2-{3-[3-(dioxoisoindolin-2-thio)-2-hydroxy-6-methoxyphenyl]-2-hydroxy-6-methoxyphenylthio}-isoindoline-1,3-dione | 317802-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{3-[3-(dioxoisoindolin-2-thio)-2-hydroxy-6-methoxyphenyl]-2-hydroxy-6-methoxyphenylthio}-isoindoline-1,3-dione
• 英文别名: 2-[3-[3-(1,3-Dioxoisoindol-2-yl)sulfanyl-2-hydroxy-6-methoxyphenyl]-2-hydroxy-4-methoxyphenyl]sulfanylisoindole-1,3-dione
• CAS: 317802-81-6；419560-49-9；234766-03-1
• 化学式: C₃₀H₂₀N₂O₈S₂
• 分子量: 600.629
• InChiKey: MJLBISQBIUECMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-{3-[3-(dioxoisoindolin-2-thio)-2-hydroxy-6-methoxyphenyl]-2-hydroxy-6-methoxyphenylthio}-isoindoline-1,3-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 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
• 作为产物：
  描述：

  phthalimidesulfenyl chloride 、 (M)-6,6'-dimethoxy-2,2'-biphenol 以 氯仿 为溶剂， 反应 3.0h， 以82%的产率得到2-{3-[3-(dioxoisoindolin-2-thio)-2-hydroxy-6-methoxyphenyl]-2-hydroxy-6-methoxyphenylthio}-isoindoline-1,3-dione
  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

• A Base-Mediated Mild Sulfenylation of Indoles and Pyrrole with α-Acylthiones
  作者：Caterina Viglianisi、Enrico Marcantoni、Vanessa Carapacchi、Stefano Menichetti、Laura Marsili

  DOI：10.1002/ejoc.201402894

  日期：2014.10

  procedure for the sulfenylation of indoles and pyrroles based on an aromatic substitution with α-acylthiones used as electrophiles is described. The sulfenylating species were obtained, under very mild reaction conditions, from N-thiophthalimides, using a weak base (pyridine or triethylamine) as promoter. The overall yields obtained are comparable with those obtained by other known sulfenylation protocols

  描述了一种基于芳香取代的吲哚和吡咯磺基化的新程序，其中 α-酰基硫酮用作亲电子试剂。使用弱碱（吡啶或三乙胺）作为促进剂，在非常温和的反应条件下，从 N-硫代邻苯二甲酰亚胺获得亚磺酰化物质。获得的总产率与通过其他已知的亚磺酰化方案获得的产率相当，后者通常需要更苛刻的反应条件和/或含金属的路易斯酸作为促进剂。
• Electrophilic Substitution of Phenols with α,α′-Dioxothiones andortho-Thioquinones
  作者：Giuseppe Capozzi、Stefano Menichetti、Cristina Nativi

  DOI：10.1002/1099-0690(200011)2000:21<3653::aid-ejoc3653>3.0.co;2-0

  日期：2000.11

  α,α′-Dioxothione 1a and ortho-thioquinones 2a and 2b are able to react with several phenols and N,N-dimethylaniline to give the corresponding alkyl aryl or diaryl sulfides. The mechanism of this reaction was proved to be an electrophilic aromatic substitution undergone by the highly polarised carbon−sulfur double bond. Following this procedure, the atropoisomeric biphenyl compound 26 was also prepared

  α,α'-二氧硫酮 1a 和邻硫醌 2a 和 2b 能够与几种酚和 N,N-二甲基苯胺反应生成相应的烷基芳基或二芳基硫化物。该反应的机理被证明是由高度极化的碳硫双键进行的亲电芳香取代。在该程序之后，还制备了阻转异构联苯化合物26。
• 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.