tert-butyl (2R,3R,4R,1'R)-3-amino-4-(tert-butoxycarbonylaminomethyl)-2-methyl-1-(1-phenylethyl)pyrrolidine-3-carboxylate | 1559077-19-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl (2R,3R,4R,1'R)-3-amino-4-(tert-butoxycarbonylaminomethyl)-2-methyl-1-(1-phenylethyl)pyrrolidine-3-carboxylate
• CAS: 1559077-19-8
• 化学式: C₂₄H₃₉N₃O₄
• 分子量: 433.591
• InChiKey: HKZIEABDSGDJDS-CFDUCQJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.89
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R,4R,1'R)-3-amino-4-(tert-butoxycarbonylaminomethyl)-2-methyl-1-(1-phenylethyl)pyrrolidine-3-carboxylate 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、500.01 kPa 条件下， 反应 18.0h， 以99%的产率得到tert-butyl (2R,3R,4S)-3-amino-4-(tert-butoxycarbonylaminomethyl)-2-methylpyrrolidine-3-carboxylate
  参考文献：
  名称：

  Asymmetric Domino Aza-Michael Addition/[3 + 2] Cycloaddition Reactions as a Versatile Approach to α,β,γ-Triamino Acid Derivatives

  摘要：

  Nonproteinogenic amino acids are prepared by an unprecedented domino aza-Michael addition-1,3-dipolar cycloaddition, leading to enantiopure highly substituted pyrrolidinopyrazolines. Nonaflyl azide serves as highly effective diazo transfer reagent, forming the link between the conjugate addition and cycloaddition steps. The resulting pyrrolidinopyrazolines can be rapidly transformed to either alpha,beta,gamma-triamino acids or 3,4-methano-beta-prolines. Peptide coupling can be regioselectively conducted at each of the amino groups.

  DOI：

  10.1021/ol403660w
• 作为产物：
  描述：

  (R)-(+)-N-烯丙基-α-甲基苄胺 在 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -78.0~50.0 ℃ 、1.0 MPa 条件下， 反应 2.58h， 生成 tert-butyl (2R,3R,4R,1'R)-3-amino-4-(tert-butoxycarbonylaminomethyl)-2-methyl-1-(1-phenylethyl)pyrrolidine-3-carboxylate 、 tert-butyl (1R,5S,8R,1'R)-3-(tert-butoxycarbonyl)-8-methyl-7-(1-phenylethyl)-2,3,7-triazabicyclo[3.3.0]octane-1-carboxylate
  参考文献：
  名称：

  Asymmetric Domino Aza-Michael Addition/[3 + 2] Cycloaddition Reactions as a Versatile Approach to α,β,γ-Triamino Acid Derivatives

  摘要：

  Nonproteinogenic amino acids are prepared by an unprecedented domino aza-Michael addition-1,3-dipolar cycloaddition, leading to enantiopure highly substituted pyrrolidinopyrazolines. Nonaflyl azide serves as highly effective diazo transfer reagent, forming the link between the conjugate addition and cycloaddition steps. The resulting pyrrolidinopyrazolines can be rapidly transformed to either alpha,beta,gamma-triamino acids or 3,4-methano-beta-prolines. Peptide coupling can be regioselectively conducted at each of the amino groups.

  DOI：

  10.1021/ol403660w