3-烯丙基-4-甲氧基-苯甲醛 | 67483-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-烯丙基-4-甲氧基-苯甲醛
• 英文名称: 3-allyl-4-methoxybenzaldehyde
• 英文别名: 4-methoxy-3-prop-2-enylbenzaldehyde
• CAS: 67483-48-1
• 化学式: C₁₁H₁₂O₂
• mdl: MFCD08691767
• 分子量: 176.215
• InChiKey: KBXMYFVAWMPGAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2912499000

反应信息

• 作为反应物：
  描述：

  3-烯丙基-4-甲氧基-苯甲醛 在 sodium acetate 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 2-[4-methoxy-3-(prop-2-en-1-yl)phenyl]-2,3-dihydro-4H-1-benzopyran-4-one
  参考文献：
  名称：

  用于合成异黄酮天然产物的 2,3-氧化芳基重排的范围和应用

  摘要：

  为了合成天然存在的异黄酮，研究了黄烷酮与高价碘试剂的反应。与之前的几篇文献报道相反，我们没有观察到通过环收缩途径形成任何苯并呋喃，但只能分离出异黄酮（由氧化 2,3-芳基重排产生）和黄酮（由氧化的 2,3-芳基重排产生）黄烷酮。虽然 2,3-氧化重排允许合成有用的方法来处理一些异黄酮天然产物，因为所需的起始材料很方便，但总体合成效用和反应的普遍性似乎比以前的文献报告所暗示的要有限。

  DOI：

  10.1021/acs.joc.1c01375
• 作为产物：
  描述：

  4-(3-甲基-2-丁烯氧基)苯甲醛 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 反应 23.0h， 生成 3-烯丙基-4-甲氧基-苯甲醛
  参考文献：
  名称：

  Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.061

文献信息

• [EN] PYRROLO-BENZO-1,4-DIAZINES USEFUL AS SODIUM CHANNEL BLOCKERS<br/>[FR] PYRROLO-BENZO-1,4-DIAZINES UTILES EN TANT QUE BLOQUEURS DE CANAUX SODIQUES
  申请人：SCHERING CORP

  公开号：WO2010151595A1

  公开（公告）日：2010-12-29

  Pyrrolo-benzo-1,4-diazine compounds represented by Formula I or II, or pharmaceutically acceptable salts thereof, are blockers of voltage-gated sodium channels. Pharmaceutical compositions comprise an effective amount of the instant compounds, either alone, or in combination with one or more other therapeutically active compounds, and a pharmaceutically acceptable carrier. Methods of treating conditions associated with, or caused by, voltage-gated sodium channel activity, including, for example, acute pain, chronic pain, visceral pain, inflammatory pain, neuropathic pain, epilepsy or epilepsy conditions, irritable bowel syndrome, depression, anxiety, bipolar disorder, neurodegenerative disorders, psychiatric disorders, myotonia, arrhythmia, movement disorders, neuroendocrine disorders, ataxia, multiple sclerosis, irritable bowel syndrome, incontinence, neuropathy and tinnitus, comprise administering an effective amount of the present compounds, either alone, or in combination with one or more other therapeutically active compounds.

  由公式I或II表示的吡咯-苯并-1,4-二嗪化合物或其药学上可接受的盐是电压门控钠通道的阻滞剂。药物组合物包括即时化合物的有效量，可以单独使用，也可以与一个或多个其他治疗活性化合物结合，并且包含药学上可接受的载体。治疗与电压门控钠通道活性相关或由此引起的疾病的方法，包括例如急性疼痛、慢性疼痛、内脏疼痛、炎症性疼痛、神经病性疼痛、癫痫或癫痫症状、肠易激综合征、抑郁症、焦虑症、躁郁症、神经退行性疾病、精神疾病、肌张力过高、心律失常、运动障碍、神经内分泌失调、共济失调、多发性硬化、肠易激综合征、尿失禁、神经病和耳鸣，包括单独或与一个或多个其他治疗活性化合物结合的即时化合物的有效量。
• New Stable Backbone Linker Resins for Solid-Phase Peptide Synthesis
  作者：Wenxin Gu、Richard B. Silverman

  DOI：10.1021/ol027212g

  日期：2003.2.1

  see text] Two new 4-methoxybenzaldehyde backbone linker resins were developed for the solid-phase synthesis of peptides. The linkers are very stable during the cleavage of common protecting groups for amines (Fmoc, Boc) and carboxylic acids (Me, All, tBu) in peptide synthesis. Cleavage from the resin with refluxing TFA is sufficiently mild for peptides containing polar and nonpolar amino acids.

  [反应：见正文]开发了两种新型的4-甲氧基苯甲醛骨架连接树脂，用于肽的固相合成。在裂解肽合成中的胺（Fmoc，Boc）和羧酸（Me，All，tBu）的常见保护基时，连接基非常稳定。对于含有极性和非极性氨基酸的肽，用回流的TFA从树脂上切割下来是足够温和的。
• 一类含烯丙基的单羰基姜黄素类似物在制备抗 炎药物中的应用
  申请人：温州医科大学

  公开号：CN103524318B

  公开（公告）日：2016-04-13

  本发明提供了具有抗炎作用的含烯丙基的单羰基姜黄素类似物。另外，本发明还提供了这些化合物的药物组合物以及抗炎用途等。
• Total Syntheses of Prenylated Isoflavones from <i>Erythrina sacleuxii</i> and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F
  作者：George Kwesiga、Alexandra Kelling、Sebastian Kersting、Eric Sperlich、Markus von Nickisch-Rosenegk、Bernd Schmidt

  DOI：10.1021/acs.jnatprod.0c00932

  日期：2020.11.25

  The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4′-methoxy-3′-prenylisoflavone) and erysubin F (7,4′-dihydroxy-8,3′-diprenylisoflavone) were synthesized for the first time, starting from mono- or di-O-allylated chalcones, and the structure of 5-deoxy-3′-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis.

  首次合成了异黄酮 5-deoxyprenylbiochanin A (7-hydroxy-4'-methoxy-3'-prenylisoflavone) 和 erysubin F (7,4'-dihydroxy-8,3'-diprenylisoflavone)。 - 或二-O-烯丙基化查耳酮，5-脱氧-3'-异戊二烯生物链素A的结构通过单晶X射线衍射分析得到证实。黄烷酮是合成中的关键中间体。它们与高价碘试剂反应通过 2,3-氧化重排得到异黄酮，通过 2,3-脱氢得到相应的黄酮异构体。这使得合成 7,4'-二羟基-8,3'-二异戊二烯黄酮，一种赤霉素 F 的非天然区域异构体。 Erysubin F ( 8 ), 7,4'-二羟基-8,3'-二异戊二烯黄酮 ( 27 ) , 和 5-deoxy-3'-prenylbiochanin A (7 ) 针对三种细菌菌株和一种真菌病原体进行了测试。所有
• Meta-bridged styryloxy resins
  申请人：Loctite (Ireland) Limited

  公开号：US04640849A1

  公开（公告）日：1987-02-03

  Polyfunctional cationically polymerizable styryloxy compounds of the formula ##STR1## where R.sup.1 is H or methyl; R.sup.2 is hydrocarbyl, hydrocarbyl interrupted by ether oxygen atoms, or halo substituted hydrocarbyl; R.sup.3 is H, lower alkyl, or alkoxy; G is any multivalent organic or inorganic radical free of amino or aliphatic thiol groups; and n is an integer of two or more.

  式为##STR1##的多官能阳离子可聚合的苯乙烯氧基化合物，其中R1为H或甲基; R2为烃基，被醚氧原子中断的烃基，或卤代烃基; R3为H，低烷基或烷氧基; G为任何没有氨基或脂肪硫基的多价有机或无机基团; n为2或更多的整数。