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benzyl 3,4,5-trimethoxybenzoate | 78277-28-8

中文名称
——
中文别名
——
英文名称
benzyl 3,4,5-trimethoxybenzoate
英文别名
Phenylmethyl 3,4,5-trimethoxybenzoate
benzyl 3,4,5-trimethoxybenzoate化学式
CAS
78277-28-8
化学式
C17H18O5
mdl
——
分子量
302.327
InChiKey
YFDWNFNMVLFDRW-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    61-62 °C
  • 沸点:
    393.8±12.0 °C(Predicted)
  • 密度:
    1.162±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.2
  • 重原子数:
    22
  • 可旋转键数:
    7
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.24
  • 拓扑面积:
    54
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    3,4,5-三甲氧基苯甲酰氯苯甲醇三乙胺 作用下, 以 乙腈 为溶剂, 反应 3.0h, 以75%的产率得到benzyl 3,4,5-trimethoxybenzoate
    参考文献:
    名称:
    Effect of natural and synthetic benzyl benzoates on calmodulin
    摘要:
    The present investigation describes the effect of the spasmolytic benzylbenzoates 1-9 from Brickellia veronicifolia on CaM using a functional in vitro enzymatic assay. Bovine brain PDE1 was used as a monitoring enzyme. The most active natural inhibitors of the system CaM-PDE1 were benzyl benzoates 3-5, which inhibited the activity of PDE1 in a concentration-dependent manner. In addition, three series of analogs of compound 4, compounds 10a-32a, were prepared and assayed. The benzyl benzoates from the first series, namely 10a-24a, possess no substituents on ring B but different number and position of hydroxyl or methoxy groups in ring A. The second group (25-32a), on the other hand, possesses an A ring identical to that on compound 4, but different substituents in Ring B. The most active compounds were 14a, 15a and 30a. These compounds were two to six times more potent than chlorpromazine, a well known CaM inhibitor. Benzyl benzoates 14a and 15a have methoxyl groups at C-2/C-4 and C-3/C-4 in ring A, respectively; while 30a, in addition to the methoxyl groups at C-2/C-6 of ring A, hold a benzoyloxy moiety at C-3' of ring B. Kinetic studies revealed that compounds 3, 4, 14a, 15a and 30a behave as competitive CaM antagonists. (c) 2007 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.phytochem.2007.02.026
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文献信息

  • Titanium superoxide – a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant
    作者:Soumen Dey、Sunita K. Gadakh、A. Sudalai
    DOI:10.1039/c5ob01586c
    日期:——

    A single step catalytic approach for the synthesis of esters from aldehydes using a recyclable heterogeneous catalyst is described.

    一种利用可回收的非均相催化剂从醛类合成酯的单步催化方法被描述。
  • Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues
    作者:Flávio R. Nóbrega、Larisse V. Silva、Carlos da Silva M. Bezerra Filho、Tamires C. Lima、Yunierkis P. Castillo、Daniel P. Bezerra、Tatjana K. Souza Lima、Damião P. de Sousa
    DOI:10.1155/2019/4785756
    日期:2019.1.8
    Most compounds were found to be active against L. amazonensis. Among 32 assayed derivatives, compound (E)-()-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity (IC50 = 0.007 ± 0.008 μM, SI > 10), followed by benzyl 3,4,5-trimethoxybenzoate (IC50 = 0.025 ± 0.009 μM, SI > 3.205) and (E)-furfuryl 3-(3,4,5-trimethoxyphenyl)-acrylate (IC50 = 0.029 ± 0.007 μM, SI > 2
    Piplartine 是一种存在于不同 Piper 物种中的烷酰胺,具有多种生物活性,包括抗寄生虫特性。因此,本研究的目的是评估一系列 32 种合成的 piplartine 类似物对抗 Leishmania amazonensis 前鞭毛体形式,并建立这些化合物的构效关系和 3D-QSAR。使用MTT方法确定化合物的抗利什曼病作用。大多数化合物被发现对 L. amazonensis 有活性。在 32 种测定的衍生物中,化合物 (E)-(-)-冰片基 3-(3,4,5-三甲氧基苯基)-丙烯酸酯表现出最有效的抗利什曼原虫活性(IC50 = 0.007 ± 0.008 μM,SI > 10),其次是苄基3,4,5-三甲氧基苯甲酸酯 (IC50 = 0.025 ± 0.009 μM, SI > 3.205) 和 (E)-糠基 3-(3,4,5-三甲氧基苯基)-丙烯酸酯 (IC50 = 0.029 ±
  • Palladium-Catalyzed Benzylation of Carboxylic Acids with Toluene via Benzylic C–H Activation
    作者:Hongqiang Liu、Guangfa Shi、Shulei Pan、Yuyu Jiang、Yanghui Zhang
    DOI:10.1021/ol401687f
    日期:2013.8.16
    Direct benzylation of carboxylic acids with toluene has been developed via palladium-catalyzed C-H acyloxylation under 1 atm of oxygen. This reaction demonstrates good functional group tolerance and high yields, providing a facile, atom-economic, and efficient method for the synthesis of benzyl esters.
  • An expedient esterification of aromatic carboxylic acids using sodium bromate and sodium hydrogen sulfite
    作者:Khalid Mohammed Khan、Ghulam Murtaza Maharvi、Safdar Hayat、Zia-Ullah、M. Iqbal Choudhary、Atta-ur-Rahman
    DOI:10.1016/s0040-4020(03)00812-3
    日期:2003.7
    Treatment of aromatic carboxylic acids and substituted toluenes with a mixture of sodium bromate and sodium hydrogen sulfite in a two-phase system gave the corresponding esters in good yield. The intermediate alpha-brominated toluene was formed by the in situ generated hypobromous acid. The alpha-bromotoluene underwent an intermolecular nucleophilic substitution reaction with aromatic carboxylic acids present in the reaction mixture to afford the corresponding esters. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • N-Heterocyclic Carbene-Mediated Oxidative Electrosynthesis of Esters in a Microflow Cell
    作者:Robert A. Green、Derek Pletcher、Stuart G. Leach、Richard C. D. Brown
    DOI:10.1021/acs.orglett.5b01459
    日期:2015.7.2
    An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes has been achieved in an undivided microfluidic electrolysis C-ell at ambient temperature. Productivities of up to 4.3 g h(-1) in a single pass are demonstrated, with excellent yields, and conversions for 19 examples presented: Notably, the oxidative acylation, reactions were,shown to proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols), with remarkably short residence tithes in the electrolysis cell (<13 s), and without added electrolyte.
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