5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one | 14335-78-5

• 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: 5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one
• 英文别名: 5-(3, 4-dimethoxyphenyl)dihydrofuran-2-one；γ-<3,4-Dimethoxy-phenyl>-γ-butyrolacton；5-<3,4-Dimethoxy-phenyl>-4,5-dihydro-furan-2-on；5-(3,4-Dimethoxy-phenyl)-dihydro-furan-2-on；4-(3',4'-dimethoxyphenyl)butyrolactone；5-(3,4-dimethoxyphenyl)oxolan-2-one
• CAS: 14335-78-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: WUTCRAWYHFZCPK-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  384.0±42.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one 、 2,6-二甲基-2,5-环己二烯-1,4-二酮 在 二氢吡啶 、 hafnium tetrakis(trifluoromethanesulfonate) 作用下， 反应 2.5h， 以96%的产率得到4-(3,5-dimethyl-1,4-benzoquinon-2-yl)-4-(3,4-dimethoxylphenyl)butyric acid
  参考文献：
  名称：

  内酯与醌的催化氧化还原链开环合成含醌的羧酸

  摘要：

  五至八元内酯与醌的催化开环是通过氧化还原链机理实现的。在简单的三氟甲磺酸金属路易斯酸催化剂和链引发剂的低负载下，许多醌的C–H键被含羧酸的侧链有效地官能化。该方法还具有100％的原子经济性和广泛的底物范围。开发了一种抗哮喘药Seratrodast的新途径。机理研究表明，氧化还原链反应可能发生碳正离子中间体。

  DOI：

  10.1021/acs.orglett.9b01672
• 作为产物：
  描述：

  4-(3,4-二甲氧苯基)丁酸 在 potassium 12-tungstocobalt(III)ate 作用下， 以 水 为溶剂， 生成 5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one
  参考文献：
  名称：

  水溶液中环甲氧基化芳基链烷酸自由基阳离子和自由基两性离子的反应性和酸碱行为。结构效应和pH值对苯甲酰CH去质子化途径的影响†

  摘要：

  在不同的pH值下，对环甲氧基化的苯丙酸和苯丁酸（Ar（CH 2）n CO 2 H，n = 2、3）进行单电子氧化的产物和时间分辨动力学研究。氧化导致芳族基团的阳离子的形成（AR • +（CH 2）Ñ CO 2 H）或基团的两性离子（AR • +（CH 2）ñ CO 2 - ），这取决于pH值，且p ķ一个已测量了相应的酸碱平衡值。在自由基阳离子中，通过增加甲氧基环取代基的数目和通过增加羧基与芳环之间的距离，羧基质子的酸度降低。如产物分析结果清楚地显示，在pH值为1.7或6.7时，自由基阳离子或两性离子会经历苄基CH去质子化，作为唯一的侧链断裂途径。在pH 1.7下，对环甲氧基化的芳基链烷酸自由基阳离子测得的一阶去质子化速率常数与先前在酸性水溶液中对与结构相关的环甲氧基化的烷基芳族自由基阳离子的α-CH脱质子化所测得的常数相似。在基本解决方案中，获得了-OH（k - OH）。这些值类似于针对

  DOI：

  10.1021/jo060678i

文献信息

• Compounds and methods for the treatment of cardiovascular, inflammatory
  申请人：Cytomed, Inc.

  公开号：US05681966A1

  公开（公告）日：1997-10-28

  Enantiomerically enriched disubstituted tetrahydrofurans, tetrahydrothiophenes, pyrrolidines and cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. It has been determined that 5-lipoxygenase activity, oral availability, and stability in vivo (for example, glucuronidation rate) can vary significantly among the optical isomers of the disclosed compounds.

  本文披露了具有对多形核白细胞在炎症或免疫反应中导致有害氧自由基形成的趋化性和呼吸爆发的还原二取代四氢呋喃，四氢噻吩，吡咯烷和环戊烷的对映体富集化合物。这些化合物通过作为PAF受体拮抗剂，抑制5-脂氧合酶酶或表现出双重活性，即既作为PAF受体拮抗剂又作为5-脂氧合酶抑制剂来表现出这种生物活性。已经确定，所披露的化合物的光学异构体中，5-脂氧合酶活性、口服可用性和体内稳定性（例如，葡萄糖醛酸化速率）可能会有显著的差异。
• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF CARDIOVASCULAR, INFLAMMATORY AND IMMUNE DISORDERS<br/>[FR] COMPOSES ET PROCEDES POUR LE TRAITEMENT DES TROUBLES CARDIO-VASCULAIRES, INFLAMMATOIRES ET IMMUNITAIRES
  申请人：CYTOMED, INC.

  公开号：WO1996000212A1

  公开（公告）日：1996-01-04

  (EN) Tetrahydrofurans, tetrahydrothiophenes, pyrrolidines and cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. It has been determined that 5-lipoxygenase activity, oral availability, and stability $i(in vivo) (for example, glucuronidation rate) can vary significantly among the optical isomers of the disclosed compounds.(FR) L'invention concerne des tétrahydrofurannes, des tétrahydrothiophènes, des pyrrolidines et des cyclopentanes qui réduisent le chimiotactisme et l'activation métabolique respiratoire entraînant la formation de radicaux oxygène dommageables de leucocytes polymorphonucléaires lors d'une réaction inflammatoire ou immunitaire. Ces composés présentent cette activité biologique en agissant comme antagonistes du récepteur du facteur d'activation des plaquettes, en inhibant la 5-lipoxygénase, ou bien en présentant une activité double, c'est-à-dire en agissant à la fois comme antagonistes du récepteur du facteur d'activation des plaquettes et comme inhibiteur de la 5-lipoxygénase. Il a été déterminé que l'activité 5-lipoxygénase, la disponibilité orale, et la stabilité $i(in vivo)(par exemple le taux de glucuronidation) peuvent varier substantiellement parmi les isomères optiques descomposés décrits.

  （中文）本发明揭示了四氢呋喃、四氢噻吩、吡咯烷和环戊烷等化合物，它们能够减少炎症或免疫反应中多形核白细胞趋化和呼吸爆发，从而防止有害氧自由基的形成。这些化合物通过作为PAF受体拮抗剂、抑制5-脂氧合酶酶或双重作用（即同时作为PAF受体拮抗剂和5-脂氧合酶抑制剂）来展现这种生物活性。已经确定，这些化合物的光学异构体中，5-脂氧合酶活性、口服可用性和稳定性（例如葡萄糖醛酸化率）可以有显著差异。
• 4‐(Dimethylamino)Pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid
  作者：Ivan A. Andreev、Maksim A. Boichenko、Nina K. Ratmanova、Olga A. Ivanova、Irina I. Levina、Victor N. Khrustalev、Igor A. Sedov、Igor V. Trushkov

  DOI：10.1002/adsc.202200486

  日期：2022.7.19

  We report a procedure for the multigram synthesis of 4-(dimethylamino)pyridinium azide, a stable, non-explosive, low-hygroscopic source of azide ion soluble in both protic and aprotic organic solvents. In protic ionic liquid media this reagent was shown to serve as a safer equivalent of toxic and unstable hydrazoic acid. The synthetic utility of this system was demonstrated using donor-acceptor cyclopropane

  我们报告了一种多克合成 4-(二甲氨基) 叠氮化吡啶鎓的过程，这是一种稳定、非爆炸性、低吸湿性的叠氮化物离子源，可溶于质子和非质子有机溶剂。在质子离子液体介质中，该试剂被证明可作为有毒且不稳定的叠氮酸的更安全等效物。使用供体-受体环丙烷开环作为模型过程证明了该系统的合成效用。详细说明了根据所应用的质子离子液体提供各种 (2-叠氮基-2-芳乙基) 丙二酸二烷基酯或 4-叠氮基-4-芳基丁酸二烷基酯的一般程序。建立所研究的供体-受体环丙烷的转化时间，提供相对反应性序列。4-(二甲氨基)吡啶叠氮在常规亲核取代、环氧乙烷开环中的应用，
• Lewis and Brönsted acid catalyzed Friedel–Crafts hydroxyalkylation of mucohalic acids: a facile synthesis of functionalized γ-aryl γ-butenolides
  作者：Ji Zhang、Peter G. Blazecka、Timothy T. Curran

  DOI：10.1016/j.tetlet.2007.02.009

  日期：2007.4

  A catalytic, green and practical method for Friedel-Crafts hydroxyalkylation of mucohalic acid has been accomplished. Reaction of mucohalic acids with various electron-rich aromatic compounds in the presence of catalytic (1 mol % to 10 mol %) In(OTf)(3) or Bronsted acid, such as H2SO4 in acetic acid provides gamma-aryl gamma-butenolides in moderate to excellent yield. (c) 2007 Elsevier Ltd. All rights reserved.
• Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones
  作者：Barry M. Trost、Young H. Rhee

  DOI：10.1021/ja992013m

  日期：1999.12.1

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).