1-((S)-1-Naphthalen-1-yl-ethyl)-pyrrole-2,5-dione | 188401-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((S)-1-Naphthalen-1-yl-ethyl)-pyrrole-2,5-dione
• 英文别名: 1-[(1S)-1-naphthalen-1-ylethyl]pyrrole-2,5-dione
• CAS: 188401-84-5
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: MWQWRMRLEJOIFK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((S)-1-Naphthalen-1-yl-ethyl)-pyrrole-2,5-dione 在 五羰基溴化锰(I) 、 ammonium acetate 、 氧气 作用下， 以 乙酸乙酯 为溶剂， 反应 21.0h， 生成 3-hydroxy-1-((S)-1-(naphthalen-1-yl)ethyl)-3-(3-phenylquinoxalin-2-yl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  通过 EnT 启用的单线态 O2 添加到 C3-马来酰亚胺化喹喔啉中光诱导产生氧化四元中心：一种无试剂方法

  摘要：

  通过光响应性 C3-马来酰亚胺化喹喔啉的受阻三级羟基化 (C sp3 -H) 和分子内螺醚化 (C sp 3 -H/C sp 2 -H) 实现无试剂、无敏化剂光诱导接触含氧中心已被证明。这是互变异构反应底物诱导的单线态氧吸收发散光氧化的说明性实例，通过使用合适的溶剂引导。

  DOI：

  10.1002/chem.202400219
• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 在 sodium acetate 、 乙酸酐 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 1-((S)-1-Naphthalen-1-yl-ethyl)-pyrrole-2,5-dione
  参考文献：
  名称：

  Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines

  摘要：

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00473-9

文献信息

• Mn(I)-Catalyzed Preferential Electrophilic C3-Maleimidation in Quinoxaline Leading to Spirocyclization and Dehydrogenation of Succinimides
  作者：Subhendu Ghosh、Tamanna Khandelia、Pritishree Panigrahi、Raju Mandal、Bhisma K. Patel

  DOI：10.1021/acs.orglett.3c01350

  日期：2023.5.26

  A Mn(I)-catalyzed site-selective nondirected C3-maleimidation of quinoxaline is established. Herein, the electrophilic C3-metalation precedes over the o-directed strategy to access diversely substituted quinoxaline-appended succinimides. The products undergo PIFA-promoted C(sp2)–C(sp3) spirocyclization via π-electrons drifting from aryls and Selectfluor-mediated dehydrogenation of succinimide at room

  建立了 Mn(I) 催化的喹喔啉位点选择性非定向 C3-马来酰亚胺化反应。在此，亲电子 C3 金属化优先于o定向策略，以获得不同取代的喹喔啉附加琥珀酰亚胺。产物在室温下通过从芳基漂移的 π 电子和 Selectfluor 介导的琥珀酰亚胺脱氢作用，经历 PIFA 促进的 C(sp 2 )–C(sp 3 ) 螺环化。
• Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines
  作者：Kyohei Tokioka、Satoshi Masuda、Tomomi Fujii、Yasuo Hata、Yukio Yamamoto

  DOI：10.1016/s0957-4166(96)00473-9

  日期：1997.1

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.
• 10.1002/chem.202400219
  作者：Ghosh, Subhendu、Khandelia, Tamanna、Mahadevan, Anjali、Panigrahi, Pritishree、Kumar, Piyush、Mandal, Raju、Boruah, Deepjyoti、Venkataramani, Sugumar、Patel, Bhisma K.

  DOI：10.1002/chem.202400219

  日期：——

  A reagent-less sensitizer-free photo-induced access of oxygenated centers via hindered tertiary hydroxylation (Csp3-H) and intramolecular spiro-etherification (Csp3-H/Csp2-H) of photo-responsive C3-maleimidated quinoxaline has been demonstrated. This is an illustrative example of a tautomeric reacting substrate-induced singlet oxygen up-taken divergent photo-oxygenation, guided by the use of a suitable

  通过光响应性 C3-马来酰亚胺化喹喔啉的受阻三级羟基化 (C sp3 -H) 和分子内螺醚化 (C sp 3 -H/C sp 2 -H) 实现无试剂、无敏化剂光诱导接触含氧中心已被证明。这是互变异构反应底物诱导的单线态氧吸收发散光氧化的说明性实例，通过使用合适的溶剂引导。