N-[5-(8-azidooct-1-ylaminocarbonyl)pent-1-yl]biotinamide | 1587712-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N-[5-(8-azidooct-1-ylaminocarbonyl)pent-1-yl]biotinamide
• 英文别名: 6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-N-(8-azidooctyl)hexanamide
• CAS: 1587712-96-6
• 化学式: C₂₄H₄₃N₇O₃S
• 分子量: 509.717
• InChiKey: SVYZTHMWSYKAKZ-JTAQYXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-二甲基胺-2-丙炔 、 N-[5-(8-azidooct-1-ylaminocarbonyl)pent-1-yl]biotinamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 以73%的产率得到
  参考文献：
  名称：

  Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions

  摘要：

  We studied 1,3,5-triazine-based amide-forming reactions that are mediated or catalyzed by various tert-amines. The representative tert-amine was trimethylamine, which has amido, 1,2,3-triazolyl, aryl, and alkyl linkers. It was found that electron-deficient aryl and heteroaryl linkers, particularly 1,2,3-triazolyl linkers, are superior. On the basis of our findings, we synthesized ligand catalysts, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and found that fluorescent-labeling of a targeting protein using the ligand catalysts proceeded in good yields.

  DOI：

  10.1021/jo500376m
• 作为产物：
  描述：

  8-叠氮-1-辛胺 、 N-生物素己酸 在 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 甲醇 为溶剂， 以30%的产率得到N-[5-(8-azidooct-1-ylaminocarbonyl)pent-1-yl]biotinamide
  参考文献：
  名称：

  Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions

  摘要：

  We studied 1,3,5-triazine-based amide-forming reactions that are mediated or catalyzed by various tert-amines. The representative tert-amine was trimethylamine, which has amido, 1,2,3-triazolyl, aryl, and alkyl linkers. It was found that electron-deficient aryl and heteroaryl linkers, particularly 1,2,3-triazolyl linkers, are superior. On the basis of our findings, we synthesized ligand catalysts, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and found that fluorescent-labeling of a targeting protein using the ligand catalysts proceeded in good yields.

  DOI：

  10.1021/jo500376m

文献信息

• Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions
  作者：Masanori Kitamura、Fumitaka Kawasaki、Kouichi Ogawa、Shuichi Nakanishi、Hiroyuki Tanaka、Kohei Yamada、Munetaka Kunishima

  DOI：10.1021/jo500376m

  日期：2014.4.18

  We studied 1,3,5-triazine-based amide-forming reactions that are mediated or catalyzed by various tert-amines. The representative tert-amine was trimethylamine, which has amido, 1,2,3-triazolyl, aryl, and alkyl linkers. It was found that electron-deficient aryl and heteroaryl linkers, particularly 1,2,3-triazolyl linkers, are superior. On the basis of our findings, we synthesized ligand catalysts, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and found that fluorescent-labeling of a targeting protein using the ligand catalysts proceeded in good yields.