1-(E)-cinnamylpyrrolidine-2,5-dione | 95607-03-7

• 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-(E)-cinnamylpyrrolidine-2,5-dione
• 英文别名: 1-[(E)-3-phenylprop-2-enyl]pyrrolidine-2,5-dione
• CAS: 95607-03-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: SMNMWVSZHXVRIL-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-(E)-cinnamylpyrrolidine-2,5-dione 在 copper(II) bis(trifluoromethanesulfonate) 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(2-Oxo-3-phenylpropyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  三氟甲磺酸铜(II)催化氨基2,3-环氧化物重排生成α-氨基酮

  摘要：

  使用三氟甲磺酸铜(II)作为催化剂，通过基于生物质的氨基环氧化物的Meinwald重排合成α-氨基酮。重排的区域选择性可以通过最稳定的碳阳离子中间体进行反应来合理化，以中等至良好的收率得到各种α-氨基α'-芳基酮。这是使用良性且廉价的催化剂制备 α-氨基酮的一种有吸引力的方法。

  DOI：

  10.1055/s-0043-1775367
• 作为产物：
  描述：

  丁二酰亚胺 生成 1-(E)-cinnamylpyrrolidine-2,5-dione
  参考文献：
  名称：

  XASEHGAVA, IOSIXIRO;KURIYAMA, TAKASI;SITAMURA, XATSUSI;SUGOI, MITSURO;OKA+

  摘要：

  DOI：

文献信息

• <i>N</i>-Allylation of Imides Catalyzed by Palladium(0)
  作者：Yoshio Inoue、Masaaki Taguchi、Masanori Toyofuku、Harukichi Hashimoto

  DOI：10.1246/bcsj.57.3021

  日期：1984.10

  Palladium(0)–triphenylphosphine complexes catalyzed the allylic exchange reaction of allylic esters, phenyl ethers, and isoureas with imides such as phthalimide to give N-allylic products. Among them, O-allylic isoureas were most effective in exchanging the allylic group of more complex structure. N-Allylic derivatives were also obtained by the telomerization of butadiene or allene with phthalimide

  钯（0）-三苯基膦配合物催化烯丙酯、苯基醚和异脲与酰亚胺（如邻苯二甲酰亚胺）的烯丙基交换反应，得到 N-烯丙基产物。其中，O-烯丙基异脲最有效地交换更复杂结构的烯丙基。N-烯丙基衍生物也可通过丁二烯或丙二烯与邻苯二甲酰亚胺在钯 (0) 物种催化下的调聚反应获得。
• Vinylation of Alkyl Halides Catalyzed by Palladium Catalyst
  作者：Pan Yi、Zhang Zhuangyu、Hu Hongwen

  DOI：10.1080/00397919208021336

  日期：1992.7

  Abstract The palladium catalyzed vinylation of alkyl halides, especially benzyl chlorides, with a variety of olefins has been studied. A possible free radical mechanism was proposed.

  摘要 研究了钯催化烷基卤，特别是苄基氯与多种烯烃的乙烯基化反应。提出了一种可能的自由基机制。
• Tuning the Selectivity of Palladium Catalysts for Hydroformylation and Semihydrogenation of Alkynes: Experimental and Mechanistic Studies
  作者：Jiawang Liu、Zhihong Wei、Ji Yang、Yao Ge、Duo Wei、Ralf Jackstell、Haijun Jiao、Matthias Beller

  DOI：10.1021/acscatal.0c03614

  日期：2020.10.16

  palladium catalyst system for chemodivergent functionalization of alkynes with syngas. In the presence of an advanced ligand L2 bearing 2-pyridyl substituent as a built-in base, either hydroformylation or semihydrogenation of diverse alkynes occurs with high chemo- and stereoselectivity under comparable conditions. Mechanistic studies, including density functional theory (DFT) calculations, kinetic

  在这里，我们描述了一种选择性钯催化剂体系，用于炔烃与合成气的化学扩散功能化。在带有2-吡啶基取代基作为内置碱基的高级配体L2的存在下，各种炔烃的加氢甲酰化或半氢化反应在相当的条件下都具有很高的化学和立体选择性。包括密度泛函理论（DFT）计算，动力学分析和控制实验在内的机理研究表明，酸性助催化剂的强度和浓度在控制化学选择性方面起着决定性的作用。DFT研究表明，配体L2不仅可以在加氢甲酰化的氢解步骤中促进类似于沮丧的路易斯对（FLP）系统的氢的杂化活化，而且可以抑制CO配位以促进强酸条件下的半氢化。这种可切换的选择性为设计用于所需产物的新型催化剂提供了一种策略。
• Fluoride-Catalyzed Addition of PhSCF₂SiMe₃ to <i>N</i>-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of <i>gem</i>-Difluoromethylenated 1-Azabicyclic Compounds
  作者：Teerawut Bootwicha、Duanghathai Panichakul、Chutima Kuhakarn、Samran Prabpai、Palangpon Kongsaeree、Patoomratana Tuchinda、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1021/jo802794u

  日期：2009.5.15

  PhSCF2SiMe3 (1) was found, for the first time, to undergo fluoride-catalyzed nucleophilic difluoro-(phenylsulfanyl)methylation reaction to cyclic imides 2, affording the corresponding adducts 3 in moderate to good yields. Reductive cleavage of the phenylsulfanyl group of N-alkylated adducts 3 with Bu3SnH/AIBN yielded gem-difluoromethylated products 4. Under the same reduction conditions, N-alkenylated and N-alkynylated adducts 3 afforded the corresponding gem-difluoromethylenated 1-azabicyclic compounds 5 and 6 with trans stereoselectivity. These compounds were employed as precursors for preparing substituted gem-difluoromethylenated pyrrolizidinones and indolizidinones 7 and 8 by treatment with Et3SiH/BF3 center dot OEt2, and compounds 9 and 10 by nucleophilic displacement of the hydroxyl group, using organosilanes in the presence of BF3 center dot OEt2. The synthesis of highly substituted gem-difluoromethylenated pyrrolizidines 13 and 14 was also demonstrated.
• INOUE, YOSHIO;TAGUCHI, MASAAKI;TOYOFUKU, MASANORI;HISHIMOTO, HARUKICHI, BULL. CHEM. SOC. JAP., 1984, 57, N 10, 3021-3022
  作者：INOUE, YOSHIO、TAGUCHI, MASAAKI、TOYOFUKU, MASANORI、HISHIMOTO, HARUKICHI

  DOI：——

  日期：——