N-(3,4-dichlorophenylthio)phthalimide | 1227479-84-6

• 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-(3,4-dichlorophenylthio)phthalimide
• 英文别名: 2-(3,4-dichlorophenylsulfanyl)isoindole-1,3-dione；2-(3,4-Dichlorophenyl)sulfanylisoindole-1,3-dione
• CAS: 1227479-84-6
• 化学式: C₁₄H₇Cl₂NO₂S
• 分子量: 324.187
• InChiKey: NAMGYSGWZZFFHL-UHFFFAOYSA-N

物化性质

• 熔点：
  165-169 °C
• 沸点：
  490.9±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dichlorophenylthio)phthalimide 、 1,3-dihydro-1-hydroxy-6-(pyrrol-1-yl)-2,1-benzoxaborole 在 magnesium bromide ethyl etherate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以13.3%的产率得到6-(2-(3,4-dichlorophenylsulfanyl)pyrrol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
  参考文献：
  名称：

  Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei

  摘要：

  Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 mu g/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure activity relationship of the pyrrolobenzoxaboroles are also discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.079
• 作为产物：
  描述：

  3,4-二氯苯硫酚 在 氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 0.5h， 生成 N-(3,4-dichlorophenylthio)phthalimide
  参考文献：
  名称：

  Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei

  摘要：

  Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 mu g/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure activity relationship of the pyrrolobenzoxaboroles are also discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.079

文献信息

• Development of a Kilogram-Scale Asymmetric Synthesis of a Potent DP Receptor Antagonist
  作者：Matthew Tudge、Cecile G. Savarin、Katherine DiFelice、Peter Maligres、Guy Humphrey、Bob Reamer、David M. Tellers、Dave Hughes

  DOI：10.1021/op100008m

  日期：2010.7.16

  characterized by a novel intramolecular Friedel−Crafts cyclization of an imino-pyrrole to prepare the azaindole core. Other key steps include a highly selective Horner−Wadsworth−Emmons olefination of a tricyclic ketone intermediate and subsequent catalytic asymmetric hydrogenation of a trisubstituted α,β-unsaturated ester to install the chirogenic center. Finally, a new indole sulfenylation protocol

  描述了独特的亚磺酰化前列腺素DP受体拮抗剂候选物的有效不对称合成。该合成的特征在于亚氨基吡咯的新型分子内Friedel-Crafts环化反应，以制备氮杂吲哚核。其他关键步骤包括三环酮中间体的高选择性Horner-Wadsworth-Emmons烯化反应以及随后的三取代α，β-不饱和酯的催化不对称氢化以安装色原性中心。最后，开发了新的吲哚亚磺酰化方案，以高收率安装了芳族硫醚官能团。