2-(3-hydroxypropyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione | 40740-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-hydroxypropyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,3,5-trimethyl-6-(3'-hydroxypropyl)-1,4-benzoquinone
• CAS: 40740-33-8
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: GDZGGXXBBFRGFE-UHFFFAOYSA-N

物化性质

• 沸点：
  334.0±21.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxypropyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 tert-butyl N-[(4S,5E,7S)-7-benzyl-8-[(2S)-2-{[(1S)-5-({[3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propoxy]carbonyl}amino)-1-[(propan-2-yl)carbamoyl]pentyl]carbamoyl}pyrrolidin-1-yl]-2-methyl-8-oxooct-5-en-4-yl]carbamate
  参考文献：
  名称：

  [EN] PREPARATION AND USES OF REACTIVE OXYGEN SPECIES SCAVENGER DERIVATIVES
  [FR] PRÉPARATION ET UTILISATIONS DE DÉRIVÉS PIÉGEURS D'ESPÈCES RÉACTIVES DE L'OXYGÈNE

  摘要：

  公式(I) a或(I) b的化合物：包括某些醌衍生物，以及相应的药物组合物，可以用于调节受试者中的铁死亡。本文还披露了这些化合物和药物组合物的制备方法，以及它们在制造药物中用于减少细胞中的活性氧化物（ROS）并预防、治疗、改善某些相关疾病或疾病的潜在用途。

  公开号：

  WO2019033330A1
• 作为产物：
  描述：

  6-hydroxy-5,7,8-trimethylchroman-2-one 在 lead(IV) acetate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3-hydroxypropyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Preparation of Hydroquinone Derivatives

  摘要：

  DOI：

  10.1246/bcsj.46.659

文献信息

• Synthesis of quinones having carboxy- and hydroxy-alkyl side chains, and their effects on rat-liver lysosomal membrane.
  作者：KAYOKO OKAMOTO、MASAZUMI WATANABE、MITSURU KAWADA、GIICHI GOTO、YASUKO ASHIDA、KATSUAKI ODA、AKIKO YAJIMA、ISUKE IMADA、HIROSHI MORIMOTO

  DOI：10.1248/cpb.30.2797

  日期：——

  In order to study the structure activity relationship of metabolites of ubiquinone, α-tocopherol and phylloquinone (Ia, b, c, IIa, b, c), 3-carboxy-2-butenyl (IIIa, b, c), 6-hydroxy-3-methyl-2-hexenyl (IVa, b, c), 4-hydroxy-3-methylbutyl (Va, b), 4-hydroxy-3-methyl-2-butenyl (VIb, c), ω-carboxyalkyl (VIIa, b, c), and ω-hydroxyalkyl (VIIIa, b) side chains were introduced into the 6-position of 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone and 2, 3, 5-trimethyl-1, 4-benzoquinone, as well as the 3-position of 2-methyl-1, 4-naphthoquinone. The effects of these quinones on the membrane stability of rat-liver lysosomes and on the activity of bovine heart phosphodiesterase were investigated. A good correlation was observed between these activities of the benzoquinone derivatives (VIIa, b).

  为了研究辅酶Q、α-生育酚和叶绿醌（Ia, b, c, IIa, b, c）的代谢产物结构活性关系，将3-羧基-2-丁烯基（IIIa, b, c）、6-羟基-3-甲基-2-己烯基（IVa, b, c）、4-羟基-3-甲基丁基（Va, b）、4-羟基-3-甲基-2-丁烯基（VIb, c）、ω-羧基烷基（VIIa, b, c）和ω-羟基烷基（VIIIa, b）侧链引入到2, 3-二甲氧基-5-甲基-1, 4-苯醌和2, 3, 5-三甲基-1, 4-苯醌的6-位以及2-甲基-1, 4-萘醌的3-位。研究了这些醌类化合物对大鼠肝脏溶酶体膜稳定性和牛心磷酸二酯酶活性的影响。苯醌衍生物（VIIa, b）的这些活性之间观察到了良好的相关性。
• Synthesis and Properties of Pheophorbide-Quinone Compounds
  作者：Victor V. Borovkov、Alexander A. Gribkov、Andrei N. Kozyrev、Alexander S. Brandis、Akito Ishida、Yoshiteru Sakata

  DOI：10.1246/bcsj.65.1533

  日期：1992.6

  New pheophorbide-quinone derivatives with a different kind of quinone moieties were synthesized by mixed anhydride method. The structures of these compounds were confirmed by UV, IR, 1H NMR, fluorescence, and mass spectra. Effective fluorescence quenching of the pheophorbide chromophores in the synthesized molecules was observed depending on the electron-accepting properties of the quinone fragment and spatial disposition of the donor and acceptor. Electron-transfer rate constants were calculated based on fluorescence decay measurements. The role of energetic and conformational changes of pheophorbide-quinones in the electron-transfer processes is discussed.

  通过混合酸酐法合成了具有不同醌基的新型叶绿素醌衍生物。通过紫外、红外、1H核磁共振、荧光和质谱对这些化合物的结构进行了确认。根据醌基的受电子性质以及供体和受体的空间分布，观察到了合成分子中叶绿素醌基的有效荧光猝灭。根据荧光衰减测量计算了电子转移速率常数。讨论了叶绿素醌在电子转移过程中的能量和构象变化的作用。
• Preparation and uses of reactive oxygen species scavenger derivatives
  申请人：XW LABORATORIES INC.

  公开号：US10858394B2

  公开（公告）日：2020-12-08

  Compounds of Formula (I)a or (I)b: including certain quinone derivatives, and the corresponding pharmaceutical compositions, which may serve to modulate ferroptosis in a subject. Also disclosed herein are the preparations of these compounds and pharmaceutical compositions and their potential uses in the manufacture of a medicament in reducing reactive oxygen species (ROS) in a cell and for preventing, treating, ameliorating certain related disorder or a disease.

  式 (I)a 或 (I)b 的化合物： 包括某些醌衍生物，以及相应的药物组合物，可用于调节受试者体内的铁变态反应。本文还公开了这些化合物和药物组合物的制备方法，以及它们在制造减少细胞中活性氧（ROS）和预防、治疗、改善某些相关失调或疾病的药物中的潜在用途。
• Riering, Helmut; Schaefer, Hans J., Chemische Berichte, 1994, vol. 127, # 5, p. 859 - 874
  作者：Riering, Helmut、Schaefer, Hans J.

  DOI：——

  日期：——
• Novel <i>ipso</i>-Substitution of <i>p</i>-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of <i>p</i>-Quinones and Protected <i>p</i>-Dihydroquinones
  作者：Shuji Akai、Yoshifumi Takeda、Kiyosei Iio、Kenji Takahashi、Nobuhisa Fukuda、Yasuyuki Kita

  DOI：10.1021/jo970418o

  日期：1997.8.1

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.