N-苄基单氮杂-21-冠-7 | 205248-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基单氮杂-21-冠-7
• 英文名称: 1-benzyl-1-aza-21-crown-7
• 英文别名: 19-Benzyl-1,4,7,10,13,16-hexaoxa-19-azacyclohenicosane
• CAS: 205248-60-8
• 化学式: C₂₁H₃₅NO₆
• mdl: MFCD00357533
• 分子量: 397.512
• InChiKey: YAJSCZVHRSWEFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-苄基单氮杂-21-冠-7 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以85%的产率得到1,4,7,10,13,16-六氧杂-19-氮杂环二十一烷
  参考文献：
  名称：

  Effect of crown ether ring size on binding and fluorescence response to saxitoxin in anthracylmethyl monoazacrown ether chemosensors

  摘要：

  介绍了制备不同尺寸的单氮杂蒽甲基冠醚化学传感器（15-冠-5、18-冠-6、21-冠-7、24-冠-8 和 27-冠-9）的便捷大环化合成路线。将这些冠醚作为沙司毒素的化学传感器进行评估后发现，较大的冠醚具有较高的结合常数，其中 27-Crown-9 化学传感器的结合常数最大（2.29 × 105 (mol/L)-1）。当沙士毒素浓度为 5 µmol/L 时，荧光增强率为 100%，接近小鼠生物测定的检测限。

  DOI：

  10.1139/v06-093
• 作为产物：
  描述：

  羟丙基淀粉磷酸酯 在 cesium chloride 、 四丁基溴化铵 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 21.5h， 生成 N-苄基单氮杂-21-冠-7
  参考文献：
  名称：

  Synthesis of monoazacrown ethers under phase-transfer catalysis

  摘要：

  A procedure has been proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol) bis-p-toluenesulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzylaza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr2, and CsCl, respectively, to the reaction mixture, which probably indicated template effect.

  DOI：

  10.1134/s1070428012100156

文献信息

• Effect of crown ether ring size on binding and fluorescence response to saxitoxin in anthracylmethyl monoazacrown ether chemosensors
  作者：Hua Mao、John B Thorne、Jennifer S Pharr、Robert E Gawley

  DOI：10.1139/v06-093

  日期：2006.10.1

  Convenient macrocyclization synthetic routes for the preparation of different-sized monoaza anthracylmethyl crown ether chemosensors (15-crown-5, 18-crown-6, 21-crown-7, 24-crown-8, and 27-crown-9) are described. Evaluation of these crowns as chemosensors for saxitoxin revealed that the larger crowns have moderately higher binding constants, with the 27-crown-9 chemosensor having the largest binding constant (2.29 × 10⁵ (mol/L)^–1). Fluorescence enhancements of 100% were observed at saxitoxin concentrations of 5 µmol/L, which is close to the detection limit in mouse bioassay.Key words: anthracene, crown ethers, saxitoxin, paralytic shellfish poison (PSP), binding constants; chemosensors.

  介绍了制备不同尺寸的单氮杂蒽甲基冠醚化学传感器（15-冠-5、18-冠-6、21-冠-7、24-冠-8 和 27-冠-9）的便捷大环化合成路线。将这些冠醚作为沙司毒素的化学传感器进行评估后发现，较大的冠醚具有较高的结合常数，其中 27-Crown-9 化学传感器的结合常数最大（2.29 × 105 (mol/L)-1）。当沙士毒素浓度为 5 µmol/L 时，荧光增强率为 100%，接近小鼠生物测定的检测限。
• Synthesis of monoazacrown ethers under phase-transfer catalysis
  作者：N. G. Luk’yanenko、S. S. Basok、E. Yu. Kulygina、T. Yu. Bogashchenko、I. S. Yakovenko

  DOI：10.1134/s1070428012100156

  日期：2012.10

  A procedure has been proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol) bis-p-toluenesulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzylaza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr2, and CsCl, respectively, to the reaction mixture, which probably indicated template effect.
• The role of the size of aza-crown recognition moiety in azaphthalocyanine fluorescence sensors for alkali and alkaline earth metal cations
  作者：Lukas Lochman、Jan Svec、Jaroslav Roh、Veronika Novakova

  DOI：10.1016/j.dyepig.2015.05.020

  日期：2015.10

  A series of fluorescence sensors bearing one 1-aza-12-crown-4, 1-aza-15-crown-5, 1-aza-18-crown-6 or 1-aza-21-crown-7 as a recognition moiety and an aza-analogue of phthalocyanine as a fluorophore was prepared. All compounds absorbed and emitted light in the red region. Sensing properties based on intramolecular charge transfer were studied via absorption and fluorescence titration experiments with alkali metal cations and alkaline earth metal cations. Important relationships between aza-crown size and binding affinity were observed in the group of alkali metal cations. Affinity for lithium decreased in series from the smallest crown to the largest, 1-aza-15-crown-5 bound sodium and potassium similarly, and 1-aza-18-crown-6 had the highest affinity to potassium. Alkaline earth metal cations were bound more tightly, which was obvious from more pronounced changes in the absorption spectra, and from the higher increase of fluorescence upon cation addition. A limited size preference was observed in the group of alkaline earth metal cations. (C) 2015 Elsevier Ltd. All rights reserved.