methyl 3-(2-bromoethoxy)-naphthalene-2-carboxylate | 499137-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-(2-bromoethoxy)-naphthalene-2-carboxylate
• 英文别名: 2-Naphthalenecarboxylic acid, 3-(2-bromoethoxy)-, methyl ester；methyl 3-(2-bromoethoxy)naphthalene-2-carboxylate
• CAS: 499137-47-2
• 化学式: C₁₄H₁₃BrO₃
• mdl: MFCD12075254
• 分子量: 309.159
• InChiKey: LBIVFOMXUXEJIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-bromoethoxy)-naphthalene-2-carboxylate 在 lithium aluminium tetrahydride 、 氯化亚砜 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 24.0h， 生成 1,19-dichloro-2,3:17,18-dinaphthaleno-4,16-dioxa-7,10,13-trithianonadeca-2,17-diene
  参考文献：
  名称：

  A Convenient Synthesis of Novel 20-, 23-, and 26-Membered Macrocyclic Oxathiadibenzo- and Oxathiadinaphthalenocrown Ethers, Part 1

  摘要：

  一系列新型的氧硫杂环二苯并-和氧硫杂二萘冠醚1-18已经成功地以高产率和简单的方式合成。它们通过核磁共振、质谱和元素分析进行了表征。

  DOI：

  10.1515/znb-2005-0813
• 作为产物：
  描述：

  3-羟基-2-萘甲酸甲酯 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以83%的产率得到methyl 3-(2-bromoethoxy)-naphthalene-2-carboxylate
  参考文献：
  名称：

  A Convenient Synthesis of Novel 20-, 23-, and 26-Membered Macrocyclic Oxathiadibenzo- and Oxathiadinaphthalenocrown Ethers, Part 1

  摘要：

  一系列新型的氧硫杂环二苯并-和氧硫杂二萘冠醚1-18已经成功地以高产率和简单的方式合成。它们通过核磁共振、质谱和元素分析进行了表征。

  DOI：

  10.1515/znb-2005-0813

文献信息

• Facile synthesis and optical resolution of inherently chiral fluorescent calix[4]crowns: enantioselective recognition towards chiral leucinol
  作者：Jun Luo、Qi-Yu Zheng、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/j.tet.2005.06.015

  日期：2005.8

  series of tri-O-alkylated inherently chiral fluorescent calix[4]crowns in the cone conformations and a series of tetra-O-alkylated inherently chiral fluorescent calix[4]crowns in the partial cone conformations have been synthesized. By condensing with chiral auxiliary (S)-BINOL, the resulting diastereomers could be separated via preparative TLC. We found that the size of the crown moiety effected the separation

  合成了圆锥构象中的一系列三-O-烷基化的固有手性荧光杯[4]冠和一系列圆锥体构象中的一系列四-O-烷基化的固有手性荧光杯[4]冠。通过与手性助剂（S）-BINOL缩合，可以通过制备TLC分离得到的非对映异构体。我们发现冠部分的大小影响非对映异构体的分离。此外，通过水解除去BINOL单元提供了具有光学纯度的对映异构体对。此外，我们发现在部分锥构象6c中，四-O-烷基化的固有手性荧光杯[4] cro-6 对手性亮氨酸显示出相当高的对映选择性识别能力。
• A new fluorescent chemosensor for transition metal cations and on/off molecular switch controlled by pH
  作者：Yu-Dong Cao、Qi-Yu Zheng、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/s0040-4039(03)01074-8

  日期：2003.6

  A new fluorescent chemosensor with imidazole as ionophore was synthesized by the selective derivation of calixarene, which can effectively recognize Cu2+ and Zn2+ leading to different fluoroscopic behaviors in CH3OH–H2O. This system could be considered as a molecular switch. By modulating the pH of the solution, on–off–on fluorescent switching is carried out upon combinatory addition of acid, base

  通过杯芳烃的选择性衍生，合成了一种新的以咪唑为离子载体的荧光化学传感器，该传感器可以有效识别Cu 2+和Zn 2+，导致CH 3 OH-H 2 O中的荧光行为不同。转变。通过调节溶液的pH，在酸，碱和Cu 2+的组合添加中进行开-关-开荧光切换。
• Highly selective fluorescent sensing of Pb2+ by a new calix[4]arene derivative
  作者：Jun-Min Liu、Jian-Hua Bu、Qi-Yu Zheng、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/j.tetlet.2006.01.075

  日期：2006.3

  A new chemosensor was synthesized by the alkylation of p-tert-butyl-calix[4]arene with three N,N-diethylacetamide groups and one methyl 3-ethoxy-naphthalene-2-carboxylate, which exhibited highly selective fluorescent response to Pb2+ over alkali, alkali earth metal ions and some transition metal ions in CH3CN–H2O.

  一种新的化学传感器用的烷基化合成p -叔丁基杯[4]芳烃具有三个Ñ，Ñ -diethylacetamide基团和一个甲基3-乙氧基-萘-2-羧酸甲酯，其表现出高选择性的荧光响应的Pb 2 +在CH 3 CN–H 2 O中的碱金属，碱土金属离子和一些过渡金属离子上。
• A selective fluorescent probe for La3+ and Y3+ based on calix[6]arene
  作者：Jun-Min Liu、Chuan-Feng Chen、Qi-Yu Zheng、Zhi-Tang Huang

  DOI：10.1016/j.tetlet.2004.05.159

  日期：2004.7

  A new fluorescent probe based on calix[6]arene functionalized with three naphthoic acid groups was synthesized and showed selective fluorescence enhancement in the presence of La3+ and Y3+. In addition, the fluorescence enhancement behaviors depended on the pH values of the solution.

  合成了一种新的基于带有三个萘甲酸官能团的杯[6]芳烃的荧光探针，并在La 3+和Y 3+存在下显示出选择性的荧光增强作用。另外，荧光增强行为取决于溶液的pH值。
• A new fluorescent chemosensor for Fe3+ and Cu2+ based on calix[4]arene
  作者：Jun-Min Liu、Qi-Yu Zheng、Jun-Ling Yang、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/s0040-4039(02)02265-7

  日期：2002.12

  A novel fluorescent compound derived from calixarene which possesses two 3-alkoxy-2-naphthoic acid moieties has been synthesized in moderate yield. In H2O/CH3OH (1:1), its fluorescent intensity was quenched sharply in the presence of Cu2+ or Fe3+, and the degree of quenching was related to the pH of the solution. Other metal ions, such as Co2+, Ni2+, Zn2+, Mn2+, Mg2+ and Ba2+ did not affect its fluorescent spectra. This research may provide a new fluorescent probe for Cu2+ and Fe3+. (C) 2002 Elsevier Science Ltd. All rights reserved.