4-hydroxy-3-nitrobenzyl bromide | 177179-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-nitrobenzyl bromide
• 英文别名: 4-bromomethyl-2-nitro-phenol；4-Brommethyl-2-nitro-phenol；ω-Brom-3-nitro-4-oxy-toluol；3-Nitro-4-oxy-benzylbromid；1¹-Brom-3-nitro-4-oxy-1-methyl-benzol；4¹-Brom-2-nitro-p-kresol；4-(Bromomethyl)-2-nitrophenol
• CAS: 177179-94-1
• 化学式: C₇H₆BrNO₃
• 分子量: 232.034
• InChiKey: ZIQMMTGKQQKNSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-nitrobenzyl bromide 在 盐酸 、 N,O-双三甲硅基乙酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 [(3S)-3-amino-3-carboxypropyl][(4-hydroxy-3-nitrophenyl)methyl]phosphinic acid
  参考文献：
  名称：

  Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.7b01438
• 作为产物：
  描述：

  4-羟基-3-硝基苄醇 在 氢溴酸 、 苯 作用下， 生成 4-hydroxy-3-nitrobenzyl bromide
  参考文献：
  名称：

  Shoesmith; Hetherington; Slater, Journal of the Chemical Society, 1924, vol. 125, p. 1315

  摘要：

  DOI：

文献信息

• [EN] DIASTEREOISOMERS OF HYPOPHOSPHOROUS ACID DERIVATIVES<br/>[FR] DIASTÉRÉOISOMÈRES DE DÉRIVÉS D'ACIDE HYPOPHOSPHOREUX
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2010106526A1

  公开（公告）日：2010-09-23

  The invention relates to the diastereoisomers of hypophosphorous acid derivatives, having formula (I), wherein the phenyl group is substituted by one or several atoms or groups, occupying one or several positions on the phenyl ring, and a method for the separation thereof.

  该发明涉及具有式（I）的次磷酸衍生物的对映异构体，其中苯基被一个或多个原子或基团取代，占据苯环上的一个或多个位置，并提供了一种分离它们的方法。
• Shoesmith; Hetherington; Slater, Journal of the Chemical Society, 1924, vol. 125, p. 1315
  作者：Shoesmith、Hetherington、Slater

  DOI：——

  日期：——
• Stoermer; Behn, Chemische Berichte, 1901, vol. 34, p. 2459
  作者：Stoermer、Behn

  DOI：——

  日期：——
• Auwers, Chemische Berichte, 1906, vol. 39, p. 3174
  作者：Auwers

  DOI：——

  日期：——
• DE132475
  申请人：——

  公开号：——

  公开（公告）日：——