5,6-dihydroxy-1-tetralone | 59515-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,6-dihydroxy-1-tetralone
• 英文别名: 5,6-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 59515-92-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: KOTSTVOEHZEULD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dihydroxy-1-tetralone 在 甲醇 、 lithium aluminium tetrahydride 、 sodium azide 、 溴 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium iodide 作用下， 以 乙醚 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 37.75h， 生成 (1R,2R)-2-(benzyl(methyl)amino)-5,6-bis(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  [EN] BETA-2 SELECTIVE ADRENERGIC RECEPTOR AGONISTS
  [FR] AGONISTES DE RÉCEPTEUR ADRÉNERGIQUE BÊTA-2 SÉLECTIF

  摘要：

  公开号：

  WO2019112913A9
• 作为产物：
  描述：

  5,6-二甲氧基-1,2,3,4-四氢1-萘酮 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 5,6-dihydroxy-1-tetralone
  参考文献：
  名称：

  [EN] BETA-2 SELECTIVE ADRENERGIC RECEPTOR AGONISTS
  [FR] AGONISTES DE RÉCEPTEUR ADRÉNERGIQUE BÊTA-2 SÉLECTIF

  摘要：

  公开号：

  WO2019112913A9

文献信息

• Synthesis and biological activities of 3-aminomethyl-1,2-dihydronaphthalene derivatives.
  作者：KATSUMI ITOH、AKIO MIYAKE、MASAO TANABE、MINORU HIRATA、YOSHIKAZU OKA

  DOI：10.1248/cpb.31.2006

  日期：——

  A series of 3-aminomethyl-1, 2-dihydronaphthalene derivatives (6-22) was prepared from the corresponding 3, 4-dihydro-1 (2H)-naphthalenone derivatives (24a-q) in three steps, namely the Mannich reaction, reduction of the carbonyl group with sodium borohydride, and dehydration with ethanolic hydrogen chloride. Compounds 6-22 and several related analogs (23, 27-30) were tested for vasodilating and antihypertensive activities. Potent cerebral vasodilating and antihypertensive activities were exhibited by 1-benzhydryl-4-(7-disubstituted amino-1, 2-dihydro-3-naphthyl) methylpiperazines (16, 18 and 19).

  一系列3-氨基甲基-1,2-二氢萘衍生物（6-22）通过三步反应从相应的3,4-二氢-1(2H)-萘酚酮衍生物（24a-q）制备得到，这三步反应分别是曼尼希反应、用硼氢化钠还原羰基和用乙醇氢氯酸脱水。化合物6-22及其相关类似物（23, 27-30）被测试了血管舒张和抗高血压活性。1-二苯甲基-4-(7-二取代氨基-1,2-二氢-3-萘基)甲基哌嗪（16,18和19）展现了强大的脑部血管舒张和抗高血压活性。
• 1-aminomethyl-1,2,3,4-tetrahydronaphthalenes
  申请人：Abbott Laboratories

  公开号：US05128362A1

  公开（公告）日：1992-07-07

  The present invention provides compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sub.1 is selected from hydrogen, halo, lower alkyl, lower alkoxy, or thioalkoxy; and R.sub.2 is lower alkoxy; or R.sub.1 and R.sub.2 together form a methylenedioxy or ethylenedioxy ring; R.sub.3 and R.sub.4 are independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, (lower alkyl)amino, (lower alkylsulfonyl)amino, and halo; and R.sub.7 is selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, and ##STR2## where R.sub.13 and R.sub.14 are independently selected from the group consisting of hydrogen, hydroxy, halogen, amino, lower alkyl, lower alkoxy, lower alkylthio, methylenedioxy, or ethylenedioxy. The compounds of the present invention selectively inhibit .alpha..sub.2 -adrenergic receptors as well as inhibit the uptake of biogenic amines and are thus useful in the treatment of certain cardiovascular and psychiatric disorders.

  本发明提供了以下结构的化合物##STR1##或其药学上可接受的盐，其中R.sub.1从氢、卤素、较低的烷基、较低的烷氧基或硫代烷氧基中选择；而R.sub.2是较低的烷氧基；或者R.sub.1和R.sub.2一起形成一个亚甲二氧基或乙二氧基环；R.sub.3和R.sub.4独立地从氢、羟基、较低的烷基、较低的烷氧基、较低的烷硫基、(较低的烷基)氨基、(较低的烷基磺酰基)氨基和卤素中选择；而R.sub.7从2-或3-噻吩基、2-或3-呋喃基和##STR2##中选择，其中R.sub.13和R.sub.14独立地从氢、羟基、卤素、氨基、较低的烷基、较低的烷氧基、较低的烷硫基、亚甲二氧基或乙二氧基中选择。本发明的化合物选择性地抑制α2-肾上腺素受体，并抑制生物胺的摄取，因此在治疗某些心血管和精神疾病方面具有用处。
• A simple, high-yielding method for the methylenation of catechols
  作者：Robert E. Zelle、William J. McClellan

  DOI：10.1016/s0040-4039(00)74353-x

  日期：1991.11

  The methylenation of a variety of catechols is described, employing cesium carbonate and bromochloromethane in dimethylformamide t 110°C or acetonitrile at reflux. The corresponding methylenedioxy derivatives are obtained in 86-97 % yield. Utilization of this method provided β-hydrastine in 70% yield from its corresponding dihydroxy analog.

  描述了多种儿茶酚的亚甲基化，其使用碳酸铯和溴氯甲烷在110℃的二甲基甲酰胺或乙腈中回流。得到相应的亚甲二氧基衍生物，产率为86-97％。利用该方法，由其相应的二羟基类似物以70％的产率提供了β-水苏氨酸。
• Method for improving the absorption and effectiveness of a catecholamine compound
  申请人：SIMES S.p.A. Società Italiana Medicinali e Sintetici

  公开号：EP0167204A1

  公开（公告）日：1986-01-08

  New mono O-phosphate ester derivatives of catecholamine compounds are disclosed, which exhibit improved absorption and effectiveness with respect to their parent compounds.

  本研究公开了儿茶酚胺化合物的新单 O-磷酸酯衍生物，与母体化合物相比，这些衍生物的吸收性和有效性都有所提高。
• Synthesis and Reactivity of the Catechol Metabolites from the Equine Estrogen, 8,9-Dehydroestrone
  作者：Fagen Zhang、Dan Yao、Yousheng Hua、Richard B. van Breemen、Judy L. Bolton

  DOI：10.1021/tx010049y

  日期：2001.6.1

  The risk factors for women developing breast and endometrial cancers are all associated with a lifetime of estrogen exposure. Estrogen replacement therapy in particular has been correlated with an increased cancer risk. Previously, we showed that the equine estrogens equilin and equilenin, which are major components of the widely prescribed estrogen replacement formulation Premarin, are metabolized to highly cytotoxic quinoids which caused oxidative stress and alkylation of DNA in vitro [Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. Chem. Res. Toxicol. 1998, 11, 1113-1127]. In this study, we have synthesized 8,9-dehydroestrone (a third equine estrogen component of Premarin) and its potential catechol metabolites, 4-hydroxy-8,9-dehydroestrone and 2-hydroxy-8,9-dehydroestrone. Both 2-hydroxy-8,9-dehydroestrone and 4-hydroxy-8,9-dehydroestrone were oxidized by tyrosinase or rat liver microsomes to o-quinones which reacted with GSH to give one mono-GSH conjugate and two di-GSH conjugates. Like endogenous estrogens, 8,9-dehydroestrone was primarily converted by rat liver microsomes to the 2-hydroxylated rather than the 4-hydroxylated o-quinone GSH conjugates; the ratio of 2-hydroxy-8,9-dehydroestrone versus 4-hydroxy-8,9-dehydroestrone was 6:1. Also in contrast to experiments with equilin, 4-hydroxyequilenin was not observed in microsomal incubations with 8,9-dehydroestrone or its catechols. The behavior of 2-hydroxy-8,9-dehydroestrone was found to be more complex than 4-hydroxy-8,9-dehydroestrone as GSH conjugates resulting from 2-hydroxy-8,9-dehydroestrone were detected even without oxidative enzyme catalysis. Under physiological conditions, 2-hydroxy-8,9-dehydroestrone isomerized to 8-hydroxyequilenin to form the very stable 2-hydroxyequilenin catechol; however, 4-hydroxy-8,9-dehydroestrone was found to be stable under similar conditions. Finally, preliminary studies conducted with the human breast tumor S-30 cell lines demonstrated that the catechol metabolites of 8,9-dehydroestrone were much less toxic than 4-hydroxyequilenin (20-40-fold). These results suggest that the catechol metabolites of 8,9-dehydroestrone may have the ability to cause cytotoxicity in vivo primarily through formation of o-quinones; however, most of the adverse effects of Premarin estrogens are likely due to formation of 4-hydroxyequilenin o-quinone from equilin and equilenin.