3-benzyl-2-oxo-3-(trifluoroacetamido)-pyrrolidine | 133230-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-benzyl-2-oxo-3-(trifluoroacetamido)-pyrrolidine
• 英文别名: N-(3-benzyl-2-oxo-3-pyrrolidinyl)-2,2,2-trifluoroacetamide；N-(3-benzyl-2-oxopyrrolidin-3-yl)-2,2,2-trifluoroacetamide
• CAS: 133230-45-2
• 化学式: C₁₃H₁₃F₃N₂O₂
• 分子量: 286.254
• InChiKey: VIWJMICSZDPRSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzyl-2-oxo-3-(trifluoroacetamido)-pyrrolidine 在 barium dihydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 3-amino-3-benzylpyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of .alpha.-benzyl .gamma.-lactam, .alpha.-benzyl .delta.-lactam, and .alpha.-benzylproline derivatives as conformationally restricted analogs of phenylalaninamide

  摘要：

  The ready availability of N-(trifluoroacetyl)-alpha-allylphenylalaninamide (4) via a dehydration/hetero-Cope rearrangement/ammonolysis sequence starting with N-(trifluoroacetyl)phenylalanine allyl ester made it an attractive intermediate for elaboration into C-alpha to N- or C-alpha to N'bridged products as conformationally restricted phenylalaninamide analogues. Oxidative one-carbon degradation of the side-chain olefin followed by acid-catalyzed silane reduction afforded C-alpha to N'-bridged gamma-lactam. Hydroboration/oxidation of the side-chain olefin provided an intermediate that could be cyclized selectively either to a delta-lactam or a proline analogue depending on choice of dehydrating conditions. For preparation of a target dipeptide containing the alpha-substituted proline moiety, a preferred route involved N-deprotection of 4 and coupling to Boc-Asp(OBn)-OH to give a dipeptide intermediate, which similarly could be elaborated selectively to either the alpha-benzyl delta-lactam analogue or the alpha-benzylproline analogue.

  DOI：

  10.1021/jo00012a022
• 作为产物：
  描述：

  在 三乙基硅烷 、 ammonium hydroxide 、 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 3-benzyl-2-oxo-3-(trifluoroacetamido)-pyrrolidine
  参考文献：
  名称：

  Synthesis of .alpha.-benzyl .gamma.-lactam, .alpha.-benzyl .delta.-lactam, and .alpha.-benzylproline derivatives as conformationally restricted analogs of phenylalaninamide

  摘要：

  The ready availability of N-(trifluoroacetyl)-alpha-allylphenylalaninamide (4) via a dehydration/hetero-Cope rearrangement/ammonolysis sequence starting with N-(trifluoroacetyl)phenylalanine allyl ester made it an attractive intermediate for elaboration into C-alpha to N- or C-alpha to N'bridged products as conformationally restricted phenylalaninamide analogues. Oxidative one-carbon degradation of the side-chain olefin followed by acid-catalyzed silane reduction afforded C-alpha to N'-bridged gamma-lactam. Hydroboration/oxidation of the side-chain olefin provided an intermediate that could be cyclized selectively either to a delta-lactam or a proline analogue depending on choice of dehydrating conditions. For preparation of a target dipeptide containing the alpha-substituted proline moiety, a preferred route involved N-deprotection of 4 and coupling to Boc-Asp(OBn)-OH to give a dipeptide intermediate, which similarly could be elaborated selectively to either the alpha-benzyl delta-lactam analogue or the alpha-benzylproline analogue.

  DOI：

  10.1021/jo00012a022

文献信息

• HOLLADAY, M. W.;NADZAN, A. M., J. ORG. CHEM., 56,(1991) N2, C. 3900-3905
  作者：HOLLADAY, M. W.、NADZAN, A. M.

  DOI：——

  日期：——
• Synthesis of .alpha.-benzyl .gamma.-lactam, .alpha.-benzyl .delta.-lactam, and .alpha.-benzylproline derivatives as conformationally restricted analogs of phenylalaninamide
  作者：Mark W. Holladay、Alex M. Nadzan

  DOI：10.1021/jo00012a022

  日期：1991.6

  The ready availability of N-(trifluoroacetyl)-alpha-allylphenylalaninamide (4) via a dehydration/hetero-Cope rearrangement/ammonolysis sequence starting with N-(trifluoroacetyl)phenylalanine allyl ester made it an attractive intermediate for elaboration into C-alpha to N- or C-alpha to N'bridged products as conformationally restricted phenylalaninamide analogues. Oxidative one-carbon degradation of the side-chain olefin followed by acid-catalyzed silane reduction afforded C-alpha to N'-bridged gamma-lactam. Hydroboration/oxidation of the side-chain olefin provided an intermediate that could be cyclized selectively either to a delta-lactam or a proline analogue depending on choice of dehydrating conditions. For preparation of a target dipeptide containing the alpha-substituted proline moiety, a preferred route involved N-deprotection of 4 and coupling to Boc-Asp(OBn)-OH to give a dipeptide intermediate, which similarly could be elaborated selectively to either the alpha-benzyl delta-lactam analogue or the alpha-benzylproline analogue.