1-ethyl-1,4,7,10-tetraazacyclododecane | 216100-96-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-ethyl-1,4,7,10-tetraazacyclododecane
• 英文别名: 1-ethyl-4,7,10-tetraazacyclododecane；1-ethylcyclen；1-Ethyl-1,4,7,10-tetrazacyclododecane
• CAS: 216100-96-8
• 化学式: C₁₀H₂₄N₄
• 分子量: 200.327
• InChiKey: QDCBLIKFCXTNJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 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：

  N-异丙基氯乙酰氨 、 1-ethyl-1,4,7,10-tetraazacyclododecane 在 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以41%的产率得到2-[7-ethyl-4,10-bis(isopropylcarbamoylmethyl)-1,4,7,10-tetraazacyclododec-1-yl]-N-isopropylacetamide
  参考文献：
  名称：

  Belousoff, Matthew J.; Ung, Phuc; Forsyth, Craig M., Journal of the American Chemical Society, 2009, vol. 131, p. 1106 - 1114

  摘要：

  DOI：
• 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-ethyl-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

• NEW GADOLINIUM CHELATE COMPOUNDS FOR USE IN MAGNETIC RESONANCE IMAGING
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3611169A1

  公开（公告）日：2020-02-19

  The present invention relates to a new class of high relaxivity extracellular gadolinium chelate complexes, to methods of preparing said compounds, and to the use of said compounds as MRI contrast agents.

  本发明涉及一类新的高弛豫性细胞外钆螯合物、制备所述化合物的方法以及将所述化合物用作核磁共振成像造影剂。
• 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.
• Selective Mono- and 1,4-Di-N-alkylations of 1,4,7,10-Tetraazacyclododecane.
  作者：Zhi Li、Kjell Undheim、Jan-Eric Berg、Charlotta Damberg、Inger Wahlberg、Luis Juliá、Ola Persson

  DOI：10.3891/acta.chem.scand.52-1247

  日期：——

  General methods for selective N-alkylations of the macrocycle 1,4,7,10-tetraazacyclododecane have been developed. The N-monoalkylation proceeds via a cyclic guanidinium derivative, and the regioselective 1,4-N,N-dialkylation via a cyclic amidinium derivative. All transformations were high yield reactions.
• TARGETED DELIVERY TO BETA CELLS
  申请人：THE BROAD INSTITUTE , INC.

  公开号：US20200384115A1

  公开（公告）日：2020-12-10

  The disclosure includes zinc prodrugs for targeted delivery of therapeutic, diagnostic or imaging agents to β-cells and methods of use therefor. The disclosure also includes targeted delivery of small molecules to β-cells that stabilize and activate CRISPR effector proteins comprising at least one destabilization domain, to enable CRISPR-based genome editing and transcriptional activation or repression in β-cells.