2-(3,5-dihydroxyphenyl)propanoic acid | 101479-13-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(3,5-dihydroxyphenyl)propanoic acid
• CAS: 101479-13-4
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: TUUMABKIYSPWKU-UHFFFAOYSA-N

物化性质

• 沸点：
  404.8±14.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-dihydroxyphenyl)propanoic acid 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.2h， 生成 (2R)-2-[(6aR,10aR)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-3-yl]propanoic acid butyl ester
  参考文献：
  名称：

  Controlled-Deactivation Cannabinergic Ligands

  摘要：

  We report an approach for obtaining novel cannabinoid analogues with controllable deactivation and improved druggability. Our design involves the incorporation of a metabolically labile ester group at the 2'-position on a series of (-)-Delta(8)-THC analogues. We have sought to introduce benzylic substituents a to the ester group which affect the half-lives of deactivation through enzymatic activity while enhancing the affinities and efficacies of individual ligands for the CB1 and CB2 receptors. The 1'-(S)-methyl, 1'-gem-dimethyl, and 1'-cyclobutyl analogues exhibit remarkably high affinities for both CB receptors. The novel ligands are susceptible to enzymatic hydrolysis by plasma esterases in a controllable manner, while their metabolites are inactive at the CB receptors. In further in vitro and in vivo experiments key analogues were shown to be potent CB1 receptor agonists and to exhibit CBI-mediated hypothermic and analgesic effects.

  DOI：

  10.1021/jm4016075
• 作为产物：
  描述：

  2-(3,5-dimethoxyphenyl)propanoic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以78%的产率得到2-(3,5-dihydroxyphenyl)propanoic acid
  参考文献：
  名称：

  Controlled-Deactivation Cannabinergic Ligands

  摘要：

  We report an approach for obtaining novel cannabinoid analogues with controllable deactivation and improved druggability. Our design involves the incorporation of a metabolically labile ester group at the 2'-position on a series of (-)-Delta(8)-THC analogues. We have sought to introduce benzylic substituents a to the ester group which affect the half-lives of deactivation through enzymatic activity while enhancing the affinities and efficacies of individual ligands for the CB1 and CB2 receptors. The 1'-(S)-methyl, 1'-gem-dimethyl, and 1'-cyclobutyl analogues exhibit remarkably high affinities for both CB receptors. The novel ligands are susceptible to enzymatic hydrolysis by plasma esterases in a controllable manner, while their metabolites are inactive at the CB receptors. In further in vitro and in vivo experiments key analogues were shown to be potent CB1 receptor agonists and to exhibit CBI-mediated hypothermic and analgesic effects.

  DOI：

  10.1021/jm4016075

文献信息

• STABLE HOMOGENEOUSLY MIXED NANOSCALE COATINGS DERIVED FROM UNIQUE MULTI-FUNCTIONAL AND MULTIDENTATE AROMATIC ADSORBATES
  申请人：THE UNIVERSITY OF HOUSTON SYSTEM

  公开号：US20130327251A1

  公开（公告）日：2013-12-12

  Novel tridentate-, bidentate-, and monodentate-based aromatic adsorbates including self-assembled monolayers (SAMs), especially, mixed multi-component SAMs, where the adsorbates comprise an aromatic ring including one head group or a plurality of dentate head groups and one tunable tail group or a plurality of tail groups and methods for making the same, and methods for using same, their use in the preparation of homogeneously mixed multi-component self-assembled monolayers (SAMs). The adsorbants and SAMs derived therefrom are ideally suited for biosensing, biosensing diagnostics, biological interfacial mimics, surface protections for nanoparticles, inert coatings for artificial implants, and corrosion-resistant coatings for microelectronics components.

  包括自组装单分子膜（SAMs）在内的新型三齿、双齿和单齿基芳香吸附剂，特别是混合多组分SAMs，其中吸附剂包括一个含有一个头基或多个牙基和一个可调节尾基或多个尾基的芳香环，并制备方法，以及使用相同的方法，它们在制备均匀混合多组分自组装单分子膜（SAMs）中的用途。由此产生的吸附剂和SAMs非常适用于生物传感、生物传感诊断、生物界面模拟、纳米颗粒的表面保护、人工植入物的惰性涂层以及微电子元件的耐蚀涂层。
• Synthesis of C-3 side-chain carboxylic acid cannabinoid derivatives
  作者：Ronald F. Borne、Scott C. Mauldin

  DOI：10.1002/jhet.5570220315

  日期：1985.5

  Based upon the structural similarities of cannabinoid derivatives which inhibit the biosynthesis of prostaglandins with those of the potent inhibitor, indomethacin, several cannabinoid derivatives possessing C-3 side chain carboxylic acid functionalities were prepared.

  基于抑制前列腺素与强效抑制剂吲哚美辛生物合成的大麻素衍生物的结构相似性，制备了几种具有C-3侧链羧酸官能团的大麻素衍生物。
• [EN] NOVEL CANNABINERGIC COMPOUNDS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS CANNABINERGIQUES ET LEURS UTILISATIONS
  申请人：UNIV NORTHEASTERN

  公开号：WO2014039042A1

  公开（公告）日：2014-03-13

  Disclosed are compounds and compositions that modulate cannabinoid receptors, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors. This disclosure is directed to methods of treating cannabinoid dependence, neuropathy, inflammation, glaucoma, a neurodegenerative disorder, a motor function disorder, a gastrointestinal disorder, hypothermia, emesis, loss of appetite, or anorexia associated with AIDS.

  本发明涉及调节大麻素受体的化合物和组合物、调节大麻素受体的方法以及治疗与调节大麻素受体有关的各种疾病的方法。本公开涉及治疗大麻素依赖、神经病变、炎症、青光眼、神经退行性疾病、运动功能障碍、胃肠道疾病、低温、呕吐、食欲不振或艾滋病相关的厌食症的方法。
• Antioxidants
  申请人：Rudolph Thomas

  公开号：US20080152603A1

  公开（公告）日：2008-06-26

  The present invention relates to the use of compounds of the formula (I), with radicals defined in the description, as antioxidants, to corresponding novel compounds and compositions, and to corresponding processes for the preparation of compounds and compositions.

  本发明涉及使用式(I)中定义的基团化合物作为抗氧化剂，涉及对应的新型化合物和组合物，以及制备这些化合物和组合物的对应过程。
• Uv Protection
  申请人：Rudolph Thomas

  公开号：US20080171004A1

  公开（公告）日：2008-07-17

  The present invention relates to the use of compounds which do not themselves exhibit significant UV absorption in the UV-A or UV-B region, but are reactive under use conditions, for the development of UV-A or UV-B protection during use, to corresponding novel compounds and compositions, and to corresponding processes for the preparation of compounds and compositions.

  本发明涉及使用那些本身在UV-A或UV-B区域不表现出显著UV吸收但在使用条件下具有反应性的化合物用于开发UV-A或UV-B保护，以及相应的新化合物和组合物，以及制备化合物和组合物的相应过程。