(S)-2-carbonylbenzyloxy-9-formyl-1,3,4,9-tetrahydro-β-carboline-3-carboxylic acid | 475296-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-carbonylbenzyloxy-9-formyl-1,3,4,9-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: (3S)-9-formyl-2-phenylmethoxycarbonyl-3,4-dihydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS: 475296-64-1
• 化学式: C₂₁H₁₈N₂O₅
• 分子量: 378.384
• InChiKey: NESUBZWKQIVKEC-SFHVURJKSA-N

物化性质

• 沸点：
  652.9±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 (S)-2-carbonylbenzyloxy-9-formyl-1,3,4,9-tetrahydro-β-carboline-3-carboxylic acid 以 乙醚 为溶剂， 生成 (S)-2-carbonylbenzyloxy-9-formyl-1,3,4,9-tetrahydro-β-carboline-3-carboxylic acid tert-butylammonium salt
  参考文献：
  名称：

  N-甲基天冬酰胺，精氨酸，组氨酸和色氨酸的新型合成。

  摘要：

  [反应：见正文]肽中的N-甲基氨基酸残基修饰了几个药理上有用的参数，但由于N-甲基化单体的缺乏，烷基化肽的合成受到了阻碍。提出了具有碱性侧链的四个N-甲基氨基酸的合成。这些碱性氨基酸的侧链需要特别保护或构建。这完成了我们小组通过5-恶唑烷酮中间体制备的20种常见L-氨基酸N-甲基衍生物的集合。

  DOI：

  10.1021/ol026799w
• 作为产物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 在 三乙基硅烷 、 camphor-10-sulfonic acid 、 三乙胺 、 三氟乙酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 49.5h， 生成 (S)-2-carbonylbenzyloxy-9-formyl-1,3,4,9-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of N-Methyl Amino Acids by Way of Intermediate 5-Oxazolidinones

  摘要：

  N-Methyl amino acids occur in many natural products. Experimental strategies are presented for a unified approach to the synthesis of N-methyl derivatives through 5-oxazolidinones of the 20 common L-amino acids. The amino acids with reactive side chains that required protecting groups or devoted syntheses for side chain construction for N-methylation to proceed included serine, threonine, tyrosine, cysteine, methionine, tryptophan, asparagine, histidine, and arginine. The studies have provided improved methods for the preparation of N-methyl serine, threonine, and tyrosine. All 20 of the common L-amino acids are now available in suitable forms for solid or solution-phase peptide synthesis.

  DOI：

  10.1021/jo026722l

文献信息

• A Novel Synthesis of <i>N</i>-Methyl Asparagine, Arginine, Histidine, and Tryptophan
  作者：Luigi Aurelio、Robert T. C. Brownlee、Andrew B. Hughes

  DOI：10.1021/ol026799w

  日期：2002.10.1

  [reaction: see text] N-Methyl amino acid residues in peptides modify several pharmacologically useful parameters, but synthesis of alkylated peptides is hampered by unavailability of N-methylated monomers. The syntheses of four N-methyl amino acids with basic side chains are presented. The side chains of these basic amino acids needed to be specially protected or constructed. This completes the set

  [反应：见正文]肽中的N-甲基氨基酸残基修饰了几个药理上有用的参数，但由于N-甲基化单体的缺乏，烷基化肽的合成受到了阻碍。提出了具有碱性侧链的四个N-甲基氨基酸的合成。这些碱性氨基酸的侧链需要特别保护或构建。这完成了我们小组通过5-恶唑烷酮中间体制备的20种常见L-氨基酸N-甲基衍生物的集合。
• An Efficient Synthesis of <i>N</i>-Methyl Amino Acids by Way of Intermediate 5-Oxazolidinones
  作者：Luigi Aurelio、John S. Box、Robert T. C. Brownlee、Andrew B. Hughes、Marianne M. Sleebs

  DOI：10.1021/jo026722l

  日期：2003.4.1

  N-Methyl amino acids occur in many natural products. Experimental strategies are presented for a unified approach to the synthesis of N-methyl derivatives through 5-oxazolidinones of the 20 common L-amino acids. The amino acids with reactive side chains that required protecting groups or devoted syntheses for side chain construction for N-methylation to proceed included serine, threonine, tyrosine, cysteine, methionine, tryptophan, asparagine, histidine, and arginine. The studies have provided improved methods for the preparation of N-methyl serine, threonine, and tyrosine. All 20 of the common L-amino acids are now available in suitable forms for solid or solution-phase peptide synthesis.