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3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone | 34185-71-2

中文名称
——
中文别名
——
英文名称
3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone
英文别名
trans-2-methyl-3-(5′-carboxy-3′-methylpent-2′-enyl)-1,4-naphthoquinone;(4E)-6-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yl)-4-methylhex-4-enoic acid;trans-2-Methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-naphthoquinone;(E)-4-methyl-6-(3-methyl-1,4-dioxonaphthalen-2-yl)hex-4-enoic acid
3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone化学式
CAS
34185-71-2
化学式
C18H18O4
mdl
——
分子量
298.339
InChiKey
BCNIZSHMXASUGF-YRNVUSSQSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    3.2
  • 重原子数:
    22
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.28
  • 拓扑面积:
    71.4
  • 氢给体数:
    1
  • 氢受体数:
    4

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

  • 作为反应物:
    描述:
    3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone泼尼松龙 生成 [(E)-4-methyl-6-(3-methyl-1,4-dioxonaphthalen-2-yl)hex-4-enoyl] (8S,9S,10R,11R,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
    参考文献:
    名称:
    MORIMOTO, XIROSI;IMADA, ISUKEH;VATANABEH, MASAESI;MATSUMOTO, TAKEHO;OTSU,+
    摘要:
    DOI:
  • 作为产物:
    描述:
    参考文献:
    名称:
    ANTICOAGULANT COMPOUNDS AND THEIR USE
    摘要:
    根据该发明提供了一个化合物,其化学式为(I):其中R1、R2、R3和n的含义如描述中所示,或其药用可接受的溶剂化合物、盐或前药,用作抗凝剂。
    公开号:
    US20180092863A1
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文献信息

  • Ubiquinone and related compounds. XXXI. Synthesis of urinary metabolites of ubiquinone, phylloquinone, .ALPHA.-tocopherol and their related compounds.
    作者:MASAZUMI WATANABE、KAYOKO OKAMOTO、ISUKE IMADA、HIROSHI MORIMOTO
    DOI:10.1248/cpb.26.774
    日期:——
    Metabolites (XVIIa, b, c) of ubiquinone, phylloquinone and α-tocopherol, and their 2', 3'-dihydro (XXa, b, c), dicarboxy (XVIa, b, XXIIIa, b, c, XXIVa, b and XXVa, b) and 3'-demethyl (XXIa, b) derivatives were synthesized. During the synthetic studies of these compounds, we found that cis-4-acetoxy-1-bromo-2-methyl-2-butene (cis-III) was more reactive to nucleophiles than the corresponding trans isomer. γ-Vinyl-γ-butyrolactone (XII), which was a useful starting material for the synthesis of XXIa, b, was synthesized in one step from 1, 3-butadiene. The 3'-methyl group of XVIIa, b was not essential for the membrane-stabilizing activity in the rat-liver lysosome. Introduction of a carboxyl but not a carboxyl ester group into XVIIa, b resulted in a loss of the stabilizing activity.
    合成了泛醌、叶醌和α-生育酚的代谢物(XVIIa, b, c)及其2', 3'-二氢(XXa, b, c)、二羧基(XVIa, b, XXIIIa, b, c, XXIVa, b 和 XXVa, b)和3'-去甲基(XXIa, b)衍生物。在这些化合物的合成研究过程中,我们发现顺-4-乙氧基-1-溴-2-甲基-2-丁烯(cis-III)对核苷酸反应性比相应的反异构体更强。γ-乙烯基-γ-丁内酯(XII)作为合成XXIa, b的有用起始材料,可以一步从1, 3-丁二烯合成。XVIIa, b的3'-甲基基团对大鼠肝脏溶酶体的膜稳定活性并不是必需的。将羧基引入XVIIa, b,而不是羧酸酯基团,会导致稳定活性的丧失。
  • Ubiquinone and Related Compounds. XXVII. Synthesis of Urinary Metabolites of Phylloquinone and α-Tocopherol
    作者:MASAZUMI WATANABE、MITSURU KAWADA、MASAO NISHIKAWA、ISUKE IMADA、HIROSHI MORIMOTO
    DOI:10.1248/cpb.22.566
    日期:——
    The syntheses of the metabolites of phylloquinone, α-tocopherol and ubiquinones are described. 1. 2, 3, 5-Trimethyl-6-(3'-carboxybutyl)-1, 4-benzoquinone (VIIa), 2-methyl-3-(3'-carboxybutyl)-1, 4-naphthoquinone (VIIb) and 2, 3-dimethoxy-5-methyl-6-(3'-carboxybutyl)-1, 4-benzoquinone (VIIc) were synthesized by two routes. 2, 3, 5-Trimethylphenol (Ia) and 3-methyl-1-naphthol (Ib) were condensed with methylsuccinic anhydride (II), followed by reduction of the carbonyl groups and oxidation of the phenols to quinones (VIIa, VIIb). 2, 3, 5-Trimethyl-1, 4-benzoquinone (XVIIIa), 2-methyl-1, 4-naphthoquinone (XVIIIb) and 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (XVIIIc) were treated with γ, γ'-dimethoxy-carbonylvaleryl peroxide (XVII) on one step to give the esters (VIIIa, VIIIb, VIIIc) of these quinones. 2. 2, 3, 5-Trimethyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-benzoquinone (XXVa), 2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-naphthoquinone (XXVb) and 2, 3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-benzoquinone (XXVc) were synthesized by boron trifluoride-catalyzed condensation of 2, 3, 5-trimethyl-1, 4-benzohydroquinone (XXIIIa), 2-methyl-1, 4-naphthohydroquinone derivatives (XXIIIb, XXVII, XXVIII) and 2, 3-dimethoxy-5-methyl-1, 4-benzohydroquinone (XXIIIc) with methyl ε-hydroxy-γ-methyl-γ-hexenoate (XX) or methyl γ-hydroxy-γ-vinylvalerate (XXII), followed by hydrolysis of the esters to carboxylic acids and subsequent oxidation of the hydroquinones to quinones.
    描述了叶绿醌、α-生育酚和醌类化合物的代谢物的合成。1. 2, 3, 5-三甲基-6-(3'-羧基丁基)-1, 4-苯醌 (VIIa)、2-甲基-3-(3'-羧基丁基)-1, 4-萘醌 (VIIb) 和2, 3-二甲氧基-5-甲基-6-(3'-羧基丁基)-1, 4-苯醌 (VIIc) 通过两条途径合成。2, 3, 5-三甲基酚 (Ia) 和3-甲基-1-萘醇 (Ib) 与乙基琥珀酸酐 (II) 进行缩合,随后还原羰基基团并将酚氧化为醌 (VIIa, VIIb)。2, 3, 5-三甲基-1, 4-苯醌 (XVIIIa)、2-甲基-1, 4-萘醌 (XVIIIb) 和2, 3-二甲氧基-5-甲基-1, 4-苯醌 (XVIIIc) 在一步中与γ, γ'-二甲氧基-羰基戊酰过氧化物 (XVII) 处理,生成这些醌的酯 (VIIIa, VIIIb, VIIIc)。2. 2, 3, 5-三甲基-6-(5'-羧基-3'-甲基-2'-戊烯基)-1, 4-苯醌 (XXVa)、2-甲基-3-(5'-羧基-3'-甲基-2'-戊烯基)-1, 4-萘醌 (XXVb) 和2, 3-二甲氧基-5-甲基-6-(5'-羧基-3'-甲基-2'-戊烯基)-1, 4-苯醌 (XXVc) 通过三氟化硼催化的缩合反应合成,反应物包括2, 3, 5-三甲基-1, 4-苯醌醇 (XXIIIa)、2-甲基-1, 4-萘醌醇衍生物 (XXIIIb, XXVII, XXVIII) 和2, 3-二甲氧基-5-甲基-1, 4-苯醌醇 (XXIIIc) 与甲基ε-羟基-γ-甲基-γ-己烯酸酯 (XX) 或甲基γ-羟基-γ-乙烯基戊酸酯 (XXII) 反应,随后对酯进行水解生成羧酸,再将醌醇氧化为醌。
  • Regio- and stereoselective terminal allylic carboxymethylation of gem-dimethyl olefins. Synthesis of biologically important linear degraded terpenoids.
    作者:YUKIO MASAKI、KAZUHIKO SAKUMA、KENJI KAJI
    DOI:10.1248/cpb.33.1930
    日期:——
    gem-Dimethyl olefins (III) were transformed regiospecifically to the terminal β-methallyl sulfides (IV) bearing the methoxycarbonylmethyl substituent on the sulfur atom via (A) methoxycarbonylmethanesulfenyl chloride addition followed by dehydrochlorination or (B) allylic chlorination with SO2Cl2 followed by sulfenylation with methyl thioglycolate. Treatment of the sulfides (IV) with tert-BuOK or NaH in N, N-dimethylformamide or dimethyl sulfoxide at room temperature gave stereoselectively the sulfur-free esters (V) through a novel one-pot desulfurizative [2, 3]-sigmatropic rearrangement. By utilizing this method, biologically and pharmacologically important linear degraded terpenoids, a diol component (1) of the pheromonal secretion of the queen butterfly and several ω-quinoid acids (4, n=1, 2) and (5, n=1, 2), which are metabolites of polyisoprenoidquinones, were synthesized.
    gem-Dimethyl 烯烃 (III) 通过 (A) 向甲氧基羧甲烷磺酰氯的加成反应后去氯化,或 (B) 与 SO2Cl2 的烯丙基氯化反应,再与甲基硫代甘油酸酯进行硫烯基化反应,特异性地转化为带有甲氧基羧甲基取代基的末端 β-美沙酰硫化物 (IV)。在室温下,用 tert-BuOK 或 NaH 处理这些硫化物(IV)于 N,N-二甲基甲酰胺或二甲基亚砜,得到无硫的酯 (V),这一过程通过一种新颖的一锅式脱硫 [2,3]-σ-转位重排实现。利用该方法,合成了生物和药理学上重要的线性降解萜烯,蝴蝶女王的信息素分泌物中的二醇成分 (1),以及几种 ω-醌酸 (4, n=1, 2) 和 (5, n=1, 2),这些都是多异戊二烯醌的代谢物。
  • Efficient Syntheses of Vitamin K Chain-Shortened Acid Metabolites
    作者:Aaron Teitelbaum、Michele Scian、Wendel Nelson、Allan Rettie
    DOI:10.1055/s-0034-1380002
    日期:——
    Vitamin K sequentially undergoes omega-oxidation followed by successive rounds of beta-oxidation to ultimately produce two chain-shortened carboxylic acid metabolites, vitamin K acid 1 and vitamin K acid 2. Two facile syntheses of these acid metabolites are described, each starting from commercially available menadione-cyclopentadiene adduct 3. Vitamin K acid 1 was synthesized in five steps via alkylation
    维生素K依次经历ω-氧化,然后连续几轮β-氧化,最终产生两种链缩短的羧酸代谢物,即维生素K酸1和维生素K酸2。描述了这些酸代谢物的两种简便合成方法,每种均从商业上开始可用的甲萘醌-环戊二烯加合物3。在五个步骤中,通过与香叶基卤化物进行烷基化,然后进行随后的氧化反应,同时完全保留侧链2',3'-双键的反式构型,合成了维生素K酸1。维生素K酸2由3步经二甲基烯丙基氯的烷基化反应和随后的氧化反应分5步合成。
  • [EN] CARBOXYLIC ACID DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISORDERS<br/>[FR] DÉRIVÉS D'ACIDE CARBOXYLIQUE POUR LE TRAITEMENT DE TROUBLES DU STRESS OXYDATIF
    申请人:EDISON PHARMACEUTICALS INC
    公开号:WO2014194292A1
    公开(公告)日:2014-12-04
    Disclosed herein are compounds and methods of using such compounds for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging, or for modulating one or more energy biomarkers, normalizing one or more energy biomarkers, or enhancing one or more energy biomarkers, wherein the compounds are quinone or naphthoquinone compounds with carboxylic acid or carboxylic acid derivative substituents.
    本文公开了一种化合物及其使用方法,用于治疗或抑制氧化应激性疾病,包括线粒体疾病、能量处理障碍、神经退行性疾病和衰老疾病,或调节一个或多个能量生物标志物,规范一个或多个能量生物标志物,或增强一个或多个能量生物标志物,其中该化合物是带有羧酸或羧酸衍生物取代基的醌或萘醌化合物。
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