6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one | 19017-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one
• 英文别名: 6-Hydroxy-2,2,5,7,8-pentamethyl-chroman-4-one；6-hydroxy-2,2,5,7,8-pentamethyl-3H-chromen-4-one
• CAS: 19017-66-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ZTLCFIJBECJUHW-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  399.4±42.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one 在 盐酸 、 甲醇 、 amalgamated zinc 作用下， 生成 3,4-二氢-2,2,5,7,8-五甲基-2H-1-苯并吡喃-6-酚
  参考文献：
  名称：

  John et al., Chemische Berichte, 1938, vol. 71, p. 2637,2647

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,6-trimethylhydroquinone bis(3,3-dimethylacrylate) 在 aluminum (III) chloride 、 盐酸 、 甲醇 、 sodium hydroxide 、 水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one
  参考文献：
  名称：

  Chroman derivatives as lipoxygenase inhibitors

  摘要：

  本发明涉及Formula I的某些新颖衍生物：其中X和R1至R10如规范中所述，其中R5为OH，—NRdORa或—NRd—NRbRc之一，或R7为—NRdORa或—NRd—NRbRc之一，或C═R7R8为C═NORa或C═N—NRbRc，这些可能在制造用于治疗通过脂氧合酶介导的疾病的药物组合物中有用。它们还可能在制造用于治疗脂氧合酶介导疾病的皮肤护理和/或药用组合物中有用。

  公开号：

  US20060193797A1

文献信息

• From a Theoretical Concept to Biochemical Reactions: Strain-Induced Bond Localization (SIBL) in Oxidation of Vitamin E
  作者：Thomas Rosenau、Gerald Ebner、Amnon Stanger、Sharon Perl、Limor Nuri

  DOI：10.1002/chem.200400265

  日期：2005.1

  from five- to six- and seven-membered rings, as predicted by the Mills-Nixon effect. The relative amounts of the products were determined at four different temperatures, and assuming that the product ratio represents the relative rates ratio, the relative enthalpy of activations could be obtained. Theoretically (at B3LYP/6-31G* theoretical level) four different intermediates were considered. Each of these

  α-生育酚（维生素E的主要成分）氧化为邻醌甲基化物（oQM）的区域选择性在文献中主要通过定义不明确的术语“米尔斯-尼克森效应”进行了解释。在本文中，我们描述了11种α-生育酚衍生物的制备方法，它们的相变角之和互不相同，但保持电子因子不变。这些化合物经历了Ag（2）O氧化，形成两个异构的oQM，它们被乙烯基甲基醚捕获。已经发现，异构体产物比率随环角的变化而平滑地变化，而不是如由米尔斯-尼克森效应所预测的那样，在从五元环到六元环和七元环的情况下，一个区域异构体到另一个区域异构体突然变化。产品的相对含量是在四个不同的温度下确定的，并假设乘积比代表相对速率比，则可以获得相对活化的焓。从理论上（在B3LYP / 6-31G *理论水平上）考虑了四种不同的中间体。这些中的每一个都经历了角形变以对两个区域异构体建模。在每个变形角处，两个中间体模型之间的能量差与四个中间体中每个中间体的实验数据相关。发现角
• Derivatives of 2,3-dihydro benzofuranols
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05721233A1

  公开（公告）日：1998-02-24

  Derivatives of 2,3-dihydro-5-benzofuranol, intermediates thereof, and processes useful for their preparation. These compounds are free radical scavengers and are useful in the treatment of conditions capable of being treated by free radical scavengers, such as stroke, nervous system trauma and reperfusion damage.

  2,3-二氢-5-苯并呋喃醇的衍生物，其中间体以及用于它们制备的有用过程。这些化合物是自由基清除剂，在治疗能够通过自由基清除剂治疗的疾病，如中风、神经系统创伤和再灌注损伤方面具有用处。
• [EN] NOVEL USE OF SUBSTITUTED 2H-CHROMENS AND THEIR DERIVATIVES<br/>[FR] NOUVELLE UTILISATION DES 2H-CHROMÈNES SUBSTITUÉS ET DE LEURS DÉRIVÉS
  申请人：DSM IP ASSETS BV

  公开号：WO2019185898A1

  公开（公告）日：2019-10-03

  The present invention is directed towards the use of 2H-chromens and their derivatives of formula (I) and/or of formula (II) wherein R1 and R2 are independently from each other H or C1-11-alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1 and R2 together represent a keto group, and wherein R3, R4, R5, and R6 are independently from each other H or C1-6-alkyl or C1-6-alkoxy, and R7 is H or C1-6-alkyl, as antioxidants, especially in feed such as pet food and feed ingredients such as fish meal, insect meal and poultry meal, as well as PUFA-containing oil such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil. The present invention is further directed towards feed ingredients and feed for insects, aquatic and terrestrial animals comprising such 2H- chromens and their derivatives of formula (I) and/or of formula (II).

  本发明涉及使用2H-香豆素及其衍生物的公式(I)和/或公式(II)，其中R1和R2分别独立于H或C1-11-烷基或(CH2)n— OH，其中n为1至6之间的整数，或者R1和R2一起代表一个酮基，且其中R3、R4、R5和R6分别独立于H或C1-6-烷基或C1-6-烷氧基，R7为H或C1-6-烷基，作为抗氧化剂，特别是在饲料中，如宠物食品和饲料成分，如鱼粉、昆虫粉和禽畜粉，以及PUFA含量较高的油，如海洋油、微生物油、真菌油、藻类油和富含PUFA的植物油。本发明还涉及含有这些2H-香豆素及其衍生物的公式(I)和/或公式(II)的饲料成分和饲料，用于昆虫、水生动物和陆生动物。
• 5,7,8-Trimethyl-benzopyran and 5,7,8-Trimethyl-1,4-benzoxazine Aminoamide Derivatives as Novel Antiarrhythmics against Ischemia−Reperfusion Injury
  作者：Eftychia N. Koini、Panagiota Papazafiri、Athanasios Vassilopoulos、Maria Koufaki、Zoltán Horváth、István Koncz、László Virág、Gy J. Papp、Andràs Varró、Theodora Calogeropoulou

  DOI：10.1021/jm801228h

  日期：2009.4.23

  6-Hydroxy-5,7,8-trimethyl-benzopyran derivatives and 5,7,8-trimethyl-1,4-benzoxazine analogues substituted by the lidocaine pharmacophore aminoamide functionality at C4 of N4, respectively, were synthesized and evaluated against arrhythmias associated with ischemia-reperfusion injury. The antiarrhythmic effect of substitutents at positions C2 and C6 was examined. Six out of the 11 new derivatives, exhibited arrhythmia scores 1.0-1.3 versus the control (4.5 +/- 1.2), which was also reflected to the % premature beats (0.5-3.9), control (13.7 +/- 3.6). Selected compounds were further studied by a conventional microelectrode method. 2-diethylamino-1-(5,7,8-trimethyl-2-phenyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethanotic (50) and the trolox-inspired 4-(2-diethylamino-acetyl)-2,5,7,8-tetramethyl-3.4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (62) Suppress reperfusion arrhythmias and reduce malondialdehyde (MDA) content, leading to a fast recovery of the heart after ischemia-reperfusion. They exhibit combined class IB and class III antiarrhythmic properties, which constitutes them as promising compounds for further studies because, due to their multichannel "amiodarone like" effect, less proarrhythmic complications can be expected.
• Offe; Barkow, Chemische Berichte, 1947, vol. 80, p. 464,467
  作者：Offe、Barkow

  DOI：——

  日期：——