(5RS)-N-(tert-butoxycarbonyl)-5-[(SR)-(2-methoxyphenylamino)(phenyl)methyl]-1H-pyrrol-2(5H)one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5RS)-N-(tert-butoxycarbonyl)-5-[(SR)-(2-methoxyphenylamino)(phenyl)methyl]-1H-pyrrol-2(5H)one
• 英文别名: (R*)-(1-tert-butoxycarbonyl)-5-{(S*)-[(2-methoxyphenyl)amino](phenyl)methyl}-1H-pyrrol-2(5H)-one；tert-butyl (2R)-2-[(S)-(2-methoxyanilino)-phenylmethyl]-5-oxo-2H-pyrrole-1-carboxylate
• 化学式: C₂₃H₂₆N₂O₄
• 分子量: 394.47
• InChiKey: ORPYZOFVSKHBRS-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5RS)-N-(tert-butoxycarbonyl)-5-[(SR)-(2-methoxyphenylamino)(phenyl)methyl]-1H-pyrrol-2(5H)one 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 以98%的产率得到tert-butyl (R)-2-((S)-((2-methoxyphenyl)amino)(phenyl)methyl)-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines

  摘要：

  Pyrrole-based silyl dienolates undergo asymmetric vinylogous Mukaiyama Mannich reactions with a series of N-aryl aldimines in the presence of the Hoveyda-Snapper amino acid-derived silver(I) catalysts. The Manrdch products alpha,beta-unsaturated delta-ammo-gamma-butyrolactams-are typically obtained in high yields, excellent gamma-site selectivities and anti-diastereoselectivities, and up to 80% enantioselectivity.

  DOI：

  10.1021/jo1021234
• 作为产物：
  描述：

  邻甲氧基苯胺 在 N-[2-PPh₂-benzylidene]-L-tert-leucine (4-methoxyphenyl)amide 、 silver(I) acetate 、 异丙醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 (5RS)-N-(tert-butoxycarbonyl)-5-[(SR)-(2-methoxyphenylamino)(phenyl)methyl]-1H-pyrrol-2(5H)one 、 (5S)-N-(tert-butoxycarbonyl)-5-[(R)-(2-methoxyphenylamino)(phenyl)methyl]-1H-pyrrol-2(5H)one
  参考文献：
  名称：

  anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines

  摘要：

  Pyrrole-based silyl dienolates undergo asymmetric vinylogous Mukaiyama Mannich reactions with a series of N-aryl aldimines in the presence of the Hoveyda-Snapper amino acid-derived silver(I) catalysts. The Manrdch products alpha,beta-unsaturated delta-ammo-gamma-butyrolactams-are typically obtained in high yields, excellent gamma-site selectivities and anti-diastereoselectivities, and up to 80% enantioselectivity.

  DOI：

  10.1021/jo1021234

文献信息

• Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates
  作者：Andrea Sartori、Luca Dell'Amico、Claudio Curti、Lucia Battistini、Giorgio Pelosi、Gloria Rassu、Giovanni Casiraghi、Franca Zanardi

  DOI：10.1002/adsc.201100572

  日期：2011.12

  A catalyst-free, environmentally benign three-component vinylogous Mukaiyama–Mannich reaction of pyrrole-based silyl dienolates is presented, which works effectively in both aqueous and solvent-free environments. Both lipophilic and hydrophilic aldehyde candidates are suitable substrates, allowing access to a rich repertoire of unsaturated vicinal aminolactam structures with virtually complete γ-site

  提出了一种无催化剂，对环境无害的三组分乙烯基吡咯基甲硅烷基二烯酸酯的Mukaiyama-Mannich反应，该反应在水性和无溶剂环境中均有效。亲脂性和亲水性醛候选人是合适的基材，使几乎完全γ-部位选择性访问不饱和邻氨基内酰胺结构的丰富剧目，并以较好的抗-diastereoselectivity。该技术的实用性通过保护密集的羟基化糖相关内酰胺框架的无基团合成而得到强调。证明了水作为必不可少的氢键反应推进剂的作用。
• <i>anti</i>-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich Reactions of Pyrrole-Based Silyl Dienolates with <i>N</i>-Aryl Aldimines
  作者：Claudio Curti、Lucia Battistini、Beatrice Ranieri、Giorgio Pelosi、Gloria Rassu、Giovanni Casiraghi、Franca Zanardi

  DOI：10.1021/jo1021234

  日期：2011.4.1

  Pyrrole-based silyl dienolates undergo asymmetric vinylogous Mukaiyama Mannich reactions with a series of N-aryl aldimines in the presence of the Hoveyda-Snapper amino acid-derived silver(I) catalysts. The Manrdch products alpha,beta-unsaturated delta-ammo-gamma-butyrolactams-are typically obtained in high yields, excellent gamma-site selectivities and anti-diastereoselectivities, and up to 80% enantioselectivity.