N-(2-hydroxy-4-methoxyphenylthio)phthalimide | 160855-15-2

• 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-4-methoxyphenylthio)phthalimide
• 英文别名: 2-(2-Hydroxy-4-methoxyphenyl)sulfanylisoindole-1,3-dione
• CAS: 160855-15-2
• 化学式: C₁₅H₁₁NO₄S
• 分子量: 301.323
• InChiKey: HMORUQLOWUCBTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  508.6±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-4-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-(7-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：

  3-甲氧基苯酚 、 phthalimidesulfenyl chloride 以 氯仿 为溶剂， 反应 16.0h， 生成 N-(2-hydroxy-4-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

• Helical-Shaped Bis-1,4-benzoxathiines through an Inverse-Electron-Demand Hetero-Diels-Alder Reaction of<i>ortho</i>-Thioquinones
  作者：Caterina Viglianisi、Stefano Menichetti、Sara Piantini、Lorenzo Tofani

  DOI：10.1002/ejoc.201600850

  日期：2016.11

  The reaction of transient ortho-thioquinones, which act as electron-poor dienes, with properly designed bis-dienophiles leads to the formation of helical-shaped bis-benzoxathiine cycloadducts with complete control of the regiochemistry and the relative stereochemistry. Bis-benzoxathiines were the result of two consecutive inverse-electron-demand cycloaddition processes with stereospecific approach

  充当缺电子二烯的瞬态邻硫醌与适当设计的双亲二烯体的反应导致形成螺旋形双苯并沙西因环加合物，并完全控制区域化学和相对立体化学。双苯并氧杂环丙烷是两个连续的逆电子需求环加成过程的结果，二烯对双亲二烯体的立体定向方法。最终产品的螺旋形结构通过光谱证明并通过单晶 X 射线分析证实。
• [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。
• 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.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