N-(2-hydroxy-5-methylphenylthio)phthalimide | 178161-09-6

• 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: N-(2-hydroxy-5-methylphenylthio)phthalimide
• 英文别名: 2-(2-hydroxy-5-methylphenylsulfanyl)isoindole-1,3-dione；2-(2-Hydroxy-5-methylphenyl)sulfanylisoindole-1,3-dione
• CAS: 178161-09-6
• 化学式: C₁₅H₁₁NO₃S
• 分子量: 285.323
• InChiKey: WEYYLUKZGQUCNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N-(2-hydroxy-5-methylphenylthio)phthalimide 、 苊烯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以91%的产率得到6-methyl-2,3-dihydroacenaphthene[1,4]benzoxathiin
  参考文献：
  名称：

  [4+2] Cycloadditions of o-Thioquinones with Alkynes and Arylalkenes: a Facile Synthesis of Benzoxathiins

  摘要：

  o-Thioquinones generated in situ from o-hydroxybenzothiophthalimides underwent facile [4+2] cycloaddition reaction with alkynes and alkenes to afford benzoxathiin derivatives.

  DOI：

  10.3987/com-01-s(k)6
• 作为产物：
  描述：

  二硫代邻苯二甲酰亚胺 在 吡啶 、 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 N-(2-hydroxy-5-methylphenylthio)phthalimide
  参考文献：
  名称：

  An internal oxidant-directing strategy enabling transition metal-free C–S bond ligation

  摘要：

  Organic sulfur compounds have broad applications in biology, medicine and material sciences and intensive efforts have been devoted to developing mild and general C-S bond-forming methods. However, a mild, transition-metal-free, direct C-H bond functionalization method remains elusive. Here, we report the use of an internal oxidant-directing strategy to achieve this goal. The cascade reactions described here show excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. This study enlarges the synthesis toolbox for preparing structurally diverse sulfilimines under mild conditions. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.05.021

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。
• 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。
• 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
• Nair, Vijay; Mathew, Bini; Radhakrishnan, Synlett, 2000, # 1, p. 61 - 62
  作者：Nair, Vijay、Mathew, Bini、Radhakrishnan、Rath, Nigam P.

  DOI：——

  日期：——