1-hexyl-4,7,10-tetraazacyclododecane | 767614-85-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-hexyl-4,7,10-tetraazacyclododecane
• 英文别名: 1-Hexyl-1,4,7,10-tetrazacyclododecane
• CAS: 767614-85-7
• 化学式: C₁₄H₃₂N₄
• 分子量: 256.435
• InChiKey: ALPGKWIWCYGBSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  39.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 1-hexyl-4,7,10-tetraazacyclododecane 在 sodium hydroxide 作用下， 反应 48.0h， 以83%的产率得到1-hexyl-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tetrahydrochloride
  参考文献：
  名称：

  Synthesis of Lipophilic Paramagnetic Contrast Agents

  摘要：

  The facile, high-yielding synthesis of a series of macrocycles 7a-k in 75-100% yield is reported. The transformation of these compounds to their carboxymethylated analogues 8a-k in 75-90% yield and subsequent gadolinium complexes 9a-k provides a series of homologous neutral paramagnetic contrast agents (PCAs) with tunable lipophilicity. Alkylated cationic intermediates 6a-k are prepared in yields of 72-94% from glyoxal adduct of cyclen (5) and slight excesses of alkyl iodides. The methodology is selective for monoalkylation and amenable to large-scale synthesis.

  DOI：

  10.1021/jo981920r
• 作为产物：
  描述：

  1-碘己烷 在 氢氧化钾 作用下， 以 甲苯 为溶剂， 反应 192.0h， 生成 1-hexyl-4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Synthesis of Lipophilic Paramagnetic Contrast Agents

  摘要：

  The facile, high-yielding synthesis of a series of macrocycles 7a-k in 75-100% yield is reported. The transformation of these compounds to their carboxymethylated analogues 8a-k in 75-90% yield and subsequent gadolinium complexes 9a-k provides a series of homologous neutral paramagnetic contrast agents (PCAs) with tunable lipophilicity. Alkylated cationic intermediates 6a-k are prepared in yields of 72-94% from glyoxal adduct of cyclen (5) and slight excesses of alkyl iodides. The methodology is selective for monoalkylation and amenable to large-scale synthesis.

  DOI：

  10.1021/jo981920r

文献信息

• Selective mono N-alkylations of cyclen in one step syntheses
  作者：Julien Massue、Sally E. Plush、Célia S. Bonnet、Doireann A. Moore、Thorfinnur Gunnlaugsson

  DOI：10.1016/j.tetlet.2007.09.022

  日期：2007.11

  cyclen (1,4,7,10-tetraazacyclododecane) using a range of functionalized alkyl halides. This ‘easy to use’ synthesis gives rise to mono-derivatives of cyclen from various alkyl halides or, when using alkyl dihalides, bis-cyclen derivatives, where the alkyl group links two cyclen macrocycles together. While the reaction conditions require the use of 1:4 stoichiometry (alkyl halide:cyclen), any unreacted

  在这封信中，我们描述了使用一系列官能化的烷基卤化物进行的环己酮（1,4,7,10-四氮杂环十二烷）的选择性一步单N-烷基化。这种“易于使用”的合成方法产生了由各种卤代烷形成的环素单衍生物，或者，当使用烷基二卤化物时，产生了双环素衍生物，其中烷基将两个环素大环连接在一起。虽然反应条件要求使用化学计量比为1：4（卤代烷：环烷烃），但任何未反应的环糊精都可以通过水萃取法回收并成功地重复使用。发现该方法是非常通用的，特别适合于带有受保护的硫醇基团以及α-氯酰胺衍生的生色团的循环目标。这种细胞周期垂体生色团被用作镧系元素发光探针和传感器的触角。
• Synthesis of Lipophilic Paramagnetic Contrast Agents
  作者：William C. Baker、Michael J. Choi、Daniel C. Hill、Julie L. Thompson、Peter A. Petillo

  DOI：10.1021/jo981920r

  日期：1999.4.1

  The facile, high-yielding synthesis of a series of macrocycles 7a-k in 75-100% yield is reported. The transformation of these compounds to their carboxymethylated analogues 8a-k in 75-90% yield and subsequent gadolinium complexes 9a-k provides a series of homologous neutral paramagnetic contrast agents (PCAs) with tunable lipophilicity. Alkylated cationic intermediates 6a-k are prepared in yields of 72-94% from glyoxal adduct of cyclen (5) and slight excesses of alkyl iodides. The methodology is selective for monoalkylation and amenable to large-scale synthesis.