammonium perbromide 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 36.0h， 生成 (Ra)-2,2',6,6'-tetramethoxy-3,3'-dimethylmercapto-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

• Desymmetrization of 2,2′,6,6′-tetramethoxybiphenyl by regioselective sulfenylation reaction
  作者：Giovanna Delogu、Davide Fabbri、Maria Antonietta Dettori、Giuseppe Capozzi、Stefano Menichetti、Cristina Nativi

  DOI：10.1016/s0957-4166(02)00012-5

  日期：2001.12

  A practical regioselective sulfenylation reaction of the achiral title compound 1 provides desymmetrization and access to C-symmetric sulphur derivatives. Resolution of 2,2",6,6'-tetramethoxy-3,3'-dimercapto-1,1'-biphenyl 7 was achieved by conversion to the corresponding dithiocarbonate diastereomers. The absolute configuration of (aR)-(-)-7 and (aS)-(+)-7 was assigned unambiguously. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.