ethyl 3,5-dimethyl-4-hydroxybenzoate | 61660-77-3

• 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: ethyl 3,5-dimethyl-4-hydroxybenzoate
• 英文别名: ethyl 4-hydroxy-3,5-dimethylbenzoate
• CAS: 61660-77-3
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD01762589
• 分子量: 194.23
• InChiKey: GWPIVLOGQNMUAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  112-116 °C
• 沸点：
  314.1±37.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3,5-dimethyl-4-hydroxybenzoate 在 chromium(VI) oxide 、 硫酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 41.0h， 生成 3,5-diformyl-4-hydroxybenzoic acid ethyl ester
  参考文献：
  名称：

  Discovery of Novel Small Molecule Inhibitors of Dengue Viral NS2B-NS3 Protease Using Virtual Screening and Scaffold Hopping

  摘要：

  By virtual screening, compound 1 was found to be active against NS2B-NS3 protease (IC50 = 13.12 +/- 1.03 mu M). Fourteen derivatives (22) of compound 1 were synthesized, leading to the discovery of four new inhibitors with biological activity. In order to expand the chemical diversity of the inhibitors, small-molecule-based scaffold hopping was performed on the basis of the common scaffold of compounds 1 and 22. Twenty-one new compounds (23, 24) containing quinoline (new scaffold) were designed and synthesized. Protease inhibition assays revealed that 12 compounds with the new scaffold are inhibitors of NS2B-NS3 protease. Taken together, 17 new compounds were discovered as NS2B-NS3 protease inhibitors with IC50 values of 7.46 +/- 1.15 to 48.59 +/- 3.46 mu M, and 8 compounds belonging to two different scaffolds are active to some extent against DENY based on luciferase reporter replicon-based assays. These novel chemical entities could serve as lead structures for discovering therapies against DENY.

  DOI：

  10.1021/jm300146f
• 作为产物：
  描述：

  4-羟基-3,5-二甲基苯甲酸 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 ethyl 3,5-dimethyl-4-hydroxybenzoate
  参考文献：
  名称：

  Tetralin esters of phenols or benzoic acids having retinoid like activity

  摘要：

  该公式中化合物展现出类似视黄醇的活性，其中R基可以独立地是氢或较低烷基；A是--C(O)O--，--OC(O)--，--C(O)S--或--SC(O)--；n为0-5；Z是H，--COB，其中B为--OH或药用可接受的盐，或者B为--OR.sub.1，其中R.sub.1是酯形成基团，或者B为--N(R).sub.2，其中R为氢或较低烷基，或Z为--OE，其中E为氢或醚形成基团，或--COR.sub.2，其中R.sub.2为氢、较低烷基、苯基或较低烷基苯基，或者Z为--CHO或其缩醛衍生物，或者Z为--COR.sub.3，其中R.sub.3为--(CH.sub.2).sub.m CH.sub.3，其中m为0-4，且n和m的总和不超过4。

  公开号：

  US05130335A1

文献信息

• Pharmaceutical compositions comprising a basic drug compound, a surfactant, and a physiologically tolerable water soluble acid
  申请人：Vandecruys Roger Petrus Gerebern

  公开号：US09192577B2

  公开（公告）日：2015-11-24

  The invention provides a novel pharmaceutical composition comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base characterized in that the acid respectively base:drug compound ratio is at least 1:1 by weight.

  这项发明提供了一种新型的药物组合物，包括一种碱性或酸性药物化合物、表面活性剂和一种生理耐受的水溶性酸或碱，其特点在于酸或碱与药物化合物的比例至少为1:1（按重量计）。
• Isomorphous Crystals by Chloro–Methyl Exchange in Polymorphic Fuchsones
  作者：Naba K. Nath、Ashwini Nangia

  DOI：10.1021/cg3010097

  日期：2012.11.7

  The X-ray crystal structures of four fuchsone derivatives in which a chloro group is replaced by methyl were analyzed to understand isostructurality upon Cl–Me exchange in a polymorphic family of molecules. The four methyl groups in tetramethyl fuchsone (TMF, 2,6-dimethyl and α,α-di-p-tolyl) were substituted with chlorine pairwise to give dichloro dimethyl (CMF, 2,6-dichloro and α,α-di-p-tolyl), dimethyl

  分析了四种紫杉醇衍生物的X射线晶体结构，其中氯基被甲基取代，以了解在多态分子家族中进行Cl-Me交换时的同构性。将四甲基紫杉酮中的四个甲基（TMF，2,6-二甲基和α，α-二-对甲苯基）成对地取代成氯，得到二氯二甲基（CMF，2,6-二氯和α，α-二-对-甲苯基）对甲苯基），二甲基二氯（MCF，2,6-二甲基和α，α-二-对氯苯基）和四氯衍生物（TCF，2,6-二氯和α，α-二-对苯基）-氯苯基）。前三种化合物是多晶型的，而TCF仅提供一种晶体修饰。TMF，CMF和MCF是同构晶体和同构晶体，属于多晶型物，固溶体和溶剂化物。据报道，紫红色染料中颜色多态性的第一种情况是CMF双晶型。固溶体的形成是最严格的同构性测试之一，对TMF，CMF和MCF观察到，但对TCF观察不到。TCF中的晶体堆积以短的Cl··Cl相互作用为主，因此该晶体结构与前三个成员不同，这在很大程度上是空间填充的结果。使用XP
• Introducing a Cantellation Strategy for the Design of Mesoporous Zeolite-like Metal–Organic Frameworks: Zr-sod-ZMOFs as a Case Study
  作者：Norah Alsadun、Georges Mouchaham、Vincent Guillerm、Justyna Czaban-Jóźwiak、Aleksander Shkurenko、Hao Jiang、Prashant M. Bhatt、Prakash Parvatkar、Mohamed Eddaoudi

  DOI：10.1021/jacs.0c10007

  日期：2020.12.9

  mesoporous zirconium-based metal-organic frameworks (MOFs) with zeolitic sodalite (sod) topology. Zr-sod-ZMOF-1 and -2 are constructed based on a novel cantellation design strategy. Distinctly, organic linkers are judiciously designed in order to promote the deployment of the 12-coordinated Zr hexanuclear molecular building block (MBB) as a tetrahedral secondary building unit, a prerequisite for zeolite-like

  在此，我们报告了具有沸石方钠石 (sod) 拓扑结构的新型介孔锆基金属有机框架 (MOF)。Zr-sod-ZMOF-1 和 -2 是基于新颖的cantellation 设计策略构建的。显然，有机连接器的设计是明智的，以促进 12 配位的 Zr 六核分子结构单元 (MBB) 作为四面体二级结构单元的部署，这是类沸石网的先决条件。所得的 Zr-sod-ZMOFs 表现出直径高达 ≈43 Å 的中孔，而 Zr-sod-ZMOF-1 的孔体积为 1.98 cm3·g-1，是基于沸石类 MOFs 的最高报告实验值在 MBB 上作为四面体节点。
• [EN] HIV INHIBITING PYRIMIDINES DERIVATIVES<br/>[FR] DERIVES DE PYRIMIDINES INHIBITEURS DE VIH
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2003016306A1

  公开（公告）日：2003-02-27

  This invention concerns HIV replication inhibitors of formula (I) the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof, wherein the ring containing -a?1=a2-a3=a4¿- and -b?1=b2-b3=b4¿- represents phenyl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl;n is 0 to 5; m is 1 to 4; R1 is hydrogen; aryl; formyl; C¿1-6?alkylcarbonyl; C?1-6¿alkyl; C¿1-6?alkyloxycarbonyl, substituted C1-6alkyl, C1-6alkylcarbonyl; R?2¿ is hydroxy, halo, optionally substituted C¿1-6?alkyl, C3-7cycloalkyl, optionally substituted C2-6alkenyl, optionally substituted C2-6alkynyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, -S(=O)pR?6¿, -NH-S(=O)¿pR?6, -C(=O)R6, -NHC(=O)H, -C(=O)NHNH?2?, -NHC(=O)R?6¿, -C(=NH)R6 or a 5-membered heterocycle; X¿1? is -NR?5¿-, -NH-NH-, -N=N-, -O-, -C(=O)-, C¿1-4?alkanediyl, -CHOH-, -S-, -S(=O)p-, -X2-C1-4alkanediyl- or -C1-4alkanediyl-X2-; R?3 is NHR13; NR13R14¿; -C(=O)-NHR13; -C(=O)-NR13R14; -C(=O)-R15; -CH=N-NH-C(=O)-R16; substituted C¿1-6?alkyl; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl; substituted C2-6alkynyl; C1-6alkyl substituted with hydroxy and a second substituent; -C(=N-O-R?8)-C¿1-4alkyl; R7; or -X¿3?-R?7; R4¿ is halo, hydroxy, C¿1-6?alkyl, C3-7cycloalkyl, C1-6alkyloxy, cyano, nitro, polyhaloC1-6alkyl, polyhaloC1-6alkyloxy, aminocarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyl, formyl, amino, mono- or di(C1-4alkyl)amino; their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them.

  本发明涉及公式（I）的HIV复制抑制剂，其N-氧化物，药学上可接受的加成盐，季铵盐和立体化学异构体形式，其中含有-a?1=a2-a3=a4¿-和-b?1=b2-b3=b4¿-的环表示苯基，吡啶基，嘧啶基，吡嗪基，吡啶嗪基; n为0至5; m为1至4; R1为氢; 芳基; 甲酰基; C¿1-6?烷基酰基; C?1-6¿烷基; C¿1-6?烷氧羰基，取代的C1-6烷基，C1-6烷基酰基; R?2¿为羟基，卤素，可选取代的C¿1-6?烷基，C3-7环烷基，可选取代的C2-6烯基，可选取代的C2-6炔基，C1-6烷氧基，C1-6烷氧羰基，羧基，氰基，硝基，氨基，单烷基或二（C1-6烷基）氨基，多卤代甲基，多卤代甲氧基，多卤代甲硫基，-S（= O）pR?6¿，-NH-S（= O）¿pR?6，-C（= O）R6，-NHC（= O）H，-C（= O）NHNH?2？，-NHC（= O）R?6¿，-C（= NH）R6或5-成员杂环; X¿1？为-NR?5¿-，-NH-NH-，-N=N-，-O-，-C（= O）-，C¿1-4?烷二基，-CHOH-，-S-，-S（= O）p-，-X2-C1-4烷二基-或-C1-4烷二基-X2-; R?3为NHR13; NR13R14¿; -C（= O）-NHR13; -C（= O）-NR13R14; -C（= O）-R15; -CH=N-NH-C（= O）-R16; 取代的C¿1-6?烷基; 可选取代的C1-6烷氧C1-6烷基; 取代的C2-6烯基; 取代的C2-6炔基; C1-6烷基取代羟基和第二取代基; -C（= N-O-R?8）-C¿1-4烷基; R7; 或-X¿3？-R?7; R4¿为卤素，羟基，C¿1-6?烷基，C3-7环烷基，C1-6烷氧基，氰基，硝基，多卤代C1-6烷基，多卤代C1-6烷氧基，氨基羰基，C1-6烷氧羰基，C1-6烷基羰基，甲酰基，氨基，单烷基或二（C1-4烷基）氨基; 它们作为药物的用途，其制备过程和包含它们的制药组合物。
• Hiv inhibiting pyrimidines derivatives
  申请人：——

  公开号：US20040198739A1

  公开（公告）日：2004-10-07

  This invention concerns HIV replication inhibitors of formula (I) the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof, wherein the ring containing -a 1 =a 2 -a 3 =a 4 - and -b 1 =b 2 -b 3 =b 4 - represents pheynl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl;n is 0 to 5; m is 1 to 4; R 1 is hydrogen; aryl; formyl; C 1-6 alkylcarbonyl; C 1-6 alkyl; C 1-6 alkyloxycarbonyl, substituted C 1-6 alkyl, C 1-6 alkylcarbonyl; R 2 is hydroxy, halo, optionally substituted C 1-6 alkyl, C 3-7 cycloalkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, C 1-6 alkyloxy, C 1-6 alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C 1-6 alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, —S(═O) p R 6 , —NH—S(═O) p R 6 , —C(═O)R 6 , —NHC(═O)H, —C(═O)NHNH?2?, —NHC(═O)R 6 , —C(═NH)R 6 or a 5-membered hetrocycl; X 1 is —NR 5 —, —NH—NH—, —N═N—, —O—, —C(═O)—, C 1-4 alkanediyl, —CHOH—, —S—, —S(═O) p —, —X 2 —C 1-4 alkanediyl- or —C 1-4 alkanediyl-X 2 —; R 3 is NHR 13 , NR 13 R 14 ; —C(═O)—NHR 13 ; —C(═O)—NR 13 R 14 ; —C(═O)—R 15 ; —CH═N—NH—C(═O)—R 16 ; substituted C 1-6 alkyl; optionally substituted C 1-6 alkyloxyC 1-6 alkyl; substituted C 2-6 alkenyl; substituted C 2-6 alkynyl; substituted C 2-6 alkylenyl; C 1-6 alkyl substituted with hydroxy and a second substituent; —C(═N—O—R 8 )—C 1-4 alkyl; R 7 ; or —X 3 —R 7 ; R 4 is halo, hydroxy, C 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkyloxy, cyano, nitro, polyhaloC 1-6 alkyl, polyhaloC 1-6 alkyloxy, aminocarbonyl, C 1-6 alkyloxycarbonyl, C 1-6 alkylcarbonyl, formyl, amino, mono- or di(C 1-4 alkyl) amino; their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them. 1

  本发明涉及公式（I）的HIV复制抑制剂，其N-氧化物，药学上可接受的加成盐，季铵盐及其立体化学异构体，其中包含-a1＝a2-a3＝a4-和-b1＝b2-b3＝b4-的环表示苯基，吡啶基，嘧啶基，吡嗪基，吡咯嗪基；n为0至5；m为1至4；R1为氢；芳基；甲酰基；C1-6烷基羰基；C1-6烷基；C1-6烷氧羰基，取代的C1-6烷基，C1-6烷基羰基；R2为羟基，卤素，可选取代的C1-6烷基，C3-7环烷基，可选取代的C2-6烯基，可选取代的C2-6炔基，C1-6烷氧基，C1-6烷氧羰基，羧基，氰基，硝基，氨基，单烷基或双（C1-6烷基）氨基，多卤甲基，多卤甲氧基，多卤甲硫基，-S(═O)pR6，-NH-S(═O)pR6，-C(═O)R6，-NHC(═O)H，-C(═O)NHNH?2?，-NHC(═O)R6，-C(═NH)R6或5-成员杂环；X1为-NR5-，-NH-NH-，-N═N-，-O-，-C(═O)-，C1-4烷二基，-CHOH-，-S-，-S(═O)p-，-X2-C1-4烷二基-或-C1-4烷二基-X2-；R3为NHR13，NR13R14；-C(═O)-NHR13；-C(═O)-NR13R14；-C(═O)-R15；-CH═N-NH-C(═O)-R16；取代的C1-6烷基；可选取代的C1-6烷氧基C1-6烷基；取代的C2-6烯基；取代的C2-6炔基；取代的C2-6烷基；C1-6烷基取代羟基和第二取代基；-C(═N-O-R8)-C1-4烷基；R7；或-X3-R7；R4为卤素，羟基，C1-6烷基，C3-7环烷基，C1-6烷氧基，氰基，硝基，多卤C1-6烷基，多卤C1-6烷氧基，氨基羰基，C1-6烷氧羰基，C1-6烷基羰基，甲酰基，氨基，单烷基或双（C1-4烷基）氨基；它们作为药物的用途，它们的制备方法和包含它们的制药组合物。