1-(3,4-dihydroxy-2-nitrophenyl)-1-phenylmethanone | 383382-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dihydroxy-2-nitrophenyl)-1-phenylmethanone
• 英文别名: BIA 8-176；3,4-dihydroxy-2-nitrobenzophenone；(3,4-dihydroxy-2-nitro-phenyl)-phenyl-methanone；(3,4-dihydroxy-2-nitrophenyl)phenylmethanone；(3,4-Dihydroxy-2-nitrophenyl)(phenyl)methanone；(3,4-dihydroxy-2-nitrophenyl)-phenylmethanone
• CAS: 383382-84-1
• 化学式: C₁₃H₉NO₅
• 分子量: 259.218
• InChiKey: ICLKAUQIPVFHOI-UHFFFAOYSA-N

物化性质

• 沸点：
  490.7±45.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-dihydroxy-2-nitrophenyl)-1-phenylmethanone 、 丁酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-哌啶羧酸,1-甲基-,2-(氨基硫代甲基)酰肼
  参考文献：
  名称：

  Substituted nitrated catechols, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them

  摘要：

  公式I的新化合物被描述如下： 这些化合物在治疗一些中枢和外周神经系统疾病中具有潜在的有价值的药理特性。

  公开号：

  EP1167341A1
• 作为产物：
  描述：

  1-(4-acetyloxy-3-methoxy-2-nitrophenyl)-1-phenylmethanone 在 吡啶 、 sodium hydroxide 、 三氯化铝 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 0.75h， 生成 1-(3,4-dihydroxy-2-nitrophenyl)-1-phenylmethanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of “Ortho-Nitrated” Inhibitors of Catechol-O-methyltransferase

  摘要：

  Novel regioisomeric "ortho-nitrated" catechols related to the catechol-O-methyltransferase (COMT) inhibitors BIA 3-202 3 and BIA 3-335 4 were synthesized and biologically evaluated. Changing the position of the nitro group from the "classical" meta- to the ortho-position relative to the side-chain substituent of the nitrocatechol pharmacophore exerted profound effects on selectivity and duration of COMT inhibition. Alkylaryl compounds 7a-d possessed shorter duration of action than their regioisomers, but 7b displayed reversed selectivity over 3 at 3 and 6 h, exhibiting preferential central inhibition. In the amino-substituted series, ortho-nitrated regioisomer 14k was less peripherally selective than 4 and short-acting, whereas decahydroquinoline 14g displayed an unprecedented combination of long-acting and selective peripheral inhibition. 7b could provide a useful tool to probe the pharmacological utility of short-acting, centrally selective COMT inhibitors in the treatment of depression in Parkinsonian patients, and 14g represents a promising candidate for clinical evaluation as an adjunct to L-Dopa therapy.

  DOI：

  10.1021/jm0580454

文献信息

• Method for the nitration of phenolic compounds
  申请人：——

  公开号：US20040192961A1

  公开（公告）日：2004-09-30

  A method for the regioselective ortho-directed nitration of phenolic compounds useful for the preparation of ortho-nitro-phenols according to formula (I) is described. 1

  本文描述了一种用于苯酚化合物的区域选择性正向取向硝化的方法，可用于制备公式（I）中的正向硝基苯酚。
• METHOD FOR THE NITRATION OF PHENOLIC COMPOUNDS
  申请人：Portela & CA SA

  公开号：EP1409446A1

  公开（公告）日：2004-04-21
• US7005553B2
  申请人：——

  公开号：US7005553B2

  公开（公告）日：2006-02-28
• [EN] SUBSTITUTED NITRATED CATECHOLS, THEIR USE IN THE TREATMENT OF SOME CENTRAL AND PERIPHERAL NERVOUS SYSTEM DISORDERS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] CATECHINES NITREES SUBSTITUEES, LEUR UTILISATION DANS LE TRAITEMENT D'AFFECTIONS DU SYSTEME NERVEUX CENTRAL ET PERIPHERIQUE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：PORTELA & CA SA

  公开号：WO2001098250A1

  公开（公告）日：2001-12-27

  New compounds of formula (I) are described. The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders.
• [EN] METHOD FOR THE NITRATION OF PHENOLIC COMPOUNDS<br/>[FR] PROCEDE DE NITRATION DE COMPOSES PHENOLIQUES
  申请人：PORTELA & CA SA

  公开号：WO2003011810A1

  公开（公告）日：2003-02-13

  A method for the regioselective ortho-directed nitration of phenolic compounds useful for the preparation of ortho-nitro-phenols according to formula (I) is described.