2-Hydroxy-naphthothio phthalimide | 160855-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Hydroxy-naphthothio phthalimide
• 英文别名: 2-((2-hydroxynaphthalen-1-yl)thio)isoindoline-1,3-dione；2-(2-Hydroxynaphthalen-1-yl)sulfanylisoindole-1,3-dione
• CAS: 160855-18-5
• 化学式: C₁₈H₁₁NO₃S
• 分子量: 321.356
• InChiKey: IPCKDFUJLQKSOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-naphthothio phthalimide 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 240.75h， 生成 methyl (4S,5R)-2,6-di-O-benzyl-4-thio-α-L-threo-hexopyranosid[4,5-b]naphtho[1,2-e]-S-oxo-1,4-oxathiin
  参考文献：
  名称：

  Conformational evaluation of some 4-deoxyhex-4-enopyranose derivatives and their use in the preparation of a previously undescribed class of 3-thio-l-sorbopyranosides and their 6-C-methoxy analogues

  摘要：

  A new series of thio-substituted sugars were synthesised relying on the totally regio- and stereoselective cycloaddition of 4-deoxyhex-4-enopyranose derivatives to 'in situ' generated oxothiones. Conformational studies of the above unsaturated sugars showed a marked prevalence of the all-axial conformer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00431-7
• 作为产物：
  描述：

  phthalimidesulfenyl chloride 、 2-萘酚 以 氯仿 为溶剂， 反应 2.0h， 以98%的产率得到2-Hydroxy-naphthothio phthalimide
  参考文献：
  名称：

  Phthalimidesulfenyl chloride part 8. Reaction with activated arenes: the first example of ortho-thioquinones generation

  摘要：

  Phthalimidesulfenyl chloride 1 reacts with activated arenes 2a-g, to give monosubstituted derivatives 3a-g. Hydroxysulfenyl compounds 3a-d have been used as suitable source of alpha-oxothiones (ortho-thioquinones) 4a-d, which act as heterodienes in 4+2 cycloaddition reactions.

  DOI：

  10.1016/s0040-4039(00)78568-6

文献信息

• A Straightforward Route to Potent Phenolic Chain‐Breaking Antioxidants by Acid‐Promoted Transposition of 1,4‐Benzo[ <i>b</i> ]oxathiines to Dihydrobenzo[ <i>b</i> ]thiophenes
  作者：Caterina Viglianisi、Riccardo Amorati、Leonardo Di Pietro、Stefano Menichetti

  DOI：10.1002/chem.201502650

  日期：2015.11.9

  The transformation of simple phenols with limited antioxidant activity into potent chain‐breaking antioxidants was achieved by a three‐step protocol, consisting of the conversion of phenols into 1,4‐benzo[b]oxathiines followed by an unprecedented acid‐promoted transposition to o‐hydroxydihydrobenzo[b]thiophenes, or dihydrobenzo[de]thiochromenes, starting from phenols or naphthols, respectively. These

  将抗氧化剂活性有限的简单酚类转化为有效的链断裂抗氧化剂，可通过三步操作完成，包括将酚类转化为1,4-苯并[ b ]恶二环烷，然后再进行前所未有的酸促成转位为邻位。 -羟基二氢苯并[ b ]噻吩或二氢苯并[ de ]噻吩，分别从酚或萘酚开始。这些衍生物，轴承与硫醚硫苯并稠合的杂环邻位的酚OH，具有反应与烷基过氧自由基的速率常数（ķ INH）与α-生育酚相当 提出了关于转座机理以及结构与抗氧化剂活性关系的坚实原理。
• α-oxosulfines part 2: The first example of Ortho-thioquinone-S-oxides
  作者：Giuseppe Capozzi、Paola Fratini、Stefano Menichetti、Cristina Nativi

  DOI：10.1016/0040-4020(96)00711-9

  日期：1996.9

  Benzo-oxathiin-S-oxides 9b and 9c can undergo a Retro Diels-Alder (RDA) reaction to from ortho-thioquinone-S-oxides 12 and 11. These hitherto unknown reactive intermediates can be successfully generated as function of the geometry of the starting sulfoxides and the type of aromatic system involved, and can be trapped as electron poor dienes or dienophiles.

  苯并草硫素-S-氧化物9b和9c可以经历Retro Diels-Alder（RDA）反应，形成邻-硫代醌-S-氧化物12和11。这些迄今未知的反应性中间体可以根据起始亚砜的几何形状和所涉及的芳族体系的类型而成功生成，并可以捕获为电子贫乏的二烯或亲二烯体。
• Hetero Diels–Alder reactions of o-thioquinones with cyclic dienes: an efficient synthesis of novel heterocyclic compounds
  作者：Vijay Nair、Bini Mathew、Nigam P Rath、M Vairamani、S Prabhakar

  DOI：10.1016/s0040-4020(01)00814-6

  日期：2001.9

  o-Thioquinones undergo facile hetero Diels–Alder reactions with cyclic dienes leading to novel heterocyclic compounds.

  邻噻吩醌容易与环二烯发生杂Diels-Alder反应，生成新的杂环化合物。
• [2+4] vs [4+2] Cycloaddition reactions of o-thioquinones with 1,3-dienes
  作者：Stefano Menichetti、Caterina Viglianisi

  DOI：10.1016/s0040-4020(03)00811-1

  日期：2003.7

  Under kinetic control, the reaction of o-thioquinones with acyclic 1,3-dienes afforded, as main products, the spiro cycloadducts deriving from the participation of the thiones as dienophiles. Under thermodynamic control, or with cyclic dienes, the thioquinones behave as hetero dienes to give the benzoxathiin derivatives with complete regioselectivity.

  在动力学控制下，邻硫醌与无环1，3-二烯的反应作为主要产物提供了由硫酮作为亲二烯体的参与而形成的螺环加合物。在热力学控制下，或在环状二烯的作用下，硫醌具有杂二烯的作用，从而使苯并黄嘌呤衍生物具有完全的区域选择性。
• An Efficient Catalytic Method for Regioselective Sulfenylation of Electron-Rich Aza-Aromatics at Room Temperature
  作者：Enrico Marcantoni、Roberto Cipolletti、Laura Marsili、Stefano Menichetti、Roberta Properzi、Caterina Viglianisi

  DOI：10.1002/ejoc.201201100

  日期：2013.1

  regioselective carbon–sulfur-bond-forming electrophilic aromatic substitution reaction. The reaction occurred under mild conditions, and the products were obtained in good to excellent yields. The method represents an efficient preparation of sulfenyl aza-aromatics, which are useful intermediates for important organic transformations, due to the great importance of functionalized indoles among natural compounds

  富含电子的氮杂芳族化合物如吲哚和吡咯是有机化学中特别感兴趣和重要的结构。描述了使用 S-烷基-和 S-芳基硫代邻苯二甲酰亚胺作为亚磺酰化剂将亚磺基区域选择性引入富电子氮杂芳烃的有用方法。CeCl3·7H2O/NaI 的催化量对于促进这种区域选择性碳-硫键形成亲电芳香取代反应至关重要。该反应在温和的条件下进行，以良好至极好的收率获得产物。由于功能化吲哚在天然化合物和药物产品中的重要性，该方法代表了硫基氮杂芳烃的有效制备，它们是重要有机转化的有用中间体。