3-羟基-4-(2-丙烯基)苯甲酸甲酯 | 79950-41-7

• 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-羟基-4-(2-丙烯基)苯甲酸甲酯
• 英文名称: methyl 3-hydroxy-4-(2-propenyl)benzoate
• 英文别名: methyl 4-allyl-3-hydroxybenzoate；4-allyl-3-hydroxy-benzoic acid methyl ester；4-Allyl-3-hydroxy-benzoesaeure-methylester；methyl 3-hydroxy-4-prop-2-enylbenzoate
• CAS: 79950-41-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: FPTZYVYEKZQFIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-4-(2-丙烯基)苯甲酸甲酯 在 氯化亚砜 、 二甲基硫 、 磷酸 、 二氯乙基铝 、 臭氧 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.75h， 生成 (6-benzofuryl){1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl}methanone
  参考文献：
  名称：

  Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics

  摘要：

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).

  DOI：

  10.1021/jm00016a013
• 作为产物：
  描述：

  methyl 3-(allyloxy)benzoate 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 4.5h， 生成 3-羟基-4-(2-丙烯基)苯甲酸甲酯
  参考文献：
  名称：

  Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics

  摘要：

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).

  DOI：

  10.1021/jm00016a013

文献信息

• Design, synthesis and pharmacology of 1,1-bistrifluoromethylcarbinol derivatives as liver X receptor β-selective agonists
  作者：Minoru Koura、Takayuki Matsuda、Ayumu Okuda、Yuichiro Watanabe、Yuki Yamaguchi、Sayaka Kurobuchi、Yuuki Matsumoto、Kimiyuki Shibuya

  DOI：10.1016/j.bmcl.2015.04.080

  日期：2015.7

  A novel series of 1,3-bistrifluoromethylcarbinol derivatives that act as liver X receptor (LXR) β-selective agonists was discovered. Structure–activity relationship studies led to the identification of molecule 62, which was more effective (Emax) and selective toward LXRβ than T0901317 and GW3965. Furthermore, 62 decreased LDL-C without elevating the plasma TG level and significantly suppressed the

  发现了一系列作为肝 X 受体 (LXR) β-选择性激动剂的新型 1,3-双三氟甲基甲醇衍生物。结构-活性关系研究导致分子62的鉴定，它比 T0901317 和 GW3965 对 LXRβ更有效 ( E max ) 和选择性。此外，在 Bio F 1中， 62降低了 LDL-C 而没有提高血浆 TG 水平，并显着抑制了主动脉弓中的脂质积聚区域B 仓鼠喂食高脂肪和高胆固醇的饮食。我们证明了我们的 LXRβ 激动剂可能用作降血脂和抗动脉粥样硬化剂。在这份手稿中，我们报告了 1,3-双三氟甲基甲醇衍生物的设计、合成和药理学。
• Quinazoline derivatives
  申请人：——

  公开号：US20040044015A1

  公开（公告）日：2004-03-04

  The invention concerns quinazoline derivatives of Formula (I) wherein each of m, R 1 , n, R 2 and R 3 have any of the meanings defined in the description; process for the preparation, pharmaceutical compositions them and their use in the manufacture of a medicament for use as an anti-invasive agent in the containment and/or treatment of solid tumour disease.

  这项发明涉及式（I）的喹唑啉衍生物，其中m、R1、n、R2和R3中的每一个具有描述中定义的任意含义；制备过程，药物组合物及其在制备用作抗侵袭剂的药物中的使用，用于包含和/或治疗固体肿瘤疾病。
• SYNTHESIS OF INTERMEDIATES FOR PRODUCING PROSTACYCLIN DERIVATIVES
  申请人：United Therapeutics Corporation

  公开号：US20160107973A1

  公开（公告）日：2016-04-21

  The present disclosure provides regioselective methods for synthesizing intermediates useful in making prostacyclin derivatives, such as treprostinil.

  本公开提供了用于合成中间体的区域选择性方法，这些中间体在制备前列环素衍生物（如曲普罗斯汀）中非常有用。
• Claisen rearrangement of meta-substituted allyl phenyl ethers
  作者：J. Malcolm Bruce、Yusuf Roshan-Ali

  DOI：10.1039/p19810002677

  日期：——

  Electron-releasing substituents at the 3-position of allyl phenyl ethers favour Claisen rearrangement of the allyl group to the 6-position, whereas electron-acceptors favour migration to the 2-position. 2-Acylhydroquinone 4-allyl ethers yield, predominantly, the 3-allyl isomers, probably because internal hydrogen bonding confers naphthalenoid character on the aryl residue.

  烯丙基苯基醚3位的电子释放取代基有利于烯丙基的Claisen重排至6位，而电子受体则有利于向2位迁移。2-酰基氢醌4-烯丙基醚主要产生3-烯丙基异构体，这可能是因为内部氢键使芳基残基具有萘类特征。
• METHOD FOR THE SYNTHESIS OF 4-BENZOFURAN-CARBOXYLIC ACID
  申请人：Burgos Alain

  公开号：US20090131688A1

  公开（公告）日：2009-05-21

  The invention concerns a novel method for synthesis of 4-benzofuran-carboxylic acid or alkyl ester thereof. This method is characterized in that a reaction for aromatization of a compound of formula (II) is performed for the synthesis of the compound of formula (I), according to the scheme A2 below: wherein R independently represents hydrogen or a linear or branched C 1 - 15 alkyl group. With the invention, it is possible to industrially synthesize 4-benzofuran-carboxylic acid or alkyl ester thereof with good yield and very good purity.

  该发明涉及一种合成4-苯并呋喃羧酸或其烷基酯的新方法。该方法的特点在于，根据下面的方案A2，对式（II）化合物进行芳香化反应以合成式（I）的化合物：其中R独立表示氢或直链或支链的C1-15烷基基团。通过这项发明，可以以良好的产率和非常高的纯度工业化合成4-苯并呋喃羧酸或其烷基酯。