4-benzyl-7-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-[1,4,7]triazonane-1-carbaldehyde | 366815-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-benzyl-7-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-[1,4,7]triazonane-1-carbaldehyde
• 英文别名: 1-benzyl-4-formyl-7-propylphthalimido-1,4,7-triazacyclononane
• CAS: 366815-53-4
• 化学式: C₂₅H₃₀N₄O₃
• 分子量: 434.538
• InChiKey: BHFKVJGKGXYEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.17
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-benzyl-7-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-[1,4,7]triazonane-1-carbaldehyde 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 4-(3-Amino-propyl)-7-benzyl-[1,4,7]triazonane-1-carbaldehyde
  参考文献：
  名称：

  Synthesis of Novel Derivatives of 1,4,7-Triazacyclononane

  摘要：

  [GRAPHICS]The coordination environment of 1,4,7-triazacyclononane can be adapted, through sequential functionalization of two secondary amines, to generate ligands applicable in biomimetic studies. Two "amino acids" and an amino derivative have been prepared from 1,4,7-triazatricyclo-[5.2.1.0(4,10)]decane. This synthon allows efficient attachment of one functional group to the macrocyclic ring, forming a monoamidinium salt. Hydrolysis generates a formyl derivative, which was further functionalized at the secondary amino and hydrolyzed in strong acid to generate ligands 1-3.

  DOI：

  10.1021/ol016291d
• 作为产物：
  描述：

  1-benzyl-4,7-diaza-1-azoniatricyclo[5.2.1.0^4,10]decane bromide 在 水 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 76.0h， 生成 4-benzyl-7-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-[1,4,7]triazonane-1-carbaldehyde
  参考文献：
  名称：

  Synthesis of Novel Derivatives of 1,4,7-Triazacyclononane

  摘要：

  [GRAPHICS]The coordination environment of 1,4,7-triazacyclononane can be adapted, through sequential functionalization of two secondary amines, to generate ligands applicable in biomimetic studies. Two "amino acids" and an amino derivative have been prepared from 1,4,7-triazatricyclo-[5.2.1.0(4,10)]decane. This synthon allows efficient attachment of one functional group to the macrocyclic ring, forming a monoamidinium salt. Hydrolysis generates a formyl derivative, which was further functionalized at the secondary amino and hydrolyzed in strong acid to generate ligands 1-3.

  DOI：

  10.1021/ol016291d

文献信息

• Double Selective Synthetic Approach to the N-Functionalized 1,4,7-Triazacyclononane Derivatives: Chelating Compounds for Controllable Protein Orientation
  作者：Tomasz D. Sobieściak、Piotr Zielenkiewicz

  DOI：10.1021/jo902504d

  日期：2010.3.19

  The double selective synthetic approach is proposed for easy preparation of asymmetrically N-substituted derivatives of 1,4,7-triazacyclononane (tacn, [9]aneN3) with the same or different pendant arms. The synthetic routes simplify the synthesis of “tacn” ligands for functionalization of other carboxy terminated molecules/supports and also facilitate access to azamacrocycle functionalized self-assembled

  提出了双选择性合成方法，以易于制备具有相同或不同侧链的1,4,7-三氮杂环壬烷（tacn，[9] aneN 3）的不对称N-取代的衍生物。合成途径简化了“ tacn”配体的合成，以使其他羧基封端的分子/支持物官能化，并且还促进了氮杂大环官能化的自组装单层（SAMs）或纳米模式的获得，以进行特异性和稳定的组氨酸标记的蛋白质固定。