N-(3-bromopropyl)-5-(dimethylamino)-1-naphthalenesulfonamide | 195057-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-bromopropyl)-5-(dimethylamino)-1-naphthalenesulfonamide
• 英文别名: N-(3-bromopropyl)-5-(dimethylamino)naphthalene-1-sulfonamide；N-(3-bromopropyl)dansylamide
• CAS: 195057-92-2
• 化学式: C₁₅H₁₉BrN₂O₂S
• 分子量: 371.298
• InChiKey: DUSXVCZANDDXIT-UHFFFAOYSA-N

物化性质

• 沸点：
  490.9±55.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)-5-(dimethylamino)-1-naphthalenesulfonamide 在 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79.3%的产率得到1-[5-(dimethylamine)naphthalenyl-1-sulfonyl]azetidine
  参考文献：
  名称：

  Synthesis and characterization ofN-arylsulfonylazetidines

  摘要：

  Abstractmagnified imageA convenient method for the synthesis of N‐arylsulfonyl azetidines using N‐(3‐bromopropyl)‐arylsulfonamide with cesium carbonate and potassium iodide in DMF is reported. The reaction conditions are optimized and seven N‐arylsulfonyl azetidines have been synthesized in good yield using this method. The structures of compounds 2a and 2e were determined by X‐ray crystallography.

  DOI：

  10.1002/jhet.5570450449
• 作为产物：
  描述：

  丹酰氯 在 TEA 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 N-(3-bromopropyl)-5-(dimethylamino)-1-naphthalenesulfonamide
  参考文献：
  名称：

  Zn2+ fluorescent chemosensors and the influence of their spacer length on tuning Zn2+ selectivityElectronic supplementary information (ESI) available: job plot, partial 1H NMR spectra of free 3 and the 3–Zn2+ complex, Ca2+ and Mg2+ interference for Zn2+ sensing of 3, Kd measurements, and buffer preparation. See http://www.rsc.org/suppdata/p2/b2/b200462c/

  摘要：

  基于配位增强荧光（CHEF）机制的Zn2+荧光化学传感器被制备出来，并通过控制间隔基长度实现了对Zn2+选择性的精细调节。对金属离子的荧光发射响应显示，Co2+、Cu2+和Ni2+使荧光减弱，而Ca2+、Cd2+和Zn2+使荧光增强。在3号传感器中实现了对Zn2+的最大选择性，优于Ca2+和Cd2+。基本结合特性（化学计量比、表观解离常数和pH依赖性）通过荧光光谱法测量。3号传感器与Zn2+的Job图分析表明形成了1:1的复合物。表观解离常数Kd在pH 7.5时为0.98（±0.43）nM [50 mM HEPES缓冲液，I = 0.1 (NaNO3)]。在pH超过7的区域，2号传感器及其与Zn2+的复合物的荧光强度平稳，表明荧光测量受生理pH变化的影响不大。

  DOI：

  10.1039/b200462c

文献信息

• Direct C-11 functionalisation of anatoxin-a. Application to the synthesis of new ligand-based structural probes
  作者：Nicholas A. Magnus、Laurent Ducry、Valérie Rolland、Susan Wonnacott、Timothy Gallagher

  DOI：10.1039/a702087b

  日期：——

  A variety of methods have been evaluated for the functionalisation of the C-11 methyl group of anatoxin-a. Reaction of N-Boc anatoxin-a 9 with PhI(OH)OTs (Koser’s reagent) represents the method of choice and gives the synthetically versatile α-tosyloxy ketone 10. This intermediate provides a convenient vehicle for the attachment of spacer units to C-11 via a thioether linkage which has been applied to the synthesis of the dansylated [N-(5-dimethylamino-1-naphthylsulfonyl)] anatoxin-a derivatives. Preliminary biological data relating to the α-thiomethyl anatoxin-a derivative 16 and the dansylated ligands, 25 and 26, are also reported.

  评估了多种对锐毒毒素-a 的 C-11 甲基进行官能化的方法。N-Boc 锐毒毒素-a 9 与 PhI(OH)OTs（科塞试剂）的反应是首选方法，可得到合成用途广泛的 α-甲氧基酮 10。这种中间体为通过硫醚连接将间隔单元连接到 C-11 提供了方便的载体，已被用于合成丹酰化的[N-（5-二甲基氨基-1-萘磺酰基）]锐毒毒素-a 衍生物。此外，还报告了与α-硫代甲基锐毒毒素-a 衍生物 16 以及丹酰化配体 25 和 26 有关的初步生物数据。
• Turn-On Fluorescence Sensing of Cyanide Ions in Aqueous Solution at Parts-per-Billion Concentrations
  作者：Youngmin Kim、Hyun-Sue Huh、Min Hyung Lee、Ivan L. Lenov、Haiyan Zhao、François P. Gabbaï

  DOI：10.1002/chem.201002861

  日期：2011.2.11

  A few parts per billion are enough to turn on a novel fluorescent cyanide sensor in aqueous solutions. Because of its inherent electron deficiency, the cationic boron moiety of this sensor not only serves as a high‐affinity anion binding site, but also quenches the fluorescence of the pendant fluorophores (see figure; PET=photo‐induced electron transfer). Anion binding to the boron center neutralizes

  十亿分之几的分量足以打开水溶液中的新型荧光氰化物传感器。由于其固有的电子缺陷，该传感器的阳离子硼部分不仅充当了高亲和力的阴离子结合位点，而且还淬灭了悬垂荧光团的荧光（见图； PET =光诱导的电子转移）。结合到硼中心的阴离子中和了硼烷单元的电子接受特性，从而恢复了悬垂荧光团的荧光。
• High-affinity fluorescent ligands for the 5-HT3 receptor
  作者：Jonathan Simonin、Sanjeev Kumar V. Vernekar、Andrew J. Thompson、J. Daniel Hothersall、Christopher N. Connolly、Sarah C.R. Lummis、Martin Lochner

  DOI：10.1016/j.bmcl.2011.11.097

  日期：2012.1

  The synthesis, photophysical and biological characterization of a small library of fluorescent 5-HT3 receptor ligands is described. Several of these novel granisetron conjugates have high quantum yields and show high affinity for the human 5-HT(3)AR. (C) 2011 Elsevier Ltd. All rights reserved.
• Zn2+ fluorescent chemosensors and the influence of their spacer length on tuning Zn2+ selectivityElectronic supplementary information (ESI) available: job plot, partial 1H NMR spectra of free 3 and the 3–Zn2+ complex, Ca2+ and Mg2+ interference for Zn2+ sensing of 3, Kd measurements, and buffer preparation. See http://www.rsc.org/suppdata/p2/b2/b200462c/
  作者：Tae Woo Kim、Jung-hyun Park、Jong-In Hong

  DOI：10.1039/b200462c

  日期：2002.4.29

  Zn2+ fluorescent chemosensors based on the chelation-enhanced fluorescence (CHEF) mechanism were prepared and fine-tuning of their Zn2+ selectivity was achieved by control of the spacer length. The fluorescence emission response to metal ions shows a fluorescence decrease for Co2+, Cu2+ and Ni2+ and an increase for Ca2+, Cd2+ and Zn2+. Maximum Zn2+ selectivity over Ca2+ and Cd2+ was achieved with 3. The basic binding properties (stoichiometry, apparent dissociation constant, and pH dependence) were measured by fluorescence spectroscopy. Analysis of the Job plot for the 3–Zn2+ complex indicates the formation of a 1 ∶1 complex. The apparent dissociation constant Kd was determined as 0.98 (±0.43) nM for 3–Zn2+ at pH 7.5 [50 mM HEPES buffer I = 0.1 (NaNO3)]. The plateaus in the fluorescence intensity of 2 and the 2–Zn2+ complex in regions with a pH exceeding 7 imply that the fluorescence measurements should be little affected by physiological pH changes.

  基于配位增强荧光（CHEF）机制的Zn2+荧光化学传感器被制备出来，并通过控制间隔基长度实现了对Zn2+选择性的精细调节。对金属离子的荧光发射响应显示，Co2+、Cu2+和Ni2+使荧光减弱，而Ca2+、Cd2+和Zn2+使荧光增强。在3号传感器中实现了对Zn2+的最大选择性，优于Ca2+和Cd2+。基本结合特性（化学计量比、表观解离常数和pH依赖性）通过荧光光谱法测量。3号传感器与Zn2+的Job图分析表明形成了1:1的复合物。表观解离常数Kd在pH 7.5时为0.98（±0.43）nM [50 mM HEPES缓冲液，I = 0.1 (NaNO3)]。在pH超过7的区域，2号传感器及其与Zn2+的复合物的荧光强度平稳，表明荧光测量受生理pH变化的影响不大。
• Synthesis and characterization of<i>N</i>-arylsulfonylazetidines
  作者：Songde Tan、Yiwen Chen、Ralph A. Zingaro、Joseph H. Reibenspies

  DOI：10.1002/jhet.5570450449

  日期：2008.7

  Abstractmagnified imageA convenient method for the synthesis of N‐arylsulfonyl azetidines using N‐(3‐bromopropyl)‐arylsulfonamide with cesium carbonate and potassium iodide in DMF is reported. The reaction conditions are optimized and seven N‐arylsulfonyl azetidines have been synthesized in good yield using this method. The structures of compounds 2a and 2e were determined by X‐ray crystallography.