2-(2-hydroxy-6-methoxy-3-sulfanylphenyl)-3-methoxy-6-sulfanylphenol | 419560-54-6

• 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: 2-(2-hydroxy-6-methoxy-3-sulfanylphenyl)-3-methoxy-6-sulfanylphenol
• CAS: 419560-54-6；419560-87-5；234766-04-2
• 化学式: C₁₄H₁₄O₄S₂
• 分子量: 310.395
• InChiKey: BNSLKPARNDMUDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.9
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxy-6-methoxy-3-sulfanylphenyl)-3-methoxy-6-sulfanylphenol 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 25,26,27,28-tetrahydroxy-3,12,15,24-tetramethoxy-7,8,19,20-tetrathiapentacyclo[19.3.1.1<2,6>.1<9,13>.1<14,18>]octacosa-1(25),2,4,6(26),9(27),10,12,14(28),15,17,21,23-dodecaen-7-one
  参考文献：
  名称：

  Regiocontrolled Synthesis of Enantiopure 3,3‘-Thiosubstituted Biphenyls

  摘要：

  Sulfenylation of 6,6'-dimethoxy-2,2'-dihydroxybiphenyl, used as a racemic mixture and single enantiomers, by phthalimidesulfenyl chloride afforded the corresponding 3,3'-N,N'-dithiophthalimide with complete regioselectivity. Simple manipulations of the latter compound allowed access to the corresponding bis-thiol or o-thioquinone as useful intermediates for the synthesis of new sulfur-containing open-chain and macrocyclic C-2 enantiopure ligands. The application of this methodology to the preparation of a biphenyl bearing two cysteine units as potential HIV-1 protease inhibitor is also described.

  DOI：

  10.1021/jo0157627
• 作为产物：
  描述：

  2-(2-羟基-6-甲氧基苯基)-3-甲氧基苯酚 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.0h， 生成 2-(2-hydroxy-6-methoxy-3-sulfanylphenyl)-3-methoxy-6-sulfanylphenol
  参考文献：
  名称：

  Regiocontrolled Synthesis of Enantiopure 3,3‘-Thiosubstituted Biphenyls

  摘要：

  Sulfenylation of 6,6'-dimethoxy-2,2'-dihydroxybiphenyl, used as a racemic mixture and single enantiomers, by phthalimidesulfenyl chloride afforded the corresponding 3,3'-N,N'-dithiophthalimide with complete regioselectivity. Simple manipulations of the latter compound allowed access to the corresponding bis-thiol or o-thioquinone as useful intermediates for the synthesis of new sulfur-containing open-chain and macrocyclic C-2 enantiopure ligands. The application of this methodology to the preparation of a biphenyl bearing two cysteine units as potential HIV-1 protease inhibitor is also described.

  DOI：

  10.1021/jo0157627

文献信息

• Phthalimidesulfenyl chloride part 13.1 3,3′-regioselective thiofunctionalization of atropisomeric 2,2′-biphenols
  作者：Giuseppe Capozzi、Giovanna Delogu、Maria A. Dettori、Davide Fabbri、Stefano Menichetti、Cristina Nativi、Roberta Nuti

  DOI：10.1016/s0040-4039(99)00762-5

  日期：1999.6

  Regioselective 3,3'-thiofunctionalization of atropisomeric biphenol 2 can be achieved using phthalimidesulfenyl chloride as the key reagent. The bis-thiophthalimide derivative 3 is the starting material for the preparation of linear (7a-d) and macrocyclic (15a-d) C-2 symmetric ligands containing the biphenyl moiety. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.
• Regiocontrolled Synthesis of Enantiopure 3,3‘-Thiosubstituted Biphenyls
  作者：Giuseppe Capozzi、Giovanna Delogu、Davide Fabbri、Manuela Marini、Stefano Menichetti、Cristina Nativi

  DOI：10.1021/jo0157627

  日期：2002.4.1

  Sulfenylation of 6,6'-dimethoxy-2,2'-dihydroxybiphenyl, used as a racemic mixture and single enantiomers, by phthalimidesulfenyl chloride afforded the corresponding 3,3'-N,N'-dithiophthalimide with complete regioselectivity. Simple manipulations of the latter compound allowed access to the corresponding bis-thiol or o-thioquinone as useful intermediates for the synthesis of new sulfur-containing open-chain and macrocyclic C-2 enantiopure ligands. The application of this methodology to the preparation of a biphenyl bearing two cysteine units as potential HIV-1 protease inhibitor is also described.