monoaza-27-crown-9 | 120638-58-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: monoaza-27-crown-9
• 英文别名: 1-aza-27-crown-9；1,4,7,10,13,16,19,22-Octaoxa-25-azacycloheptacosane；1,4,7,10,13,16,19,22-octaoxa-25-azacycloheptacosane
• CAS: 120638-58-6
• 化学式: C₁₈H₃₇NO₈
• 分子量: 395.494
• InChiKey: UOANWNHFIFDAHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  85.9
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  monoaza-27-crown-9 、 4-溴甲基苯甲醛 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以94%的产率得到4-(1,4,7,10,13,16,19,22-Octaoxa-25-azacycloheptacos-25-ylmethyl)benzaldehyde
  参考文献：
  名称：

  Visible Fluorescence Chemosensor for Saxitoxin

  摘要：

  Absorption spectra of a number of shellfish extracts have been obtained and reveal prominent absorptions in all samples at 210 and 260 nm and at 325 nm in some of them. These absorptions preclude the use of chromophores with similar absorptions in testing of shellfish samples for paralytic shellfish toxins. Two crown ether chemosensors featuring a boron azadipyrrin chromophore have been synthesized; both have absorption maxima at 650 nm, where all the shellfish extracts are transparent. The synthetic sensors feature either 18- or 27-membered crown ether rings and have been evaluated as visible sensors for the paralytic shellfish toxin saxitoxin. The binding constant for one of them is in the range of 3-9 x 10(5) M-1 and exhibits a fluorescence enhancement of over 100% at 680 nm in the presence of 40 mu M saxitoxin.

  DOI：

  10.1021/jo062506r
• 作为产物：
  描述：

  七乙二醇二对甲苯磺酸酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 monoaza-27-crown-9
  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

文献信息

• Visible Fluorescence Chemosensor for Saxitoxin
  作者：Robert E. Gawley、Hua Mao、M. Mahbubul Haque、John B. Thorne、Jennifer S. Pharr

  DOI：10.1021/jo062506r

  日期：2007.3.1

  Absorption spectra of a number of shellfish extracts have been obtained and reveal prominent absorptions in all samples at 210 and 260 nm and at 325 nm in some of them. These absorptions preclude the use of chromophores with similar absorptions in testing of shellfish samples for paralytic shellfish toxins. Two crown ether chemosensors featuring a boron azadipyrrin chromophore have been synthesized; both have absorption maxima at 650 nm, where all the shellfish extracts are transparent. The synthetic sensors feature either 18- or 27-membered crown ether rings and have been evaluated as visible sensors for the paralytic shellfish toxin saxitoxin. The binding constant for one of them is in the range of 3-9 x 10(5) M-1 and exhibits a fluorescence enhancement of over 100% at 680 nm in the presence of 40 mu M saxitoxin.
• 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。