deamino-Nle(N3)-Phe-Ala-Tyr(prop-2-ynyl)-OMe | 1301627-81-5

• 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: deamino-Nle(N3)-Phe-Ala-Tyr(prop-2-ynyl)-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-[[(2S)-2-(6-azidohexanoylamino)-3-phenylpropanoyl]amino]propanoyl]amino]-3-(4-prop-2-ynoxyphenyl)propanoate
• CAS: 1301627-81-5
• 化学式: C₃₁H₃₈N₆O₆
• 分子量: 590.679
• InChiKey: COZLMOAQBHLUHT-CAVYSCNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  deamino-Nle(N3)-Phe-Ala-Tyr(prop-2-ynyl)-OMe 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以85%的产率得到methyl (15S,18S,21S)-15-benzyl-18-methyl-13,16,19-trioxo-2-oxa-5,6,7,14,17,20-hexazatricyclo[21.2.2.14,7]octacosa-1(26),4(28),5,23(27),24-pentaene-21-carboxylate
  参考文献：
  名称：

  CuAAC Macrocyclization: High Intramolecular Selectivity through the Use of Copper–Tris(triazole) Ligand Complexes

  摘要：

  A range of multivalent heteroaryl ligands, copper sources, and solvent systems have been Investigated for use in CuAAC-mediated macrocyclization reactions. These studies have revealed the key factors governing selectivity for macrocyclization versus dimerization and identified a simple but specific set of reaction conditions capable of efficiently generating a diverse series of drug-like macrocycles at modest dilution in up to 95% yield.

  DOI：

  10.1021/ol200861f
• 作为产物：
  描述：

  6-溴己酸乙酯 在 N-甲基吗啉 、 sodium azide 、 N-羟基-7-氮杂苯并三氮唑 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 0.08h， 生成 deamino-Nle(N3)-Phe-Ala-Tyr(prop-2-ynyl)-OMe
  参考文献：
  名称：

  CuAAC Macrocyclization: High Intramolecular Selectivity through the Use of Copper–Tris(triazole) Ligand Complexes

  摘要：

  A range of multivalent heteroaryl ligands, copper sources, and solvent systems have been Investigated for use in CuAAC-mediated macrocyclization reactions. These studies have revealed the key factors governing selectivity for macrocyclization versus dimerization and identified a simple but specific set of reaction conditions capable of efficiently generating a diverse series of drug-like macrocycles at modest dilution in up to 95% yield.

  DOI：

  10.1021/ol200861f

文献信息

• CuAAC Macrocyclization: High Intramolecular Selectivity through the Use of Copper–Tris(triazole) Ligand Complexes
  作者：Gagan Chouhan、Keith James

  DOI：10.1021/ol200861f

  日期：2011.5.20

  A range of multivalent heteroaryl ligands, copper sources, and solvent systems have been Investigated for use in CuAAC-mediated macrocyclization reactions. These studies have revealed the key factors governing selectivity for macrocyclization versus dimerization and identified a simple but specific set of reaction conditions capable of efficiently generating a diverse series of drug-like macrocycles at modest dilution in up to 95% yield.