1-(N-benzyloxycarbonyl ethylamine)-4,7,10-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclotetradecane | 824984-74-9

• 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: 1-(N-benzyloxycarbonyl ethylamine)-4,7,10-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclotetradecane
• 英文别名: 1-[N-(benzyloxycarbonyl)-2-aminoethyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic tris(1,1-dimethylethyl) ester；1-[N-(benzyloxycarbonyl)-2-aminoethyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tri(1,1-dimethylethyl ester)；1-(N-benzyloxycarbonylethylamine)-4,7,10-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane；Tert-butyl 2-[4,7-bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-10-[2-(phenylmethoxycarbonylamino)ethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetate
• CAS: 824984-74-9
• 化学式: C₃₆H₆₁N₅O₈
• 分子量: 691.909
• InChiKey: YHOMHCKVOGMLCC-UHFFFAOYSA-N

物化性质

• 沸点：
  719.3±60.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(N-benzyloxycarbonyl ethylamine)-4,7,10-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclotetradecane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以28.6 g的产率得到1-(2-ethylamine)-4,7,10-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclotetradecane
  参考文献：
  名称：

  Poly-β-cyclodextrin based platform for pH mapping via a ratiometric 19F/1H MRI method

  摘要：

  报道了一种基于超分子聚δ-环糊精â19FâGd加合物的新型 pH 图谱磁共振成像方法的体外验证。

  DOI：

  10.1039/b914540k
• 作为产物：
  描述：

  N-Cbz-2-溴乙胺 、 1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸三叔丁酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以34 g的产率得到1-(N-benzyloxycarbonyl ethylamine)-4,7,10-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclotetradecane
  参考文献：
  名称：

  Poly-β-cyclodextrin based platform for pH mapping via a ratiometric 19F/1H MRI method

  摘要：

  报道了一种基于超分子聚δ-环糊精â19FâGd加合物的新型 pH 图谱磁共振成像方法的体外验证。

  DOI：

  10.1039/b914540k

文献信息

• [EN] SYNTHESIS OF TRIS N-ALKYLATED 1,4,7,10-TETRAAZACYCLODODECANES<br/>[FR] SYNTHESE DE 1,4,7,10-TETRAAZA-CYCLODODECANES TRIS N-ALKYLES
  申请人：UNIV HONG KONG

  公开号：WO2005003105A1

  公开（公告）日：2005-01-13

  A directly synthetic method for preparing tris-alkylated 1,4,7,10-tetraazacyclododecanes by the reactions of 1,4,7,10-tetraazacyclododecane (cyclen) and appropriate electrophiles is accomplished in high yield. The method provides operational convenience, starting material availability, cost economy, atom efficiency and reaction insensitivity to temperature, moisture, and concentrations of starting materials. With this method, the yield of tris-(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane can be 77%, the highest reported. The yield of other tris-N alkylated products can be in the range of 65-84%.

  通过对1,4,7,10-四氮杂环十二烷（cyclen）和适当的亲电试剂反应，实现了一种直接合成三烷基化1,4,7,10-四氮杂环十二烷的方法，收率高。该方法提供操作方便、起始物质易得、成本经济、原子效率高，且对温度、湿度和起始物质浓度的反应不敏感。利用这种方法，三-(叔丁氧羰基甲基)-1,4,7,10-四氮杂环十二烷的产率可达77%，为目前报道的最高。其他三N烷基化产物的产率可在65-84%的范围内。
• Poly-β-cyclodextrin based platform for pH mapping via a ratiometric 19F/1H MRI method
  作者：Eliana Gianolio、Roberta Napolitano、Franco Fedeli、Francesca Arena、Silvio Aime

  DOI：10.1039/b914540k

  日期：——

  The in vitro validation of a new pH mapping MRI method based on a supramolecular poly-β-cyclodextrin–19F–Gd adduct is reported.

  报道了一种基于超分子聚δ-环糊精â19FâGd加合物的新型 pH 图谱磁共振成像方法的体外验证。
• Luminescent heptadentate Tb3+ complex with pendant aza-15-crown-5 showing recognition of lactate and salicylate in aqueous solution
  作者：Cong Li、Wing-Tak Wong

  DOI：10.1016/j.tetlet.2004.06.063

  日期：2004.7

  The coordinatedly unsaturated neutral complex TbL1 that possesses two labile metal-bound water Molecules provides linear response to lactate in the range of 0-3.0 mM at the simulated extracellular background with the variations of Tb luminescence lifetime as output: the maximal amplification of the luminescence intensity of TbL1 reaches a factor of 135 upon titration with aromatic antenna salicylate in the physiological pH window. (C) 2004 Elsevier Ltd. All rights reserved.
• Exofacial Protein Thiols as a Route for the Internalization of Gd(III)-Based Complexes for Magnetic Resonance Imaging Cell Labeling
  作者：Giuseppe Digilio、Valeria Menchise、Eliana Gianolio、Valeria Catanzaro、Carla Carrera、Roberta Napolitano、Franco Fedeli、Silvio Aime

  DOI：10.1021/jm901876r

  日期：2010.7.8

  Four novel MRI Gd(III)-based probes have been synthesized and evaluated for their labeling properties on cultured cell lines K562, C6, and B16. The labeling strategy relies upon the fact that cells display a large number of reactive exofacial protein thiols (EPTs) that can be exploited as anchorage points for suitably activated MRI probes. The probes are composed of a Gd(III) chelate (based on either DO3A or DTPA) connected through a flexible linker to the 2-pyridyldithio chemical function for binding to EPTs. GdDO3A-based chelates could efficiently label cells (up to a level of 1.2 x 10(10) Gd(III) atoms/cell), whereas GdDTPA-based chelates showed poor or no cell labeling ability at all. Among the GdDO3A based compounds, that having the longest spacer (compound GdL1A) showed the best labeling efficacy. The mechanism of EPT mediated cell labeling by GdL1A involves probe internalization without sequestration of the Gd(III) chelate within subcellular structures such as endosomes.