acetic acid (2S,3S)-2-acetoxy-1-benzyl-5-oxo-pyrrolidin-3-yl ester | 133005-21-7

• 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: acetic acid (2S,3S)-2-acetoxy-1-benzyl-5-oxo-pyrrolidin-3-yl ester
• 英文别名: (4S,5S)-N-benzyl-2,3-diacetoxybutyrolactam；(4S,5S)-4,5-Bis(acetyloxy)-1-(phenylmethyl)-2-pyrrolidinone；[(2S,3S)-2-acetyloxy-1-benzyl-5-oxopyrrolidin-3-yl] acetate
• CAS: 133005-21-7
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: XPFXNHRDXARQRN-ZFWWWQNUSA-N

物化性质

• 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：

  acetic acid (2S,3S)-2-acetoxy-1-benzyl-5-oxo-pyrrolidin-3-yl ester 在 sodium methylate 、 四氯化钛 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (4S,5R)-1-Benzyl-4-hydroxy-5-(2-methyl-allyl)-pyrrolidin-2-one
  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
• 作为产物：
  描述：

  (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 4.25h， 生成 acetic acid (2S,3S)-2-acetoxy-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

• Studies towards the synthesis of (+)-ptilomycalin A; Stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams
  作者：Saskia Louwrier、Martin Ostendorf、Arnoud Boom、Henk Hiemstra、W. Nico Speckamp

  DOI：10.1016/0040-4020(95)01085-8

  日期：1996.2

  Highly stereoselective N-acyliminium ion coupling reactions of β-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.

  报道了β-酮酸酯衍生的甲硅烷基烯醇醚与衍生自（S）-苹果酸的对映体纯内酰胺的高度立体选择性的N-酰亚胺离子偶联反应。这种反应类型适用于对映体C-2取代的内酰胺27的合成，内酰胺27是拟定的Ptilomycalin A合成中可能的中间体。
• Towards Simplifying the Chemistry of<i>N</i>-Acyliminium Ions: A One-Pot Protocol for the Preparation of 5-Acetoxy Pyrrolidin-2-ones and 2-Acetoxy<i>N</i>-Alkoxycarbonyl Pyrrolidines from Imides
  作者：Vincent Dalla、Fridrich Szemes Jr.、Anthony Fousse、Raja Ben Othman、Till Bousquet、Mohamed Othman

  DOI：10.1055/s-2006-926318

  日期：——

  A new one-step protocol for the synthesis of acetoxy lactams starting from imides has been developed. This method involves regiospecific reduction of the imide with LiEt 3 BH, then capture of the transient lithium alkoxide by acetic anhydride.

  已经开发了一种从酰亚胺开始合成乙酰氧基内酰胺的新一步法。该方法包括用 LiEt 3 BH 对酰亚胺进行区域特异性还原，然后用乙酸酐捕获瞬时的醇锂。
• Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst
  作者：Frédéric Pin、Sébastien Comesse、Bernard Garrigues、Štefan Marchalín、Adam Daïch

  DOI：10.1021/jo062077x

  日期：2007.2.1

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).
• 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
• 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.