3-(naphthalene-1-yloxy)propyl methanesulfonate | 724461-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalene-1-yloxy)propyl methanesulfonate
• 英文别名: 3-(naphthalen-1-yloxy)propyl methanesulfonate；3-Naphthalen-1-yloxypropyl methanesulfonate；3-naphthalen-1-yloxypropyl methanesulfonate
• CAS: 724461-84-1
• 化学式: C₁₄H₁₆O₄S
• 分子量: 280.345
• InChiKey: DCIADTXEDWOXBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  3-(naphthalene-1-yloxy)propyl methanesulfonate 在 1-丁基-3-甲基咪唑溴盐 作用下， 反应 1.0h， 以99%的产率得到1-(3-溴丙氧基)萘
  参考文献：
  名称：

  可回收离子液体 [bmim][X] 磺酸酯亲核取代反应的简便绿色方案

  摘要：

  离子液体 [bmim][X] (X = Cl, Br, I, OAc, SCN) 是用于伯醇和仲醇衍生的磺酸酯亲核取代反应的高效试剂。离子液体的抗衡阴离子 (X-) [bmim][X] 有效地替代了磺酸盐，以优异的产率提供了相应的取代产物，如烷基卤化物、乙酸盐和硫氰化物。新开发的协议对环境非常有吸引力，因为在大多数情况下，反应使用化学计量的离子液体作为唯一试剂，不需要额外的溶剂、任何其他活化试剂、非常规设备或特殊预防措施。此外，这些离子液体可以很容易地回收利用而不会损失反应性，从而使整个过程“更环保”。

  DOI：

  10.1055/s-0032-1317473
• 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 5.08h， 生成 3-(naphthalene-1-yloxy)propyl methanesulfonate
  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

• NOVEL ANTICANCER AGENT
  申请人：KTN BioTec, Inc.

  公开号：US20150353473A1

  公开（公告）日：2015-12-10

  The present invention aims to provide a compound having an anticancer action comparable or superior to that of naftopidil. A compound represented by the formula (I) wherein each symbol is as defined in the SPECIFICATION, or a pharmaceutically acceptable salt thereof, particularly 1-((2-((2-methoxyphenyl)amino)ethyl)amino)-3-(1-naphthyloxy)propan-2-ol, or a pharmaceutically acceptable salt thereof. The compound shows a cell proliferation suppressive action on a wide range of cancer cells, is useful as an anti-cancer agent, and is useful for the prophylaxis and/or treatment of cancer.

  本发明旨在提供一种具有与萘哌地尔相当或更优的抗癌作用的化合物。该化合物由式(I)表示，其中每个符号的定义如说明书中所述，或其药学上可接受的盐，特别是1-((2-((2-甲氧基苯基)氨基)乙基)氨基)-3-(1-萘氧基)丙烷-2-醇，或其药学上可接受的盐。该化合物对广泛的癌细胞显示出细胞增殖抑制作用，可用作抗癌剂，并可用于癌症的预防和/或治疗。
• Catalytic nucleophilic fluorination by an imidazolium ionic liquid possessing trialkylphosphine oxide functionality
  作者：Minakshmi Paramanik、Rekha Singh、Sulekha Mukhopadhyay、Sunil K. Ghosh

  DOI：10.1016/j.jfluchem.2015.06.022

  日期：2015.10

  The synthesis of a new alkylmethylimidazolium ionic liquid wherein the alkyl group is functionalized with dihexylphosphine oxide moiety at the terminal position has been achieved in four steps from 1-methylimidazole. This hybrid ionic liquid effectively catalyzed the nucleophilic fluorination of primary alkyl mesylates under mild conditions using CsF as the fluoride source with a faster rate compared

  从1-甲基咪唑通过四个步骤已经完成了新的烷基甲基咪唑鎓离子液体的合成，其中烷基在末端位置被二己基膦氧化物部分官能化。与丁基甲基咪唑鎓甲磺酸盐相比，该杂化离子液体在温和条件下使用CsF作为氟化物源，可有效催化伯烷基甲磺酸酯的亲核氟化反应。将杂化催化剂再循环5次，而不会损害产物的产率和纯度。的亲核氟化已经用于二的合成2-（5-氟戊基）-2-甲基丙二酸二乙酯，的前体18的细胞凋亡显像剂F的同位素和保护形式ø - （2'-氟乙基） -升-酪氨酸肿瘤显像剂的18 F同位素。
• Facile calculation of specific rate constants and activation energies of 18F-fluorination reaction using combined processes of coat-capture–elution and microfluidics
  作者：Bo Yeun Yang、Jae Min Jeong、Yun-Sang Lee、Dong Soo Lee、June-Key Chung、Myung Chul Lee

  DOI：10.1016/j.tet.2011.01.088

  日期：2011.4

  Calculation of a specific rate constant (k) and activation energy (Ea) of 18F-labeling reaction is important to obtain objective data. However, it has never been tried, because short time heating required for the calculation of the parameters was difficult. In the present study, we could calculate the parameters using combination of coat-capture–elution method (Aerts et al.) and microfluidic processes

  18 F标记反应的比速率常数（k）和活化能（E a）的计算对于获得客观数据很重要。但是，从未尝试过，因为难以快速计算参数所需的加热时间。在本研究中，我们可以结合使用外套捕获-洗脱方法（Aerts等人）和微流体过程来计算参数。在丙酮，MeCN和t- BuOH中获得的Ts-萘酚的E a值分别为5.83、8.98和13.54 kcal / mol，在相同溶剂中获得的Ms-萘酚的E a值分别为5.81、8.16和19.34 kcal / mol，分别。这些参数的计算对于设置[18 F]氟化程序，用于开发新的前体。
• JP6041303
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] COMPOUND LIBRARIES OF 2, 3, 4, 9-TETRAHYDROSPIRO (BETA-CARBOLINE-1, 4 -PIPERIDINE) DERIVATIVES AND RELATED COMPOUNDS FOR TARGETTING COMPOUNDS CAPABLE OF BINDING TO THE G-PROTEIN RECEPTOR<br/>[FR] BANQUES DE DERIVES DE 2, 3, 4, 9-TETRAHYDROSPIRO(BETA-CARBOLINE-1,4-PIPERIDINE) ET DE COMPOSES APPARENTES SERVANT A CIBLER DES COMPOSES CAPABLES DE SE FIXER AU RECEPTEUR DE LA PROTEINE G
  申请人：BIOFOCUS PLC

  公开号：WO2004058263A1

  公开（公告）日：2004-07-15

  The present invention provides a compound library designed to target the interplay of electron-rich rings and basic amines. The spatial arrangements between these functions can be captured in two ways, one is captured in series of spiro-fused piperidines which show a propensity to interact with all-helical environments, and the other is present in a more folded back isoquinoline type arrangement. In GPCRs the basic function is commonly found to interact with TM3 aspartates and the electron-rich ring often is stabilised by Phe or Tyr and Ser or Thr on TM4 and TM5. The library is also designed to extend this recognition site for a subset of compounds to recruit antagonist recognition sites around TM7. The library comprises or consists of a set of structurally related compounds of general formulae A, B and C.