2-hydroxy-5-methoxy-3,4,6-trimethylbenzaldehyde | 607351-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-methoxy-3,4,6-trimethylbenzaldehyde
• CAS: 607351-63-3
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: TVLALPLXLPFGEN-UHFFFAOYSA-N

物化性质

• 沸点：
  308.5±37.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-hydroxy-5-methoxy-3,4,6-trimethylbenzaldehyde 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以62%的产率得到4-methoxy-3,4,6-trimethylbenzene-1,2-diol
  参考文献：
  名称：

  Development of Novel Antioxidants:  Design, Synthesis, and Reactivity

  摘要：

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.

  DOI：

  10.1021/jo0301090
• 作为产物：
  描述：

  三甲基氢醌 在 咪唑 、 三正丁胺 、 四丁基氟化铵 、 四氯化锡 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 27.0h， 生成 2-hydroxy-5-methoxy-3,4,6-trimethylbenzaldehyde
  参考文献：
  名称：

  Development of Novel Antioxidants:  Design, Synthesis, and Reactivity

  摘要：

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.

  DOI：

  10.1021/jo0301090

文献信息

• Regioselective and Enantioselective Domino Aldol-Oxa-Michael Reactions to Construct Quaternary (Chroman) Stereocenters
  作者：Kegang Liu、Xiaohua Jiang

  DOI：10.1002/ejoc.201501065

  日期：2015.9

  An asymmetric domino aldol–oxa-Michael reaction of salicylaldehydes and β,β-disubstituted α,β-unsaturated aldehydes has been developed by using dienamine-mediated catalysis. The developed strategy leading to the stereoselective and regioselective formation of novel chroman derivatives with quaternary (chroman) stereocenters is presented. Particularly, salicylaldehydes with variously substitution patterns

  通过使用二烯胺介导的催化，开发了水杨醛和 β,β-二取代 α,β-不饱和醛的不对称多米诺羟醛-氧杂-迈克尔反应。介绍了导致具有四元（色满）立体中心的新型色满衍生物的立体选择性和区域选择性形成的已开发策略。特别是，具有不同取代模式的水杨醛主导了具有高分子复杂性和骨架多样性的色满衍生物的有效构建，具有优异的非对映选择性和对映选择性。
• 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.
• Asymmetric Synthesis of α-Tocopherol
  作者：Urs Hengartner、Antoinette Chougnet、Kegang Liu、Wolf-D. Woggon

  DOI：10.1002/chem.200902754

  日期：2010.1.25

  Abstractα‐Tocopherol was synthesized from a chiral intermediate α‐hydroxy ester by means of two ring‐closing methods to yield the chromanol in 94 % diastereomeric excess.
• Smith et al., Journal of Organic Chemistry, 1939, vol. 4, p. 340
  作者：Smith et al.

  DOI：——

  日期：——
• A Short Route to α‐Tocopherol
  作者：Kegang Liu、Antoinette Chougnet、Wolf‐D. Woggon

  DOI：10.1002/anie.200801765

  日期：2008.7.21