2-(3,5-dimethoxyphenyl)-2-methylpropanal | 120078-30-0

• 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: 2-(3,5-dimethoxyphenyl)-2-methylpropanal
• CAS: 120078-30-0
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: SGNDUMHGQHTXHH-UHFFFAOYSA-N

物化性质

• 沸点：
  310.8±37.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  室温，惰性气氛

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethoxyphenyl)-2-methylpropanal 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以94%的产率得到2-(3,5-dimethoxyphenyl)-2-methylpropan-1-ol
  参考文献：
  名称：

  Probing the Carboxyester Side Chain in Controlled Deactivation (−)-Δ⁸-Tetrahydrocannabinols

  摘要：

  We recently reported on a controlled deactivation/detoxification approach for obtaining cannabinoids with improved druggability. Our design incorporates a metabolically labile ester group at strategic positions within the THC structure. We have now synthesized a series of (-)Delta(8)-THC analogues encompassing a carboxyester group within the 3-alkyl chain in an effort to explore this novel cannabinergic chemotype for CB receptor binding affinity, in vitro and in vivo potency and efficacy, as well as controlled deactivation by plasma esterases. We have also probed the chains polar characteristics with regard to fast onset and short duration of action. Our lead molecule, namely 2-[(6aR,10aR)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-3-yl]-2-methyl-propanoic acid 3-cyano-propyl ester (AM7438), showed picomolar affinity for CB receptors and is deactivated by plasma esterases while the respective acid metabolite is inactive. In further in vitro and in vivo experiments, the compound was found to be a remarkably potent and efficacious CB1 receptor agonist with relatively fast onset/offset of action.

  DOI：

  10.1021/jm501165d
• 作为产物：
  描述：

  2-(3,5-二甲氧基苯基)丙-2-醇 在 氢溴酸 、 lithium 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(3,5-dimethoxyphenyl)-2-methylpropanal
  参考文献：
  名称：

  通过Barbier反应合成槲皮素的碳环类似物

  摘要：

  描述了到碳环类黄酮2的六步合成路线。关键步骤涉及通过Barbier反应将叔溴化物1,4-加成到α，β-不饱和酯上。

  DOI：

  10.1016/s0040-4039(01)93800-6

文献信息

• [EN] 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS<br/>[FR] LIGANDS CANNABINERGIQUES DE 2-CYCLOALKYL RÉSORCINOL
  申请人：UNIV NORTHEASTERN

  公开号：WO2014062965A1

  公开（公告）日：2014-04-24

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明涉及新型2-环烷基间苯二酚化合物；包括这些化合物的药物组合物；以及制备这些化合物和它们的用途的方法。所披露的化合物可以结合并调节大麻素受体，因此它们是这些受体的特异性配体。当将这些发明的化合物以治疗有效剂量的方式给予个体或动物时，会在个体或动物体内产生足够高水平的该化合物，从而引起生理反应。这种生理反应可能有助于治疗多种生理状况。
• [EN] PROCESS FOR THE PREPARATION OF HU-910 AND CRYSTALLINE STRUCTURE THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE HU-910 ET STRUCTURE CRISTALLINE ASSOCIÉE
  申请人：YISSUM RES DEV CO OF HEBREW UNIV JERUSALEM LTD

  公开号：WO2018087767A1

  公开（公告）日：2018-05-17

  The invention provides processes for the preparation of HU-910, which are scalable to industrial purposes, using safer reagents and having high yield and pure product and a crystalline structure of HU-910, which is a unique product thereof.

  这项发明提供了用于制备HU-910的工艺，这些工艺可扩展至工业用途，使用更安全的试剂，产率高，产品纯度高，并具有独特的结晶结构的HU-910。
• Brønsted Acid-Catalyzed Intramolecular Hydroarylation of β-Benzylstyrenes
  作者：Xiao Cai、Amir Keshavarz、Justin D. Omaque、Benjamin J. Stokes

  DOI：10.1021/acs.orglett.7b00958

  日期：2017.5.19

  triphenylmethylium tetrakis(pentafluorophenyl)borate as a convenient Brønsted acid precatalyst, β-(α,α-dimethylbenzyl)styrenes are shown to cyclize efficiently to afford a variety of new indanes that possess a benzylic quaternary center. The geminal dimethyl-containing quaternary center is proposed to be necessary to arm the substrate for cyclization through steric biasing.

  使用四（五氟苯基）硼酸三苯甲基铵作为方便的布朗斯台德酸预催化剂，β-（α，α-二甲基苄基）苯乙烯显示出有效的环化作用，从而提供了多种具有苄基季中心的新型茚满。提出了含双甲基的双季铵盐中心对于武装通过空间偏压环化的底物是必需的。
• [EN] CANNABINOIDS AND USES THEREOF<br/>[FR] CANNABINOÏDES ET LEURS UTILISATIONS
  申请人：CORBUS PHARMACEUTICALS INC

  公开号：WO2019232413A1

  公开（公告）日：2019-12-05

  The invention relates to cannabinoid compounds, pharmaceutical compositions including one or more cannabinoid compounds, and the use of pharmaceutical compositions including one or more cannabinoid compounds for the treatment of a disease or condition (e.g., a fibrotic disease or an inflammatory disease) in a subject in need thereof.

  该发明涉及大麻素化合物、包括一个或多个大麻素化合物的药物组合物，以及利用包括一个或多个大麻素化合物的药物组合物治疗患有疾病或症状（例如，纤维化疾病或炎症性疾病）的患者的用途。
• Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers
  作者：Chiara Zanato、Alessia Pelagalli、Katie F. M. Marwick、Monica Piras、Sergio Dall'Angelo、Andrea Spinaci、Roger G. Pertwee、David J. A. Wyllie、Giles E. Hardingham、Matteo Zanda

  DOI：10.1039/c6ob02796b

  日期：——

  the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl D-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile

  我们报告了末端氟化的HU-210和HU-211类似物（分别为HU-210F和HU-211F ）的合成及其作为大麻素受体（CB 1和 CB 2）和N-甲基D-天冬氨酸受体配体的生物学评价(NMDAR)。[ 18 F] -标记的HU- 210F由溴取代的前体放射合成。体外试验表明HU-210F和HU-211F都保留了HU-210和HU-211的有效药理学特征，这表明 [18 F] -放射性标记的 HU- 210F和HU-211F可能具有作为体内成像 PET 示踪剂的潜力。