N-(2-hydroxy-5-methoxyphenylthio)phthalimide | 178161-08-5

• 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: N-(2-hydroxy-5-methoxyphenylthio)phthalimide
• 英文别名: 2-[(2-Hydroxy-5-methoxyphenyl)thio]-1H-isoindole-1,3(2H)-dione；2-(2-hydroxy-5-methoxyphenyl)sulfanylisoindole-1,3-dione
• CAS: 178161-08-5
• 化学式: C₁₅H₁₁NO₄S
• 分子量: 301.323
• InChiKey: CVDPVLLANWGZNG-UHFFFAOYSA-N

物化性质

• 沸点：
  507.3±60.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-5-methoxyphenylthio)phthalimide 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 4-(6-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)phenol
  参考文献：
  名称：

  Thiaflavan scavenges radicals and inhibits DNA oxidation: A story from the ferrocene modification

  摘要：

  4-Thiaflavan is a sulfur-substituted flavonoid with a benzoxathiin scaffold. The aim of this work is to compare abilities of sulfur and oxygen atom, hydroxyl groups, and ferrocene moiety at different positions of 4-thiaflavan to trap radicals and to inhibit DNA oxidation. It is found that abilities of thiaflavans to trap radicals and to inhibit DNA oxidation are increased in the presence of ferrocene moiety and are further improved by the electron-donating group attaching to thiaflavan skeleton. It can be concluded that the ferrocene moiety plays the major role for thiaflavans to be antioxidants even in the absence of phenolic hydroxyl groups. On the other hand, the antioxidant effectiveness of phenolic hydroxyl groups in thiaflavans can be improved by the electron-donating group. The influences of sulfur and oxygen atoms in thiaflavans on the antioxidant property of para-hydroxyl group exhibit different manners when the thiaflavans are used to trap radicals and to inhibit DNA oxidation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.081
• 作为产物：
  描述：

  phthalimidesulfenyl chloride 、 4-甲氧基苯酚 以 氯仿 为溶剂， 反应 16.0h， 生成 N-(2-hydroxy-5-methoxyphenylthio)phthalimide
  参考文献：
  名称：

  Thiaflavan scavenges radicals and inhibits DNA oxidation: A story from the ferrocene modification

  摘要：

  4-Thiaflavan is a sulfur-substituted flavonoid with a benzoxathiin scaffold. The aim of this work is to compare abilities of sulfur and oxygen atom, hydroxyl groups, and ferrocene moiety at different positions of 4-thiaflavan to trap radicals and to inhibit DNA oxidation. It is found that abilities of thiaflavans to trap radicals and to inhibit DNA oxidation are increased in the presence of ferrocene moiety and are further improved by the electron-donating group attaching to thiaflavan skeleton. It can be concluded that the ferrocene moiety plays the major role for thiaflavans to be antioxidants even in the absence of phenolic hydroxyl groups. On the other hand, the antioxidant effectiveness of phenolic hydroxyl groups in thiaflavans can be improved by the electron-donating group. The influences of sulfur and oxygen atoms in thiaflavans on the antioxidant property of para-hydroxyl group exhibit different manners when the thiaflavans are used to trap radicals and to inhibit DNA oxidation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.081

文献信息

• Novel cycloadditions of ortho-thioquinones with acyclic dienes: expeditious synthesis of 1,4-benzooxathiines
  作者：Vijay Nair、Bini Mathew、Siji Thomas、Mariappanadar Vairamani、Sripadi Prabhakar

  DOI：10.1039/b106265b

  日期：2001.11.15

  ortho-Thioquinones generated in situ from N-(o-hydroxyphenylsulfanyl)phthalimides easily undergo [4 + 2] cycloaddition reaction with acyclic dienes to afford novel heterocyclic compounds.

  邻硫酮类化合物由N-(邻羟基苯硫基)酞酰亚胺现场生成，能轻易与非环二烯发生[4 + 2]环加成反应，得到新型杂环化合物。
• 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。
• 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。
• [4 + 1] Cycloaddition Reactions of<i>o</i>-Thioquinones with Isocyanides: Novel Syntheses of 2-Imino-1,3-Oxathioles
  作者：Vijay Nair、Bini Mathew、A. U. Vinod、Joseph Swaroop Mathen、Sindu Ros、Rajeev S. Menon、R. Luxmi Varma、R. Srinivas

  DOI：10.1055/s-2003-38072

  日期：——

  o-Thioquinones, generated in situ from o-hydroxyphenylthiophthalimides, underwent facile [4 + 1] cycloaddition reactions with isocyanides to afford 2-imino-1,3-oxathioles.

  由邻羟基苯基硫代邻苯二甲酰亚胺原位生成的邻硫醌与异氰化物进行简单的 [4 + 1] 环加成反应，得到 2-亚氨基-1,3-氧代硫醇。
• Phthalimidesulfenyl Chloride.¹ 11. Generation, General Reactivity, and Synthetic Applications of <i>o</i>-Thioquinones
  作者：G. Capozzi、C. Falciani、S. Menichetti、C. Nativi

  DOI：10.1021/jo962014m

  日期：1997.4.1