(3S)-1-benzyl-5-oxopyrrolidine-2,3-diyl diacetate | 870716-22-6

• 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: (3S)-1-benzyl-5-oxopyrrolidine-2,3-diyl diacetate
• 英文别名: (3S)-1-Benzyl-5-oxopyrrolidine-2,3-diyl diacetate；[(3S)-2-acetyloxy-1-benzyl-5-oxopyrrolidin-3-yl] acetate
• CAS: 870716-22-6
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: XPFXNHRDXARQRN-CFMCSPIPSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  446.3±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-1-benzyl-5-oxopyrrolidine-2,3-diyl diacetate 在 iron(III) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以97%的产率得到(4S)-1-benzyl-4,5-dihydroxypyrrolidin-2-one
  参考文献：
  名称：

  自动串联催化：通过 N-Acyliminium 离子化学通过分子间铁催化的酰胺炔基化/水合级联反应获得功能化酮的廉价和绿色途径

  摘要：

  自串联催化：铁 (III) 催化剂被证明可有效催化各种烷氧基、乙酰氧基内酰胺和羟基内酰胺的分子间炔化反应。这种化学反应通过突出铁盐σ-刘易斯酸度的新方面来拓宽铁催化的范围。更重要的是，这种方法适用于前所未有的串联分子间炔基化/分子内水合序列，可以方便地获得新的羰基结构。

  DOI：

  10.1002/chem.202102357

文献信息

• Metal-Catalyzed Cycloisomerization Reactions of <i>cis</i>-4-Hydroxy-5-alkynylpyrrolidinones and <i>cis</i>-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-<i>b</i>]pyrroles and Furo[3,2-<i>b</i>]pyridines
  作者：Jasmine C. Jury、Nalivela Kumara Swamy、Arife Yazici、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1021/jo9007942

  日期：2009.8.7

  Furo[3,2-b]pyrroles and furo[3,2-b]pyridines can be conveniently prepared in good yields from the cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones, respectively, using Ag(I), Pd(II)/Cu(I), or Au(I) catalysis. In one case, the cycloisomerization product was unstable and produced a furan derivative by a ring-opening reaction.

  顺式-4-羟基-5-炔基吡咯烷酮与顺式-5-羟基-6-炔基哌啶子酮的环异构化反应可方便地以高收率制备呋喃并[3,2- b ]吡咯和呋喃[3,2- b ]吡啶分别使用Ag（I），Pd（II）/ Cu（I）或Au（I）催化。在一种情况下，环异构化产物不稳定并且通过开环反应产生呋喃衍生物。
• <i>N</i>-Trialkylsilyl Bistrifluoromethanesulfonimides (R₃SiNTf₂) Are Powerful Catalysts for the Highly Efficient α-Amido Alkylation Reactions of Silicon-Based Nucleophiles
  作者：Raja Ben Othman、Till Bousquet、Mohamed Othman、Vincent Dalla

  DOI：10.1021/ol052357j

  日期：2005.11.1

  In situ formed N-trialkylsilyl bistrifluoromethanesulforlimides (R3SiNTf2) species have been shown to efficiently catalyze the nucleophilic substitution reactions of chiral 5-oxypyrrolidin-2-ones by silicon-based nucleophiles. The reaction rates were significantly accelerated in comparison to the cases where the usual triflate catalysts are used. Adducts were obtained in high yields and usual stereoselectivities within short reaction times, and the process was compatible with a semipreparative scale.
• Addition of a Chiral Boron Enolate to Cyclic <i>N</i>-Acyliminium Ions. Stereocontrolled Synthesis of the Pyrrolizidine Ring System
  作者：Ronaldo A. Pilli、Dennis Russowsky

  DOI：10.1021/jo9513020

  日期：1996.1.1
• Autotandem Catalysis: Inexpensive and Green Access to Functionalized Ketones by Intermolecular Iron‐Catalyzed Amidoalkynylation/Hydration Cascade Reaction via <i>N</i> ‐Acyliminium Ion Chemistry
  作者：Sidi Mohamed Abdallahi、Ewies F. Ewies、Mohamed El‐Shazly、Brahim Ould Elemine、Abderrahmane Hadou、Ján Moncol、Ata Martin Lawson、Adam Daich、Mohamed Othman

  DOI：10.1002/chem.202102357

  日期：2021.11.5

  intermolecular alkynylation reactions of various alkoxy, acetoxylactams, and hydroxylactams. This chemistry broadens the scope of iron catalysis by highlighting new aspects of iron salts σ-Lewis acidity. More importantly, this approach is amenable to an unprecedented tandem intermolecular alkynylation/intramolecular hydration sequence affording expedient access to a new carbonyl structures.

  自串联催化：铁 (III) 催化剂被证明可有效催化各种烷氧基、乙酰氧基内酰胺和羟基内酰胺的分子间炔化反应。这种化学反应通过突出铁盐σ-刘易斯酸度的新方面来拓宽铁催化的范围。更重要的是，这种方法适用于前所未有的串联分子间炔基化/分子内水合序列，可以方便地获得新的羰基结构。