acetic acid (2S,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester | 1193217-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: acetic acid (2S,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester
• 英文别名: [(2S,3S)-1-benzyl-5-oxo-2-prop-2-enylpyrrolidin-3-yl] acetate
• CAS: 1193217-92-3
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: STYCOUAAVDRNSQ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  acetic acid (2S,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 在 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 以90%的产率得到(4S,5S)-1-benzyl-4-hydroxy-5-prop-2-enylpyrrolidin-2-one
  参考文献：
  名称：

  Nonracemic Bicyclic Lactam Lactones via Regio- and cis-Diastereocontrolled C−H Insertion. Asymmetric Synthesis of (8S,8aS)-Octahydroindolizidin-8-ol and (1S,8aS)-Octahydroindolizidin-1-ol

  摘要：

  The Rh-2(MPPIM)(4)-catalyzed intraniolecular C-H insertion reaction of (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one and (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one proceeds with high regioselectivity and cis-diastereoselectivity to give good yields of chiral nonracemic bicyclic lactam lactones (BLLs). For (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one, the regio selectivity of the C-H insertion is catalyst-dependent; for example, (S)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one undergoes C-H insertion at C-6 preferentially when Rh-2(5S-MPPIM)(4) is used, but with Rh-2(5R-MPPIM)(4), C-H insertion occurs preferentially at C-4. This effect is not observed in the reaction of (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one. The utility of the BLLs as chiral building blocks in alkaloid synthesis is exemplified by the synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

  DOI：

  10.1021/jo901790g
• 作为产物：
  描述：

  acetic acid (2S,3S)-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester 在 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 吡啶 为溶剂， 反应 4.0h， 生成 acetic acid (2S,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester
  参考文献：
  名称：

  由（S）-苹果酸合成他汀类药物；通过自由基环化进行立体控制

  摘要：

  （S）-苹果酸对映体纯的γ-氨基酸他汀和4-表位他汀的高度立体选择性合成分别通过分子内α-酰基氨基自由基反应和分子间N-酰基丙烯基硅烷偶联来描述。

  DOI：

  10.1016/s0040-4039(00)92639-x

文献信息

• <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.
• Toward Improving the Chemistry of <i>N</i>-Acyliminium Ions:  Nucleophilic Substitution Reactions of Pyrrolidinone Derivatives with Trialkylsilyl Nucleophiles Catalyzed by Triisopropylsilyltrifluoromethane Sulfonate (TIPSOTf)
  作者：Raja Ben Othman、Till Bousquet、Anthony Fousse、Mohamed Othman、Vincent Dalla

  DOI：10.1021/ol050576z

  日期：2005.7.1

  Nucleophilic substitution reactions of racemic and chiral 5-acetoxy-, 5-ethoxy-, and 5-methoxypyrrolidin-2-ones by silicon-based nucleophiles were efficiently catalyzed by TIPSOTf. This process was found to be general and accommodates a broad range of substrate-nucleophile combinations.