1-<(4-Methoxyphenyl)methylthio>-2,5-pyrrolidindion | 57624-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-<(4-Methoxyphenyl)methylthio>-2,5-pyrrolidindion
• 英文别名: N-(p-Methoxybenzylthio)-succinimid；N-(p-methoxybenzyl)sulfanylsuccinimide；1-[(4-Methoxyphenyl)methylsulfanyl]pyrrolidine-2,5-dione
• CAS: 57624-27-8
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: PQHCRRGCZATQGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<(4-Methoxyphenyl)methylthio>-2,5-pyrrolidindion 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 p-Methoxybenzyl-hydrodisulfid
  参考文献：
  名称：

  对位取代苄基氢二硫化物及相关化合物的合成及核磁共振谱

  摘要：

  合成标题化合物并测量它们的NMR谱。苄基氢二硫化物的化学位移与σ或σR无关，而相应硫醇的化学位移与σ有关。

  DOI：

  10.1246/bcsj.48.2993

文献信息

• Organocatalytic Asymmetric α-Sulfenylation of 2-Substituted Indolin-3-ones: A Strategy for the Synthesis of Chiral 2,2-Disubstituted Indole-3-ones with S- and N-Containing Heteroquaternary Carbon Stereocenter
  作者：Yong-Long Zhao、Xing-Hai Fei、Yong-Qin Tang、Peng-Fei Xu、Fen-Fen Yang、Bin He、Xiao-Zhong Fu、Yuan-Yong Yang、Meng Zhou、Yuan-Hu Mao、Yong-Xi Dong、Chun Li

  DOI：10.1021/acs.joc.9b01142

  日期：2019.6.21

  An organocatalytic asymmetric α-sulfenylation of 2-substituted indolin-3-ones with N-(alkylthio or arylthio)succinimides has been developed for the first time using Cinchona-derived squaramide as the catalyst. Various chiral 2,2-disubstituted indole-3-ones with S- and N-containing heteroquaternary carbon stereocenters were obtained with up to 98% yield and 99% ee.

  用金鸡纳衍生的方酰胺作为催化剂，首次开发了具有N-（烷硫基或芳硫基）琥珀酰亚胺的2-取代的吲哚-3-酮的有机催化不对称α-亚磺酰基。获得了具有含S和N的杂季碳碳立体中心的各种手性2，2-二取代的吲哚-3-酮，产率高达98％，ee高达99％。
• Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines
  作者：Nicolas R. Koning、Anders P. Sundin、Daniel Strand

  DOI：10.1021/jacs.1c10364

  日期：2021.12.22

  natural products. Herein, we report the first total syntheses of (−)-glionitrin A/B and revise the absolute configurations. Emerging from the study is a novel oxidative sulfenylation of triketopiperazines that enables asymmetric formation of dithiodiketopiperazines on sensitive substrates. The concise route paves the way for further studies on the potent antimicrobial and antitumor activities of glionitrin

  在其他非手性支架上不对称构建二硫代二酮哌嗪仍然是许多具有生物学意义的天然产物中遇到的关键合成挑战。在此，我们报告了 (-)-glionitrin A/B 的首次全合成并修改了绝对构型。该研究产生了一种新的三酮哌嗪氧化亚磺酰化，可以在敏感底物上不对称地形成二硫代二酮哌嗪。简洁的路线为进一步研究 glionitrin A 的强效抗菌和抗肿瘤活性以及 glionitrin B 抑制癌细胞侵袭能力的有趣能力铺平了道路。
• Dartmann, Mechthild; Flitsch, Wilhelm; Krebs, Bernt, Liebigs Annalen der Chemie, 1988, p. 695 - 704
  作者：Dartmann, Mechthild、Flitsch, Wilhelm、Krebs, Bernt、Pandl, Klaus、Westfechtel, Alfred

  DOI：——

  日期：——
• Enantioselective organocatalytic α-sulfenylation of substituted diketopiperazines
  作者：Nathan W. Polaske、Ramin Dubey、Gary S. Nichol、Bogdan Olenyuk

  DOI：10.1016/j.tetasy.2009.10.037

  日期：2009.12

  The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported. (C) 2009 Elsevier Ltd. All rights reserved.