tert-Butyl 1,4,7-triazonan-1-ylacetate | 174137-99-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-Butyl 1,4,7-triazonan-1-ylacetate
• 英文别名: tert-butyl 2-(1,4,7-triazonan-1-yl)acetate
• CAS: 174137-99-6
• 化学式: C₁₂H₂₅N₃O₂
• 分子量: 243.349
• InChiKey: ASXRRCSNWSZWHO-UHFFFAOYSA-N

物化性质

• 沸点：
  347.4±32.0 °C(predicted)
• 密度：
  0.973±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl 1,4,7-triazonan-1-ylacetate 在 盐酸 作用下， 反应 31.0h， 生成
  参考文献：
  名称：

  Synthesis and Characterization of 1,4,7-Triazacyclononane Derivatives with Methylphosphinate and Acetate Side Chains for Monitoring Free Mg^II by ³¹P and ¹H NMR Spectroscopy

  摘要：

  A series of 1,4,7-triazacyclononane-based ligands containing one, two, or three methylphosphinate (MP) side chains has been prepared, The macrocycle with three methylphosphinates, NOTMP, appeared to be a very promising ligand for monitoring Mg-II in biological samples by P-31 NMR spectroscopy, The P-31 resonances of the free ligand and the Mg-II complex were well resolved, in slow exchange, and well downfield of typical tissue phosphate and phosphate ester metabolite resonances. The K-d value of the Mg(NOTMP) complex was 0.35 mM at physiological pH and temperature, a value which is optimal for accurate assessment of free Mg-II in cells and blood plasma. The latter was confirmed experimentally. Furthermore, the selectivity of NOTMP for Mg-II over Ca-II exceeded 2 orders of magnitude. The K-d values of the Mg-II complexes were sensitive to pH and temperature. The pH effects could be easily predicted from potentiometric pH titration data. Examination of the Mg-II ligand equilibria by P-31 NMR over a wide temperature range provided complexation enthalpies and entropies, It was shown that the smaller K-d values at higher temperatures were largely due to a temperature effect on the highest ligand protonation constant. Only a small endothermic complexation enthalpy contributed to this phenomenon.

  DOI：

  10.1021/ja953771p
• 作为产物：
  描述：

  在 Pd/C (30%) 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以100%的产率得到tert-Butyl 1,4,7-triazonan-1-ylacetate
  参考文献：
  名称：

  N，N，N取代的1,4,7-三氮杂环壬烷的高效合成

  摘要：

  通过调节中间体1,4,7-三苄基-1,4,7-三氮杂-2-2,6-二酮的反应顺序和条件，制备了一系列N，N，N-取代的1,4,7-三氮杂环壬烷用LiAlH 4还原，用Pd / C除去苄基，并烷基化。

  DOI：

  10.1002/ejoc.201800048

文献信息

• A general synthesis of mono- and disubstituted 1,4,7-triazacyclononanes
  作者：Zoltan Kovacs、A. Dean Sherry

  DOI：10.1016/0040-4039(95)02009-e

  日期：1995.12

  1,4,7-Triazacyclononane reacts selectively with 2-(t-butoxycarbonyloxyimino)- and 2-(benzyloxycarbonyloxyimino)-2-phenylacetonitrile to give 1,4-diprotected derivatives which could be converted to mono and disubstituted triazacyclononanes.

  1,4,7-三氮杂环壬烷与2-（叔丁氧羰基氧基亚氨基）-和2-（苄氧羰基氧基亚氨基）-2-苯基乙腈选择性反应，生成1,4-二保护的衍生物，可将其转化为单和二取代的三氮杂环壬烷。
• Efficient synthesis and evaluation of bimodal ligand NETA
  作者：Hyun-Soon Chong、Hyun A. Song、Noah Birch、Thien Le、Sooyoun Lim、Xiang Ma

  DOI：10.1016/j.bmcl.2008.03.084

  日期：2008.6

  The efficient and short synthetic route to the structurally novel bimodal ligand NETA for antibody-targeted radiation therapy (radioimmunotherapy, RIT) of cancer was developed. The structure of NETA was determined by X-ray crystallography. The arsenazo-based UV spectroscopic complexation kinetics data suggest that NETA is a promising chelator for use in RIT applications of (212)Bi, (213)Bi, and (177)Lu. (c) 2008 Published by Elsevier Ltd.
• [EN] METHODS FOR DIAGNOSIS AND TREATMENT OF PULMONARY HYPERTENSION<br/>[FR] MÉTHODES DE DIAGNOSTIC ET DE TRAITEMENT DE L'HYPERTENSION PULMONAIRE
  申请人：[en]THE METHODIST HOSPITAL SYSTEM

  公开号：WO2024025991A1

  公开（公告）日：2024-02-01

  A method is disclosed of detecting a disease associated with pulmonary vascular remodeling in a subject. The method can comprise administering to the subject a compound of Formula I or Formula II. The method can further comprise imaging the compound in lungs of the subject using positron emission tomography to determine uptake of the compound in pulmonary vasculature of the lungs, wherein retention of the compound in the pulmonary vasculature reflects vascular remodeling. Methods of treating a disease associated with pulmonary vascular remodeling or for imaging a pulmonary vasculature in a subject are also provided.
• An Efficient Synthesis of <i>N</i> ,<i>N</i> ,<i>N</i> -Substituted 1,4,7-Triazacyclononane
  作者：Yong Huang、Yajing Liu、Song Liu、Renbo Wu、Zehui Wu

  DOI：10.1002/ejoc.201800048

  日期：2018.4.9

  A series of N,N,N‐substituted 1,4,7‐triazacyclononanes were prepared by adjusting the reaction sequences and conditions of the intermediate 1,4,7‐tribenzyl‐1,4,7‐triazonane‐2,6‐dione reduction with LiAlH4, the removal of benzyl with Pd/C, and alkylation.

  通过调节中间体1,4,7-三苄基-1,4,7-三氮杂-2-2,6-二酮的反应顺序和条件，制备了一系列N，N，N-取代的1,4,7-三氮杂环壬烷用LiAlH 4还原，用Pd / C除去苄基，并烷基化。
• Synthesis and Characterization of 1,4,7-Triazacyclononane Derivatives with Methylphosphinate and Acetate Side Chains for Monitoring Free Mg^II by ³¹P and ¹H NMR Spectroscopy
  作者：Jurriaan Huskens、A. Dean Sherry

  DOI：10.1021/ja953771p

  日期：1996.1.1

  A series of 1,4,7-triazacyclononane-based ligands containing one, two, or three methylphosphinate (MP) side chains has been prepared, The macrocycle with three methylphosphinates, NOTMP, appeared to be a very promising ligand for monitoring Mg-II in biological samples by P-31 NMR spectroscopy, The P-31 resonances of the free ligand and the Mg-II complex were well resolved, in slow exchange, and well downfield of typical tissue phosphate and phosphate ester metabolite resonances. The K-d value of the Mg(NOTMP) complex was 0.35 mM at physiological pH and temperature, a value which is optimal for accurate assessment of free Mg-II in cells and blood plasma. The latter was confirmed experimentally. Furthermore, the selectivity of NOTMP for Mg-II over Ca-II exceeded 2 orders of magnitude. The K-d values of the Mg-II complexes were sensitive to pH and temperature. The pH effects could be easily predicted from potentiometric pH titration data. Examination of the Mg-II ligand equilibria by P-31 NMR over a wide temperature range provided complexation enthalpies and entropies, It was shown that the smaller K-d values at higher temperatures were largely due to a temperature effect on the highest ligand protonation constant. Only a small endothermic complexation enthalpy contributed to this phenomenon.