(M,M)-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-dodecaene-25,26,27,28-tetraol | 234766-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (M,M)-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-dodecaene-25,26,27,28-tetraol
• 英文别名: 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-dodecaene-25,26,27,28-tetraol；3,12,15,24-Tetramethoxy-7,8,19,20-tetrathiapentacyclo[19.3.1.12,6.19,13.114,18]octacosa-1(24),2,4,6(28),9(27),10,12,14,16,18(26),21(25),22-dodecaene-25,26,27,28-tetrol
• CAS: 234766-05-3
• 化学式: C₂₈H₂₄O₈S₄
• 分子量: 616.758
• InChiKey: SHTIVYHBZQHROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  219
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (M,M)-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-dodecaene-25,26,27,28-tetraol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以61%的产率得到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 5.33h， 生成 (M,M)-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-dodecaene-25,26,27,28-tetraol
  参考文献：
  名称：

  Phthalimidesulfenyl chloride part 13.1 3,3′-regioselective thiofunctionalization of atropisomeric 2,2′-biphenols

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(99)00762-5

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.
• 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.