2,5-dihydroxy-3,4,6-trimethyl-benzaldehyde | 53711-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dihydroxy-3,4,6-trimethyl-benzaldehyde
• 英文别名: 2,5-Dihydroxy-3,4,6-trimethyl-benzaldehyd；Formyl-trimethyl-hydrochinon；2,5-Dihydroxy-3,4,6-trimethylbenzaldehyde
• CAS: 53711-21-0
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD24674113
• 分子量: 180.203
• InChiKey: PAWLKOOZXUMOIB-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C(Solv: ethanol (64-17-5))
• 沸点：
  309.6±37.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dihydroxy-3,4,6-trimethyl-benzaldehyde 在 乙醇 、 sodium ethanolate 、 sodium acetate 作用下， 生成 6-hydroxy-5,7,8-trimethyl-coumarin
  参考文献：
  名称：

  Manecke; Bourwieg, Chemische Berichte, 1959, vol. 92, p. 2958,2960

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氢醌 在 盐酸 、 氢氧化钾 、 三氯化铝 、 乙醇 、 苯 作用下， 生成 2,5-dihydroxy-3,4,6-trimethyl-benzaldehyde
  参考文献：
  名称：

  John; Guenther, Chemische Berichte, 1939, vol. 72, p. 1649,1652

  摘要：

  DOI：

文献信息

• The generation of C,O,O-trilithiated derivatives of dihydric phenols
  作者：José M. Saá、Jeroni Morey、Guillem Suñer、Antoni Frontera、Antoni Costa

  DOI：10.1016/0040-4039(91)80507-3

  日期：1991.12

  Halogenated dihydric phenols (hydroquinones and resorcinols) undergo halogen metal exchange with nBuLi/TMEDA/THF or ether (inverse addition) under sonication, thereby generating a C,O,O-trilithiated species which can be trapped with electrophiles.

  卤化的二元酚（对苯二酚和间苯二酚）在超声处理下与nBuLi / TMEDA / THF或醚（反相添加）进行卤素金属交换，从而生成C，O，O-三锂化物质，可被亲电子试剂捕集。
• Antagonists for the Orphan G-Protein-Coupled Receptor GPR55 Based on a Coumarin Scaffold
  作者：Viktor Rempel、Nicole Volz、Franziska Gläser、Martin Nieger、Stefan Bräse、Christa E. Müller

  DOI：10.1021/jm4005175

  日期：2013.6.13

  The orphan G-protein-coupled receptor GPR55, which is activated by 1-lysophosphatidylinositol and interacts with cannabinoid (CB) receptor ligands, has been proposed as a new potential drug target for the treatment of diabetes, Parkinson's disease, neuropathic pain, and cancer. We applied beta-arrestin assays to identify 3-substituted coumarins as a novel class of antagonists and performed an extensive structure-activity relationship study for GPR55. Selectivity versus the related receptors CB1, CB2, and GPR18 was assessed. Among the 7-unsubstituted coumarins selective, competitive GPR55 antagonists were identified, such as 3-(2-hydroxybenzyl)-5-isopropyl-8-methyl-2H-chromen-2-one (12, PSB-SB-489, IC50 = 1.77 mu M, pA(2) = 0.547 mu M). Derivatives with long alkyl chains in position 7 were potent, possibly allosteric GPR55 antagonists which showed ancillary CB receptor affinity. 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one (69, PSB-SB-487, IC50 = 0.113 mu M, K-B = 0.561 mu M) and 7-(1,1-dimethylheptyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one (67, PSB-SB-1203, IC50 = 0.261 mu M) were the most potent GPR55 antagonists of the present series.
• Smith et al., Journal of Organic Chemistry, 1939, vol. 4, p. 340
  作者：Smith et al.

  DOI：——

  日期：——
• The Chemistry of Vitamin E. XXX. Condensation of Butadiene and of Crotyl Systems with Trimethylhydroquinone¹
  作者：Lee Irvin Smith、John A. King

  DOI：10.1021/ja01852a024

  日期：1941.7
• Mayer,H. et al., Helvetica Chimica Acta, 1963, vol. 46, p. 665 - 671
  作者：Mayer,H. et al.

  DOI：——

  日期：——