N-(2-chlorophenylthio)phthalimide | 1615684-89-3

• 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-chlorophenylthio)phthalimide
• 英文别名: 2-((2-chlorophenyl)thio)isoindoline-1,3-dione；2-(2-Chlorophenyl)sulfanylisoindole-1,3-dione
• CAS: 1615684-89-3
• 化学式: C₁₄H₈ClNO₂S
• 分子量: 289.742
• InChiKey: SVTXSDSTKHZNNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：

  1,3-dihydro-1-hydroxy-6-(pyrrol-1-yl)-2,1-benzoxaborole 、 N-(2-chlorophenylthio)phthalimide 在 magnesium bromide ethyl etherate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以11.7%的产率得到6-(2-(2-chlorophenylsulfanyl)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：

  邻氯苯硫酚 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-(2-chlorophenylthio)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

• Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to <i>N</i> ‐Acylsulfenamides
  作者：Zhaoxin Wei、Renjie Wang、Yonghong Zhang、Bin Wang、Yu Xia、Ablimit Abdukader、Fei Xue、Weiwei Jin、Chenjiang Liu

  DOI：10.1002/ejoc.202100924

  日期：2021.9.7

  A variety of N-acylsulfenamides are produced by the electrochemically enabled cross-coupling of readily available feedstocks under standard conditions. This protocol is practical and has wide substrate scope with good reaction efficiency (38 examples, up to 97 % yield). A possible free radical mechanism is preliminarily demonstrated.

  在标准条件下，通过电化学使容易获得的原料进行交叉偶联，可以生产多种N-酰基亚磺酰胺。该方案实用性强，底物范围广，反应效率高（38个例子，产率高达97%）。初步证明了一种可能的自由基机制。
• Hydrochloric Acid-Promoted Intermolecular 1,2-Thiofunctionalization of Aromatic Alkenes
  作者：Xiaomeng Li、Yunlong Guo、Zengming Shen

  DOI：10.1021/acs.joc.7b03263

  日期：2018.3.2

  and different types of nucleophiles. Importantly, extension of nucleophiles can reach aryl ethers, indoles, and carboxylic acids with good reactivity. This practical and convenient method has broad substrate scope and high yields under metal-free and mild conditions. Furthermore, we achieved conversion and application for making sulfoxide and sulfone by oxidation.

  开发了一种通过芳族烯烃的双官能化制备1,2-硫代官能化产物的有效方法。在这种方法中，廉价和容易获得的盐酸被用于促进N-芳基亚硫基邻苯二甲酰亚胺和不同类型亲核试剂对芳基烯烃的1,2-硫官能化。重要的是，亲核试剂的延伸可以达到具有良好反应性的芳基醚，吲哚和羧酸。该实用方便的方法在无金属和温和条件下具有宽泛的基材范围和高产率。此外，我们实现了氧化转化为亚砜和砜的转化和应用。
• Metal-free and site-selective α-C–H functionalization of tetrahydrofuran enabled by the photocatalytic generation of bromine radicals
  作者：Can-Ming Zhu、Rong-Bin Liang、Yonghong Xiao、Wei Zhou、Qing-Xiao Tong、Jian-Ji Zhong

  DOI：10.1039/d2gc03347j

  日期：——

  A simple and inherent green photocatalytic approach using commercially available and cheap ⁿBu₄NBr with 4-CzIPN was reported to effectively initiate the site-selective α-C(sp³)-H activation of tetrahydrofuran for C-S and C-C cross-couplings.

  一种简单且固有的绿色光催化方法，利用商业可得且价格便宜的nBu4NBr和4-CzIPN，能够有效地启动四氢呋喃的位点选择性α-C(sp3)-H活化，用于C-S和C-C交叉偶联反应。
• Photoredox Synthesis of Thio‐Functionalized Cyclic Ethers Using <i>N</i>‐Sulfenyl Phthalimides as a Thiyl‐Radical Precursor
  作者：Maojian Lu、Rong‐Bin Liang、Can‐Ming Zhu、Qing‐Xiao Tong、Jian‐Ji Zhong

  DOI：10.1002/cjoc.202300118

  日期：2023.8

  A visible-light mediated exclusively regioselective synthesis of 2,2-disubstituted thio-functionalized tetrahydrofurans, tetrahydro- pyrans and oxepanes has been described through an operationally simple and mild photoredox protocol. Thiyl radical generated from N-phenylsulfenyl phthalimide by photoredox catalysis was proven to be the key reactive intermediate in this reaction.

  通过操作简单且温和的光氧化还原方案描述了可见光介导的 2,2-二取代硫代官能化四氢呋喃、四氢吡喃和氧杂环庚烷的完全区域选择性合成。N-苯基硫基邻苯二甲酰亚胺通过光氧化还原催化产生的硫基自由基被证明是该反应中的关键反应中间体。
• US4231930A
  申请人：——

  公开号：US4231930A

  公开（公告）日：1980-11-04