5-nitrovanillic alcohol | 37987-22-7

• 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: 5-nitrovanillic alcohol
• 英文别名: 4-hydroxy-5-methoxy-3-nitrobenzyl alcohol；4-(hydroxymethyl)-2-methoxy-6-nitrophenol；5-Nitrovanillylalkohol；4-hydroxy-3-methoxy-5-nitro-benzyl alcohol；4-Hydroxy-3-methoxy-5-nitro-benzylalkohol
• CAS: 37987-22-7
• 化学式: C₈H₉NO₅
• 分子量: 199.163
• InChiKey: UHBLHKULNVLPSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitrovanillic alcohol 在 硫酸 、 硝酸 、 亚硝酸 作用下， 生成 6-甲氧基-2,4-二硝基苯酚
  参考文献：
  名称：

  Bazanova, G. V.; Stotskii, A. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 10, p. 1845 - 1850

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 乙醚 、 亚硝酸 、 丙酮 作用下， 生成 5-nitrovanillic alcohol
  参考文献：
  名称：

  Andersen, 1956, vol. 19, # 1, p. 23

  摘要：

  DOI：

文献信息

• Annulation-Induced Cascade Transformation of 5-Iodo-1,2,3-triazoles to 2-(1-Aminoalkyl)benzoxazoles
  作者：Yury N. Kotovshchikov、Gennadij V. Latyshev、Mger A. Navasardyan、Dmitry A. Erzunov、Irina P. Beletskaya、Nikolay V. Lukashev

  DOI：10.1021/acs.orglett.8b01755

  日期：2018.8.3

  Base-mediated cyclization of (5-iodo-1,2,3-triazolyl)phenols was proposed as a new synthetic strategy for the in situ generation of diazoimines via electrocyclic ring opening of the fused heterocycle. Cu-catalyzed amination of the intermediate diazoalkanes was employed to develop an efficient cascade approach to functionalized benzoxazoles.

  （5-碘-1,2,3-三唑基）苯酚的碱介导环化被提出为通过稠合杂环的电环开环原位产生重氮亚胺的新合成策略。铜催化的中间体重氮烷的胺化反应被用于开发一种有效的级联方法来官能化苯并恶唑。
• Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites
  作者：Chelliah Selvam、Isabelle A. Lemasson、Isabelle Brabet、Nadia Oueslati、Berin Karaman、Alexandre Cabaye、Amélie S. Tora、Bruno Commare、Tiphanie Courtiol、Sara Cesarini、Isabelle McCort-Tranchepain、Delphine Rigault、Laetitia Mony、Thomas Bessiron、Heather McLean、Frédéric R. Leroux、Françoise Colobert、Hervé Daniel、Anne Goupil-Lamy、Hugues-Olivier Bertrand、Cyril Goudet、Jean-Philippe Pin、Francine C. Acher

  DOI：10.1021/acs.jmedchem.7b01438

  日期：2018.3.8

  A group III metabotropic glutamate (mGlu) receptor agonist (PCEP) was identified by virtual HTS. This orthosteric ligand is composed by an L-AP4-derived fragment that mimics glutamate and a chain that binds into a neighboring pocket, offering possibilities to improve affinity and selectivity. Herein we describe a series of derivatives where the distal chain is replaced by an aromatic or heteroaromatic group. Potent agonists were identified, including some with a mGlu(4) subtype preference, e.g., 17m (LSP1-2111) and 16g (LSP4-2022). Molecular modeling suggests that aromatic functional groups may bind at either one of the two chloride regulatory sites. These agonists may thus be considered as particular bitopic/dualsteric ligands. 17m was shown to reduce GABAergic synaptic transmission at striatopallidal synapses. We now demonstrate its inhibitory effect at glutamatergic parallel fiber-Purkinje cell synapses in the cerebellar cortex. Although these ligands have physicochemical properties that are markedly different from typical CNS drugs, they hold significant therapeutic potential.
• Darstellung und Oxydation von Hydroxybenzylalkoholen
  作者：P. Claus、P. Schilling、J. S. Gratzl、K. Kratzl

  DOI：10.1007/bf00905194

  日期：——
• Andersen, 1956, vol. 19, # 1, p. 37
  作者：Andersen

  DOI：——

  日期：——