1-((4-fluorobenzyl)thio)pyrrolidine-2,5-dione | 1537899-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((4-fluorobenzyl)thio)pyrrolidine-2,5-dione
• 英文别名: 1-[(4-Fluorophenyl)methylsulfanyl]pyrrolidine-2,5-dione；1-[(4-fluorophenyl)methylsulfanyl]pyrrolidine-2,5-dione
• CAS: 1537899-68-5
• 化学式: C₁₁H₁₀FNO₂S
• 分子量: 239.27
• InChiKey: JYSMBVATLIBTLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-苄基-1,3-二氢-1-甲基-2H-吲哚-2-酮 、 1-((4-fluorobenzyl)thio)pyrrolidine-2,5-dione 在 C₁₁H₂₁N₃ 作用下， 反应 72.0h， 以77%的产率得到(S)-(-)-3-benzyl-3-((4-fluorobenzyl)thio)-1-methylindolin-2-one
  参考文献：
  名称：

  Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of Oxindoles and Benzofuran-2(3H)-ones

  摘要：

  A chiral bicyclic guanidine-catalyzed enantioselective sulfenylation of 3-substituted oxindoles to N-(sulfanyl)-succinimides has been developed. A series of unprecedented 3-sulfenylated oxindoles, such as 3-benzyl/alkyl-substituted 3-benzyl/alkyloxindoles, were obtained with high enantioselectivities (up to 98% ee). This methodology is also effective for the first asymmetric sulfenylation of benzofuran-2(3H)-ones, providing 3-benzyl-3-benzylthio-substituted benzofuran-2(3H)-ones with satisfactory results (up to 95% ee).

  DOI：

  10.1021/acs.joc.5b01606
• 作为产物：
  描述：

  N-氯代丁二酰亚胺 、 4-氟苄基硫醇 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以62%的产率得到1-((4-fluorobenzyl)thio)pyrrolidine-2,5-dione
  参考文献：
  名称：

  邻乙烯基苯胺的催化对映选择性氧亚磺酰化

  摘要：

  Tf 2 NH 辅助的 BINAM 衍生的硫代磷酰胺催化已完成用于邻乙烯基苯胺与N -（芳基/烷硫基）酰亚胺的对映选择性氧亚磺酰化。所开发的反应以优异的产率和对映体比率提供了多种取代的芳基/烷硫基连接的 3,1-苯并恶嗪。此外，还讨论了苯并恶嗪和芳基/烷硫基部分的合成应用以及观察到的对映选择性的过渡态模型。

  DOI：

  10.1039/d1cc05835e

文献信息

• Highly Enantioselective Organocatalytic α-Sulfenylation of Azlactones
  作者：Baokun Qiao、Xinfei Liu、Shaobo Duan、Lin Yan、Zhiyong Jiang

  DOI：10.1021/ol403303k

  日期：2014.2.7

  molecular sieves as an additive. The reaction conditions were suitable to 4-alkyl and benzyl-substituted azlactones as well as N-(benzyl/alkyl/arylthio)succinimides, affording adducts with high enantioselectivities (81–94% ee).

  通过使用金鸡纳生物碱衍生的方酰胺作为催化剂和4Å分子筛作为添加剂，已开发出N -（（硫烷基）琥珀酰亚胺）对内酯进行的首个不对称α-亚磺酰基化反应。反应条件适用于4-烷基和苄基取代的内酯以及N-（苄基/烷基/芳硫基）琥珀酰亚胺，可提供高对映选择性（81-94％ee）的加合物。
• Acid-Promoted Carbosulfenylation of 1,6-Dienes: Selective Synthesis of Dehydropiperidines Scaffolds
  作者：Arunachalam Kesavan、Akshaya Kumar Sahu、Pazhamalai Anbarasan

  DOI：10.1021/acs.orglett.3c01274

  日期：2023.7.7

  employing N-(aryl/alkylthio)succinimides as a thiolating reagent. The reaction involves the generation of an episulfonium ion followed by intramolecular trapping with alkenes, which offers access to diverse thiolated dehydropiperidines in good yield. In addition, the synthesis of dihydropyran and cyclohexene derivatives, as well as the conversion of the arylthiol moiety to useful functional groups, were

  使用N- (芳基/烷硫基)琥珀酰亚胺作为硫醇化试剂，实现了酸催化1,6-二烯硫磺酰化的有效方法。该反应涉及生成表锍离子，然后用烯烃进行分子内捕获，从而以良好的产率获得各种硫醇化脱氢哌啶。此外，还演示了二氢吡喃和环己烯衍生物的合成，以及芳硫醇部分向有用官能团的转化。
• Enantioselective Reduction and Sulfenylation of Isoflavanone Derivatives via Bisguanidinium Hypervalent Silicate
  作者：Qiaoqiang Li、Yuqing Dai、Xinru Xu、Wentao Wu、Wenchao Chen、Hong Wang、Choon-Hong Tan、Xinyi Ye

  DOI：10.1021/acs.orglett.4c02202

  日期：2024.7.26

  In this work, we describe an enantioselective reduction and sulfenylation of isoflavanone derivatives by an ion pair strategy. The chiral cationic catalyst bisguanidinium (BG) is capable of chiral induction in catalytic systems. Silane hydride works as a reductant and helps to form an anionic hypervalent silicate complex and intermediates with substrates to pair with chiral catalyst. A series of umpolung

  在这项工作中，我们描述了通过离子对策略对异黄烷酮衍生物进行对映选择性还原和磺酰化。手性阳离子催化剂双胍 ( BG ) 能够在催化体系中进行手性诱导。硅烷氢化物作为还原剂，有助于与底物形成阴离子超价硅酸盐络合物和中间体，以与手性催化剂配对。一系列的反极性硫试剂在硅酸盐阴离子存在下完成亲电子攻击。化学选择性和对映选择性均从良好到优异，可提供多种 4-oxo-4 H-色烯-3-甲腈和S-亲电子试剂。完成进一步改造以引入更多应用。
• Synthesis of unsymmetrical phosphorus disulfides
  作者：Jeffrey Ash、Jun Yong Kang

  DOI：10.1039/d4ob01099j

  日期：——

  strategy employing N-thiosuccinimides and (EtO)2P(O)SH has been developed to synthesize unsymmetrical organophosphorus disulfides (P(O)–S–S motif). A pronucleophile (EtO)2P(O)SH, Brønsted acid and phosphorothioate nucleophile, converts N-thiosuccinimides into unsymmetrical phosphorus disulfides. This protocol achieves catalyst- and additive-free reaction conditions, uses a renewable solvent (EtOH), and avoids

  采用N-硫代琥珀酰亚胺和(EtO) 2P (O)SH的硫介导的umpolung策略已被开发用于合成不对称有机磷二硫化物（P(O)–S–S基序）。亲核试剂 (EtO) 2 P(O)SH、布朗斯台德酸和硫代磷酸酯亲核试剂，可将N-硫代琥珀酰亚胺转化为不对称的二硫化磷。该方案实现了无催化剂和无添加剂的反应条件，使用可再生溶剂（EtOH），并避免使用刺激性试剂。
• Highly enantioselective α-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides
  作者：Mei Xu、Baokun Qiao、Shaobo Duan、Hongjun Liu、Zhiyong Jiang

  DOI：10.1016/j.tet.2014.09.037

  日期：2014.11

  An unprecedented asymmetric alpha-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides has been established, to access various alpha-sulfenylated adducts with good to excellent enantioselectivities (86-95% ee) by utilizing a cinchona alkaloid-derived squaramide as catalyst. The conditions of this alpha-sulfenylation protocol simultaneously satisfy N-(arylthio)succinimides, N-(benzylthio)succinimides, and N-(alkylthio)succinimides by tuning the substituted groups of 5H-oxazol-4-ones on the 2-position as well as additives. (C) 2014 Elsevier Ltd. All rights reserved.