3,6-dihydroxyphenanthrene | 30309-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3,6-dihydroxyphenanthrene
• 英文别名: 3,6-dihydroxynaphthalene；3.6-Dihydroxy-phenanthren；phenanthrene-3,6-diol；Phenanthren-3,6-diol；3,6-Phenanthrenediol
• CAS: 30309-92-3
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: KETVJOBTVPUWMG-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C
• 沸点：
  475.0±18.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3,6-dihydroxyphenanthrene 在 铬酸 、 溶剂黄146 作用下， 生成 3,6-dimethoxy-9,10-phenanthrenequinone
  参考文献：
  名称：

  Fieser, Journal of the American Chemical Society, 1929, vol. 51, p. 2468

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二甲氧基芪 在 碘 、 三溴化硼 、 methyloxirane 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 96.0h， 生成 3,6-dihydroxyphenanthrene
  参考文献：
  名称：

  Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

  摘要：

  Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.05.074

文献信息

• Synthesis of <i>o</i>-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone
  作者：Keshaba Nanda Parida、Jarugu Narasimha Moorthy

  DOI：10.1021/acs.joc.5b00292

  日期：2015.8.21

  A simple procedure for the synthesis of a variety of o-carboxyarylacrylic acids has been developed with Oxone (2KHSO5·KHSO4·K2SO4); the oxidation reaction involves the stirring of methoxy/hydroxy-substituted naphthalenes, phenanthrenes, anthracenes, etc. with Oxone in an acetonitrile–water mixture (1:1, v/v) at rt. Mechanistically, the reaction proceeds via initial oxidation of naphthalene to o-quinone

  已经用Oxone（2KHSO 5 ·KHSO 4 ·K 2 SO 4）开发了一种简单的合成多种邻-羧基芳基丙烯酸的方法。氧化反应包括在室温下将乙氧基/羟基取代的萘，菲，蒽等与Oxone在乙腈-水混合物（1：1，v / v）中搅拌。从机理上讲，该反应是通过将萘初始氧化为邻醌而进行的，该邻苯醌会裂解成相应的邻羧基芳基丙烯酸。发现高级芳族化合物产生衍生自最初形成的邻-羧基芳基丙烯酸的羧甲基内酯。
• Method of preventing polymer-scale formation
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0320227B1

  公开（公告）日：1994-09-07
• Composition for film formation and insulating film
  申请人：JSR Corporation

  公开号：EP1122746B1

  公开（公告）日：2004-09-22
• SUBSTITUTED PHENETHYLAMINES WITH SEROTONINERGIC AND/OR NOREPINEPHRINERGIC ACTIVITY
  申请人：Auspex Pharmaceuticals, Inc.

  公开号：US20140296339A1

  公开（公告）日：2014-10-02

  Chemical syntheses and medical uses of novel inhibitors of the uptake of monoamine neurotransmitters and pharmaceutically acceptable salts and prodrugs thereof, for the treatment and/or management of psychotropic disorders, anxiety disorder, generalized anxiety disorder, depression, post-traumatic stress disorder, obsessive-compulsive disorder, panic disorder, hot flashes, senile dementia, migraine, hepatopulmonary syndrome, chronic pain, nociceptive pain, neuropathic pain, painful diabetic retinopathy, bipolar depression, obstructive sleep apnea, psychiatric disorders, premenstrual dysphoric disorder, social phobia, social anxiety disorder, urinary incontinence, anorexia, bulimia nervosa, obesity, ischemia, head injury, calcium overload in brain cells, drug dependence, and/or premature ejaculation are described.
• METHODS AND SYSTEMS OF GRAFT POLYMERIZATION ON A FUNCTIONALIZED SUBSTRATE
  申请人：Spevacek John A.

  公开号：US20140296366A1

  公开（公告）日：2014-10-02

  Graft polymerization is fullfiled on a functionalized substrate. The functionalized substrate is prepared from a disulfide bond-containing feedstock and has been prepared for polymerization through the introduction of one or more polyfunctional monomers containing a disulfide bond breaking material functional group.