(3,4-dimethoxy-phenyl)-glyoxylonitrile | 65961-86-6

• 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: (3,4-dimethoxy-phenyl)-glyoxylonitrile
• 英文别名: (3.4-Dimethoxy-phenyl)-glyoxylsaeure-nitril；Veratroylcyanid；3.4-Dimethoxy-benzoylcyanid；3,4-dimethoxybenzoyl cyanide
• CAS: 65961-86-6
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: ZUDVDNNIRVQAGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (3,4-dimethoxy-phenyl)-glyoxylonitrile 在 sodium hydroxide 、 钯 、 溶剂黄146 作用下， 生成 (3,4-dimethoxy-phenyl)-acetic acid-(β-hydroxy-3,4-dimethoxy-phenethylamide)
  参考文献：
  名称：

  Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen III. Über die Synthese von Adrenalin und von adrenalinähnlichen Verbindungen

  摘要：

  DOI：

  10.1002/ardp.19312693504
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 (3,4-dimethoxy-phenyl)-glyoxylonitrile
  参考文献：
  名称：

  Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen III. Über die Synthese von Adrenalin und von adrenalinähnlichen Verbindungen

  摘要：

  DOI：

  10.1002/ardp.19312693504

文献信息

• Ruthenium-Catalyzed Oxidations for Selective Syntheses of Ketones and Acyl Cyanides. Selective Acylation of Amino Compounds with Acyl Cyanides
  作者：Shun-Ichi Murahashi、Takeshi Naota

  DOI：10.1055/s-1993-25877

  日期：——

  Oxidation of alcohols to the corresponding carbonyl compounds with tert-butyl hydroperoxide in the presence of dichlorotris(triphenylphosphine)ruthenium catalyst gives the corresponding carbonyl compounds with high efficiency. This method can be applied to the oxidation of cyanohydrins to give acyl cyanides which are versatile synthetic intermediates. Acylation of amino compounds with acyl cyanides thus obtained proceeds chemoselectively. Thus, the reaction of amino alcohols with acyl cyanides gives N-acylated products exclusively. In the similar N-acylation of polyamines primary amines are selectively acylated in the presence of secondary amines. These reactions are highly useful for the synthesis of spermidine and spermine alkaloids such as spermidine siderophores. Dimeric cyclocoupling reaction of diacyl cyanides such as iso- and terephthaloyl cyanides with polyamines can be performed under the similar reaction conditions to give the corresponding polyazamacrocycles with high efficiency.

  在二氯三(三苯基膦)钌催化剂存在下，以叔丁基过氧化氢将醇氧化为相应的羰基化合物，具有高效率。此方法可应用于氰醇的氧化，生成通用的合成中间体酰基氰化物。由此获得的酰基氰化物对氨基酸化合物进行的酰化反应具有化学选择性。因此，氨基酸醇与酰基氰化物的反应仅生成N-酰化产物。类似地，在次级胺存在下，多胺的N-酰化反应中初级胺被选择性酰化。这些反应对于合成如多胺铁载体等多胺类生物碱非常有益。在相似的反应条件下，二酰基氰化物如异酞酰氰化物和萘酞酰氰化物与多胺的二聚环化反应可高效地生成相应的多氮大环化合物。
• [EN] CYCLIC TRIAZO AND DIAZO SODIUM CHANNEL BLOCKERS<br/>[FR] BLOQUEUR DE CANAUX SODIQUES TRIAZOÏQUES ET DIAZOÏQUES CYCLIQUES
  申请人：UNIV GREENWICH

  公开号：WO2009090431A1

  公开（公告）日：2009-07-23

  Compounds of general structure in which X and Y are each N or C with at least one of X and Y being N; Z is a single bond or an optionally substituted linking group R1 is hydrogen or a substituent group; R2 is amino or a substituent group; N* is amino when RI is hydrogen or =NH when R1 is a substituent group; or N* is a group NRaRb where Ra and Rb are independently H or an alkyl group; or N* is an optionally substituted piperazinyl ring; and A is an optionally substituted heterocyclic or carbocyclic ring system which may be linked to the triazo/diazo ring through R2 to form a fused multicyclic ring; are indicated as suitable for treatment of disorders in mammals that are susceptible to sodium channel blockers and antifolates, and particularly disorders such epilepsy, multiple sclerosis, glaucoma and uevitis, cerebral traumas and cerebral ischaemias, stroke, head injury, spinal cord injury, surgical trauma, neurodegenerative disorders, motorneurone disease, Alzheimer's disease, Parkinson's disease, chronic inflammatory pain, neuropathic pain, migraine, bipolar disorder, mood, anxiety and cognitive disorders, schizophrenia and trigeminal autonomic cephalalgias; for treatment of mammalian cancers; and for treatment of malaria.

  通用结构化合物，其中X和Y分别为N或C，至少X和Y中的一个为N；Z是单键或可选择性取代的连接基团；R1是氢或取代基团；R2是氨基或取代基团；N*是氨基，当R1为氢或=NH时，当R1为取代基团时；或N*是一个NRaRb基团，其中Ra和Rb分别为H或烷基基团；或N*是一个可选择性取代的哌嗪环；A是一个可选择性取代的杂环或碳环系统，可以通过R2与三唑/重氮环连接形成融合的多环环；适用于治疗对钠通道阻滞剂和抗叶酸类药物敏感的哺乳动物的疾病，特别是癫痫、多发性硬化、青光眼和葡萄膜炎、脑外伤和脑缺血、中风、头部损伤、脊髓损伤、手术创伤、神经退行性疾病、运动神经元疾病、阿尔茨海默病、帕金森病、慢性炎症性疼痛、神经病性疼痛、偏头痛、双相情感障碍、情绪、焦虑和认知障碍、精神分裂症和三叉神经自主性头痛；用于治疗哺乳动物癌症；以及用于治疗疟疾。
• Reactions between hydroxylamines and aroyl cyanides
  作者：S. Prabhakar、A.M. Lobo、M.M. Marques

  DOI：10.1016/s0040-4039(00)87114-2

  日期：1982.1

  Aromatic hydroxylamines and sterically bulky aliphatic hydroxylamines react with aroyl cyanides to give exclusively the O-acyl derivatives.

  芳族羟胺和空间上庞大的脂族羟胺与芳酰基氰化物反应，仅得到O-酰基衍生物。
• Chemoselective Acylation of Primary Amines in the Presence of Secondary Amines with Acyl Cyanides. Highly Efficient Methods for the Synthesis of Spermidine and Spermine Alkaloid
  作者：Shun-Ichi Murahashi、Takeshi Naota、Nobuyuki Nakajima

  DOI：10.1246/cl.1987.879

  日期：1987.5.5

  Acyl cyanides are highly useful reagents for the chemoselective acylation of primary amines in the presence of secondary amines. The reaction provides the versatile method for the short-step synthesis of various naturally occurring polyamines.

  酰基氰化物是在仲胺存在下化学选择性酰化伯胺的非常有用的试剂。该反应为各种天然多胺的短步合成提供了通用方法。
• Solvent vapour induced rare single-crystal-to-single-crystal transformation of stimuli-responsive fluorophore: Solid state fluorescence tuning, switching and role of molecular conformation and substituents
  作者：Palamarneri Sivaraman Hariharan、Chengjun Pan、Subramanian Karthikeyan、Dexun Xie、Akira Shinohara、Chuluo Yang、Lei Wang、Savarimuthu Philip Anthony

  DOI：10.1016/j.dyepig.2019.108067

  日期：2020.3

  formation of fluorescent polymorphs and SC-SC transition exhibited tunable and switchable solid state fluorescence. The non-planar TPE core has been made use to demonstrate high contrast stimuli induced reversible fluorescence switching. Overall, the present studies attempted to gain information on the structural design for developing SC-SC transforming functional organic fluorescent materials that

  超分子相互作用和分子构象在产生荧光多晶型物方面起着重要作用，该荧光多晶型物具有来自单个荧光团的固态可调发射。外部刺激诱导的从一种多晶型物到另一种多晶型物的结构转变而不会失去单晶特性（单晶到单晶转变（SC-SC））提供了一个理想的模型，以了解固态分子的结构特性和设计新的功能性荧光材料。在本文中，我们量身定制了基于聚集诱导发射（AIE）的四苯基乙烯（TPE）供体（D）-受体（A）荧光团（TPPA-1-6）的取代基，并探讨了荧光多晶型物的形成和SC-SC的转变固态。TPPA-1通过TPE苯基和氰基苯基受体苯环之间的扭曲和共面构象显示了构象荧光多晶型物。但是，其他衍生物的单晶分析表明，取代基和超分子相互作用控制分子构象和SC-SC过渡。具有相同取代基但位置变化的荧光团也对荧光多晶型物的形成和SC-SC转变表现出强烈的影响。可以形成强分子间相互作用的取代基稳定了不稳定的共平面结构，而具有弱分子间相互