(Z)-N^α-acetyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-6'-yl)-alanine, methyl ester | 460096-30-4

• 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: (Z)-N^α-acetyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-6'-yl)-alanine, methyl ester
• 英文别名: tert-butyl 6-[(Z)-2-acetamido-3-methoxy-3-oxoprop-1-enyl]indole-1-carboxylate
• CAS: 460096-30-4
• 化学式: C₁₉H₂₂N₂O₅
• 分子量: 358.394
• InChiKey: WSOSONKCCYWQMJ-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-N^α-acetyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-6'-yl)-alanine, methyl ester 在 (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以100%的产率得到(S)-N^α-acetyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-6'-yl)-alanine, methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Protected Tryptophan Regioisomers

  摘要：

  Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation-a interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a-e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.

  DOI：

  10.1021/jo025964i
• 作为产物：
  描述：

  吲哚-6-甲醛 在 potassium tert-butylate 、 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 反应 144.0h， 生成 (Z)-N^α-acetyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-6'-yl)-alanine, methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Protected Tryptophan Regioisomers

  摘要：

  Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation-a interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a-e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.

  DOI：

  10.1021/jo025964i

文献信息

• Catalytic Asymmetric Synthesis of Protected Tryptophan Regioisomers
  作者：Paul R. Carlier、Polo C.-H. Lam、Dawn M. Wong

  DOI：10.1021/jo025964i

  日期：2002.8.1

  Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation-a interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a-e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.