(S)-N-(2-butynyl)-(1-phenylethyl)amine | 1344918-70-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-(2-butynyl)-(1-phenylethyl)amine
• 英文别名: N-[(1S)-1-phenylethyl]but-2-yn-1-amine
• CAS: 1344918-70-2
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: NYQBARABEMNJGA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-butynyl)-(1-phenylethyl)amine 在 吡啶 、 氢气 作用下， 生成 (S)-(-)-N-(1-phenylethyl)butylamine 、 (Z,S)-N-(2-butenyl)-(1-phenylethyl)amine 、 N-<(S)-1-phenyleth-1-yl>-N-<2(E)-buten-1-yl>amine
  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：

  (S)-(-)- α-甲基苄胺 、 1-溴-2-丁炔 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以57%的产率得到(S)-N-(2-butynyl)-(1-phenylethyl)amine
  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

文献信息

• Asymmetric Domino Aza-Michael Addition/[3 + 2] Cycloaddition Reactions as a Versatile Approach to α,β,γ-Triamino Acid Derivatives
  作者：Vojtěch Kapras、Radek Pohl、Ivana Císařová、Ullrich Jahn

  DOI：10.1021/ol403660w

  日期：2014.2.21

  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.