methyl 3-decyloxybenzoate | 97067-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-decyloxybenzoate
• 英文别名: Methyl 3-(decyloxy)benzoate；methyl 3-decoxybenzoate
• CAS: 97067-80-6
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: YMRDFGZGYLPGPW-UHFFFAOYSA-N

物化性质

• 沸点：
  386.2±15.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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-decyloxybenzoate 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.08h， 生成 3-(decyloxy)-N-hydroxybenzamide
  参考文献：
  名称：

  Discovery of N-hydroxy-3-alkoxybenzamides as direct acid sphingomyelinase inhibitors using a ligand-based pharmacophore model

  摘要：

  Acid sphingomyelinase (ASM) has been shown to be involved in many physiological processes, emerging to be a promising drug target. In this study, we constructed a ligand-based pharmacophore model of ASM inhibitors and applied this model to optimize the lead compound alpha-mangostin, a known inhibitor of ASM. 23 compounds were designed and evaluated in vitro for ASM inhibition, of these, 10 compounds were found to be more potent than alpha-mangostin. This high hit ratio confirmed that the presented model is very effective and practical. The most potent hit, 1c, was found to selectively and competitively inhibit the enzyme and inhibit the generation of ceramide in a dose-dependent manner. Furthermore, 1c showed favorable anti-apoptosis and anti-inflammatory activity. Interactions with key residues and the Zn2+ cofactor of 1c were found by docking simulation. These results provide promising leads and important guidance for further development of efficient ASM inhibitors and drug candidates. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.065
• 作为产物：
  描述：

  癸基溴 、 3-羟基苯甲酸甲酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以74%的产率得到methyl 3-decyloxybenzoate
  参考文献：
  名称：

  取代模式和链长对烷氧基取代三苯基三唑并三嗪热致性质的影响

  摘要：

  通过 DSC、偏光光学显微镜 (POM) 和 X 射线散射制备并研究了具有三重烷氧基苯基取代的三三唑并三嗪 (TTT)。六个戊氧基链足以在这些星形化合物中诱导液晶行为。比较了具有不同取代模式和不同长度的线性链外围、链中分支和燕尾的 TTT 的热致性质。一般来说，这些盘显示出广泛且稳定的热致中间相，切向 TTT 优于径向异构体。研究了烷基链的数量、位置、长度和结构的构效关系。

  DOI：

  10.3390/molecules25235761

文献信息

• Discotic compounds for use in liquid crystal mixtures
  申请人：Secretary of State for Defence in her Britannic Majesty's Government of

  公开号：US05750050A1

  公开（公告）日：1998-05-12

  Liquid crystal compounds have been synthesized of general formula (I) and may be mixed with other liquid crystal compounds to give useful liquid crystal mixtures which may then be used in liquid crystal devices. Such devices include linear and non-linear electrical, optical and electro-optical devices, magneto-optical devices and devices providing responses to stimuli such as temperature changes and total or partial pressure changes. Formula (I) where each Z.sub.1-6 is given by formula (II), where Y for each of Z.sub.1-6 is independently COO, OCO, CH.sub.2 O and OCH.sub.2, m defines the number of substituents on each of Z.sub.1-6 and is independently 0-5,and X is independently for each substituent on each of Z.sub.1-6 alkyl (straight chain, branched and chiral), alkoxy (straight chain, branched or chiral), alkanoyl (straight chain, branched or chiral), alkenyl (straight chain, branched or chiral), halogen, halogenoalkyl (straight chain, branched or chiral) and CN, provided that at least one of Z.sub.-6 1 has at least one substituent X, and excluding where m is 1 for each of Z.sub.1-6, Y is COO for each of Z.sub.1-6 and X is n-alkyl or n-alkoxy positioned para to Y for each of Z.sub.1-6 and also where M is 5 for each of Z.sub.1-6, Y is COO for each of Z.sub.1-6 and for each Z.sub.1-6 X is selected as n-alkoxy positioned para to Y and fluoride for all other substituents.

  已经合成了一般式(I)的液晶化合物，可以与其他液晶化合物混合，形成有用的液晶混合物，然后可以在液晶设备中使用。这些设备包括线性和非线性电学、光学和电光学设备、磁光学设备以及对温度变化和总体或局部压力变化等刺激提供响应的设备。公式(I)中，每个Z.sub.1-6由公式(II)给出，其中Z.sub.1-6的每个Y独立地为COO、OCO、CH.sub.2O和OCH.sub.2，m定义Z.sub.1-6的每个取代基的数量，独立地为0-5，X独立地为Z.sub.1-6的每个取代基选择烷基(直链、支链和手性)、烷氧基(直链、支链或手性)、烷酰基(直链、支链或手性)、烯基(直链、支链或手性)、卤素、卤素烷基(直链、支链或手性)和CN，前提是至少有一个Z.sub.-6 1具有至少一个取代基X，但不包括当m为1时，Z.sub.1-6的每个Y均为COO，Z.sub.1-6的每个取代基X均为在Y的对位上的n-烷基或n-烷氧基，以及当M为5时，Z.sub.1-6的每个Y均为COO，对于每个Z.sub.1-6，X均选择在Y的对位上的n-烷氧基，所有其他取代基均选择氟代物。
• DISCOTIC COMPOUNDS FOR USE IN LIQUID CRYSTAL MIXTURES
  申请人：The Secretary of St. for Def. in her Britannic Maj. Governm of the Un. Kingdom of Gr. Brit. and N. Ireland

  公开号：EP0702668A1

  公开（公告）日：1996-03-27
• US4251545A
  申请人：——

  公开号：US4251545A

  公开（公告）日：1981-02-17
• US5750050A
  申请人：——

  公开号：US5750050A

  公开（公告）日：1998-05-12
• [EN] DISCOTIC COMPOUNDS FOR USE IN LIQUID CRYSTAL MIXTURES<br/>[FR] COMPOSES EN FORME DE DISQUE UTILISES DANS DES MELANGES POUR CRISTAUX LIQUIDES
  申请人：THE SECRETARY OF STATE FOR DEFENCE IN HER BRITANNIC MAJESTY'S GOVERNMENT OF THE UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND

  公开号：WO1994029263A1

  公开（公告）日：1994-12-22

  (EN) Novel liquid crystal compounds have been synthesised of general formula (I). These compounds may be mixed with other liquid crystal compounds to give useful liquid crystal mixtures which may then be used in liquid crystal devices. Such devices include linear and non-linear electrical, optical and electro-optical devices, magneto-optical devices and devices providing responses to stimuli such as temperature changes and total or partial pressure changes. Formula (I) where each of Z1-6 is given by formula (II), where Y for each of Z1-6 is independently selected from COO, OCO, CH2O, and OCH2, m defines the number of substituents on each of Z1-6 and is independently selected from 0-5, and X is independently selected for each substituent on each of Z1-6 from alkyl (straight chain, branched and chiral), alkoxy (straight chain, branched or chiral), alkanoyl (straight chain, branched or chiral), alkenyl (straight chain, branched or chiral), halogen, halogenoalkyl (straight chain, branched or chiral) and CN, provided that at least one of Z1-6 has at least one substituent X, and excluding where m is 1 for each of Z1-6, Y is COO for each of Z1-6 and X is $i(n)-alkyl or $i(n)-alkoxy positioned para to Y for each of Z1-6, and also where m is 5 for each of Z1-6, Y is COO for each of Z1-6 and for each Z1-6 X is selected as $i(n)-alkoxy positioned para to Y and fluoride for all other substituents.(FR) On décrit des composés de cristaux liquides synthétisés de formule générale (I). Ces composés peuvent être mélangés à d'autres composés de cristaux liquides pour donner des mélanges utiles pouvant ainsi à leur tour être employés dans des dispositifs à cristaux liquides. De tels dispositifs comprennent des dispositifs électriques, optiques et électro-optiques linéaires et non linéaires, des dispositifs magnéto-optiques et des dispositifs fournissant des réponses à des stimuli tels que des variations de température et des variations de pression totale ou partielle. Formule (I) dans laquelle chaque composant Z1-6 est donné par la formule (II) dans laquelle Y est choisi indépendamment parmi COO, OCO, CH2O et OCH2; m représente le nombre de substituants sur chaque Z1-6 et vaut indépendamment de 0 à 5 et X est indépendamment choisi pour chaque substituant sur chaque Z1-6 parmi alkyle (chaîne droite, chaîne ramifiée et chaîne chirale), alkoxy (chaîne droite, ramifiée ou chirale), alkanoyle (chaîne droite, ramifiée ou chirale), alkényle (chaîne droite, ramifiée ou chirale), halogène, halogéno-alkyle (chaîne droite, ramifiée ou chirale) et CN, à condition qu'au moins l'un des Z1-6 possède au moins un substituant X et que les valeurs suivantes sont exclues: m=1 pour chaque Z1-6, Y représente COO pour chaque Z1-6 et X représente alkyle ou alcoxy en position para par rapport à Y pour chaque Z1-6 et aussi lorsque m=5 pour chaque Z1-6, Y représente COO pour chaque Z1-6 et pour chaque Z1-6 est choisi comme alcoxy en position para par rapport à Y et comme fluorure pour tous les autres substituants.