2-(naphthalene-1-yloxy)ethylmethanesulfonate | 63649-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalene-1-yloxy)ethylmethanesulfonate
• 英文别名: 2-(1-naphthyloxy)ethanol O-methanesulfonate；2-naphthalen-1-yloxyethyl methanesulfonate
• CAS: 63649-90-1
• 化学式: C₁₃H₁₄O₄S
• 分子量: 266.318
• InChiKey: QRXLRRPTCPKNCC-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±28.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(naphthalene-1-yloxy)ethylmethanesulfonate 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 N,N-dimethyl-3-(3-(3-((naphthalene-1-yloxy)ethoxy)prop-1-yn-1-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine
  参考文献：
  名称：

  Synthesis and inhibitory evaluation of 3-linked imipramines for the exploration of the S2 site of the human serotonin transporter

  摘要：

  The human serotonin transporter is the primary target of several antidepressant drugs, and the importance of a primary, high affinity binding site (S1) for antidepressant binding is well documented. The existence of a lower affinity, secondary binding site (S2) has, however, been debated. Herein we report the synthesis of 3-position coupled imipramine ligands from clomipramine using a copper free Sonogashira reaction. Ligand design was inspired by results from docking and steered molecular dynamics simulations, and the ligands were utilized in a structure-activity relationship study of the positional relationship between the S1 and S2 sites. The computer simulations suggested that the S2 site does indeed exist although with lower affinity for imipramine than observed within the S1 site. Additionally, it was possible to dock the 3-linked imipramine analogs into positions which occupy the S1 and the S2 site simultaneously. The structure activity relationship study showed that the shortest ligands were the most potent, and mutations enlarging the proposed S2 site were found to affect the larger ligands positively, while the smaller ligands were mostly unaffected. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.039
• 作为产物：
  描述：

  萘酚 在 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 2-(naphthalene-1-yloxy)ethylmethanesulfonate
  参考文献：
  名称：

  Synthesis and inhibitory evaluation of 3-linked imipramines for the exploration of the S2 site of the human serotonin transporter

  摘要：

  The human serotonin transporter is the primary target of several antidepressant drugs, and the importance of a primary, high affinity binding site (S1) for antidepressant binding is well documented. The existence of a lower affinity, secondary binding site (S2) has, however, been debated. Herein we report the synthesis of 3-position coupled imipramine ligands from clomipramine using a copper free Sonogashira reaction. Ligand design was inspired by results from docking and steered molecular dynamics simulations, and the ligands were utilized in a structure-activity relationship study of the positional relationship between the S1 and S2 sites. The computer simulations suggested that the S2 site does indeed exist although with lower affinity for imipramine than observed within the S1 site. Additionally, it was possible to dock the 3-linked imipramine analogs into positions which occupy the S1 and the S2 site simultaneously. The structure activity relationship study showed that the shortest ligands were the most potent, and mutations enlarging the proposed S2 site were found to affect the larger ligands positively, while the smaller ligands were mostly unaffected. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.039

文献信息

• Method of treating lipidemia with aryloxyalkylaminobenzoic acids and
  申请人：American Cyanamid Company

  公开号：US04182776A1

  公开（公告）日：1980-01-08

  Aryloxyalkylaminobenzoic acids and esters as hypolipemic compounds.

  芳氧烷基氨基苯甲酸和酯作为降脂化合物。
• Naphthyloxyalkylaminobenzoic acids, salts and esters thereof
  申请人：American Cyanamid Company

  公开号：US04260816A1

  公开（公告）日：1981-04-07

  This disclosure describes pharmaceutical compositions having hypolipidemic and/or hypoglycemic activity which contain a substituted naphthyloxyalkylaminobenzoic acid or salt or ester thereof.

  这份披露描述了具有降脂和/或降糖活性的药物组合物，其中包含一种取代的萘氧烷基氨基苯甲酸或其盐或酯。
• One-Pot Approach for the Synthesis of Bis-indole-1,4-disubstituted-1,2,3-triazoles
  作者：Natthiya Saehlim、Teerapich Kasemsuk、Uthaiwan Sirion、Rungnapha Saeeng

  DOI：10.1021/acs.joc.8b02056

  日期：2018.11.2

  A new strategy for the synthesis of bis-indoletriazoles was developed using a sequential one-pot four-step procedure via I2 and H2SO4–SiO2 catalyzed Friedel–Crafts reactions of indole with aldehyde followed by N-alkylation with propargyl bromide, azidation, and copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). The reaction proceeded smoothly at room temperature in a short time, and a series of

  通过I 2和H 2 SO 4 -SiO 2催化的吲哚与醛的Friedel-Crafts反应，然后与炔丙基溴进行N-烷基化的连续一锅四步方法，开发了一种合成双吲哚三唑的新策略。，叠氮化和铜（I）催化的叠氮化物炔烃环加成（CuAAC）。反应在室温下在短时间内顺利进行，获得了一系列双吲哚三唑，收率良好至极好，证明了这种一锅法的普遍性。