1-butyl-1,4,7,10-tetraazacyclododecane | 289685-93-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-butyl-1,4,7,10-tetraazacyclododecane
• 英文别名: 1-butyl-4,7,10-tetraazacyclododecane；1-Butyl-1,4,7,10-tetrazacyclododecane
• CAS: 289685-93-4
• 化学式: C₁₂H₂₈N₄
• 分子量: 228.381
• InChiKey: FXNQJNHABNUVBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  3
• 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：

  1-butyl-1,4,7,10-tetraazacyclododecane 、 N,N-diethylacetatochloroacetamide 在 caesium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以42%的产率得到1,4,7-tris-(N,N-bis(ethoxycarbonylmethyl))-10-[butyl]-1,4,7,10 tetraazacyclododecane
  参考文献：
  名称：

  基于环镧系元素的胶束结构，可用作发光[Eu（III）]和磁性[Gd（III）]共振成像（MRI）造影剂

  摘要：

  提出了一种新型的基于Ln（III）的两亲性配合物，具有潜在的发光和MRI造影剂的作用，它们在水溶液中自组装成球形胶束。

  DOI：

  10.1039/c6cc03092k
• 作为产物：
  描述：

  1,4,7-triformyl-cyclen 在 potassium carbonate 作用下， 以 sodium hydroxide 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-butyl-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Expeditious N-monoalkylation of 1,4,7,10-tetraazacyclododecane (cyclen) via formamido protection

  摘要：

  The reaction of cyclen 1 with chloral hydrate afforded exclusively 1,4,7-triformylcyclen 2 in high yield; the triprotected macrocycle was easily alkylated with various electrophiles in good to excellent yields. The alkaline removal of the formyl groups provided a selective entry into N-monosubstituted cyclen derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01092-3

文献信息

• 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.
• Stoichiometric mono N-functionalization of cyclen via a boron protected intermediate
  作者：F Chuburu、M Le Baccon、H Handel

  DOI：10.1016/s0040-4020(01)00115-6

  日期：2001.3

  The temporary triprotection of cyclen by a boron atom performed in presence of sodium hydride offers a convenient solution for the mono N-alkylation of cyclen. Examples of mono N-alkylated cyclens and bis-cyclens are reported. (C) 2001 Elsevier Science Ltd. All rights reserved.
• MACROCYCLIC COMPLEXES, THEIR PROCESS OF PREPARATION AND USE AS PET IMAGING AGENTS
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：US20170210714A1

  公开（公告）日：2017-07-27

  The present invention concerns compounds of formula (I): their process of preparation and compositions thereof. The present invention also concerns their use as diagnostic agent in PET imaging.
• Expeditious N-monoalkylation of 1,4,7,10-tetraazacyclododecane (cyclen) via formamido protection
  作者：Vincenzo Boldrini、Giovanni B Giovenzana、Roberto Pagliarin、Giovanni Palmisano、Massimo Sisti

  DOI：10.1016/s0040-4039(00)01092-3

  日期：2000.8

  The reaction of cyclen 1 with chloral hydrate afforded exclusively 1,4,7-triformylcyclen 2 in high yield; the triprotected macrocycle was easily alkylated with various electrophiles in good to excellent yields. The alkaline removal of the formyl groups provided a selective entry into N-monosubstituted cyclen derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Cyclen lanthanide-based micellar structures for application as luminescent [Eu(<scp>iii</scp>)] and magnetic [Gd(<scp>iii</scp>)] resonance imaging (MRI) contrast agents
  作者：Esther M. Surender、Steve Comby、Sarah Martyn、Brenton Cavanagh、T. Clive Lee、Dermot F. Brougham、Thorfinnur Gunnlaugsson

  DOI：10.1039/c6cc03092k

  日期：——

  Novel Ln(III)-based amphiphilic complexes with potential application as luminescent and MRI contrast agents, which self-assemble in aqueous solution into spherical micelles, are presented.

  提出了一种新型的基于Ln（III）的两亲性配合物，具有潜在的发光和MRI造影剂的作用，它们在水溶液中自组装成球形胶束。