4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile | 70770-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile
• 英文别名: 4-(3,4-dimethoxy-phenyl)-4-oxo-butyronitrile；4-Oxo-4-(3.4-dimethoxy-phenyl)-buttersaeure-nitril
• CAS: 70770-03-5
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD10037684
• 分子量: 219.24
• InChiKey: VXADXTFGDCLVIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile 在 盐酸 、 乙醇 、 羟胺 作用下， 生成 [5-(3,4-dimethoxy-phenyl)-pyrrol-2-yl]-[5-(3,4-dimethoxy-phenyl)-pyrrol-2-yliden]-amine
  参考文献：
  名称：

  225. β -Cycloylpropionitriles。第二部分 转化为双-2-（5-环基吡咯）氮杂吗啉盐

  摘要：

  DOI：

  10.1039/jr9470001196
• 作为产物：
  描述：

  4-(3,4-dimethoxyphenyl)-4-nitrobutanenitrile 在 potassium hydroxide 、 potassium permanganate 、 水 作用下， 以 甲醇 为溶剂， 以88%的产率得到4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile
  参考文献：
  名称：

  KMnO₄-Mediated Oxidation as a Continuous Flow Process

  摘要：

  An efficient and easily scalable transformation of alcohols and aldehydes to carboxylic acids and nitroalkane derivatives to the corresponding carbonyls and carboxylic acids using permanganate as the oxidant within a continuous flow reactor is reported. Notably, the generation and downstream processing of MnO2 slurries was not found to cause any blocking of the reactor when ultrasound pulses were applied to the flow system.

  DOI：

  10.1021/ol101345z

文献信息

• Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
  申请人：CytoMed Incorporated

  公开号：US06201016B1

  公开（公告）日：2001-03-13

  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.

  本发明揭示了对映富集的二取代四氢呋喃、四氢噻吩、吡咯烷和环戊烷，可减少在炎症或免疫反应期间多形核白细胞的趋化和呼吸爆发，从而导致有害氧自由基的形成。这些化合物通过作为PAF受体拮抗剂、抑制酶5-脂氧化酶或表现出双重活性即既作为PAF受体拮抗剂又作为5-脂氧化酶抑制剂而表现出这种生物活性。已经确定，所述化合物的光学异构体中，5-脂氧化酶活性、口服可用性和体内稳定性（例如，葡萄糖醛酸化速率）可以有显著差异。
• 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。
• �ber die Sulfitkochung von Phenylpropanderivaten
  作者：K. Kratzl、H. D�ubner、U. Siegens

  DOI：10.1007/bf00899006

  日期：——
• 46. β-Cycloylpropionitriles. Part III. Reduction to 2-cyclyl-Δ²-pyrrolines and 2-cyclylpyrrolidines
  作者：Edward B. Knott

  DOI：10.1039/jr9480000186

  日期：——