6-allyl-2,3-dimethylbenzene-1,4-diol | 66557-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-allyl-2,3-dimethylbenzene-1,4-diol
• 英文别名: 2-allyl-5,6-dimethylhydroquinone；5-allyl-2,3-dimethylhydroquinone；5-Allyl-2,3-dimethyl-hydrochinon；5,6-Dimethyl-2-allylhydrochinon；5-Allyl-2,3-dimethylhydrochinon；5-Allyl-2,3-dimethyl-1,4-benzenediol；2,3-dimethyl-5-prop-2-enylbenzene-1,4-diol
• CAS: 66557-15-1
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: VZFYJEMQJBDZAV-UHFFFAOYSA-N

物化性质

• 沸点：
  326.8±37.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-allyl-2,3-dimethylbenzene-1,4-diol 在 三正丁胺 、 四氯化锡 、 对甲苯磺酸 作用下， 以 甲苯 、 苯 为溶剂， 反应 10.0h， 生成 5-hydroxy-2,6,7-trimethyl-2,3-dihydrobenzofuran-4-carbaldehyde
  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：

  2,3-二甲基氢醌 在 potassium carbonate 作用下， 以 丙酮 、 萘烷 为溶剂， 反应 23.0h， 生成 6-allyl-2,3-dimethylbenzene-1,4-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

文献信息

• 929. Chrom-3-en-6-ols. The action of pyridine on alk-2-enyl-benzoquinones
  作者：D. McHale、J. Green

  DOI：10.1039/jr9650005060

  日期：——
• Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilane
  作者：J.S Yadav、B.V.S Reddy、T Swamy

  DOI：10.1016/s0040-4039(03)01130-4

  日期：2003.6

  p-Quinones react smoothly with allyltrimethylsilane in the presence of 2 mol%, of Bi(OTf)(3) under mild reaction conditions to afford the corresponding allyl substituted benzene derivatives, p-allylquinols and allyl substituted 1,4-naphthoquinones in excellent yields with high regioselectivity. This method is very useful for the direct introduction of an allyl functionality onto a quinone moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Allylation of quinones with allyltin reagents
  作者：Yoshinori Naruta

  DOI：10.1021/ja00531a019

  日期：1980.5
• UBIQUINONE-1
  作者：Naruta, Yoshinori、Maruyama, Kazuhiro

  DOI：10.15227/orgsyn.071.0125

  日期：——
• Synthesis of a New type of Antioxidant possessing Inhibitory Activity against HMG-CoA Reductase
  作者：Masakatsu Matsumoto、Nobuko Watanabe、Eiko Mori、Misao Aoyama、Jun Kusunoki、Tetsuaki Yamaura

  DOI：10.3987/com-94-6908

  日期：——

  The 6-hydroxychromans (4) and (6), and 5-hydroxy-2,3-dihydrobenzo[b]furans (5) and (7) bearing a 4-hydroxypyran-2-one moiety were synthesized. All the compounds exhibited potent activity against lipid peroxidation. The chroman (4) possessed inhibitory activity against HMG-CoA reductase in addition to the antioxidant character.