2,4-二氯-5-羟基苯甲醛 | 56962-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二氯-5-羟基苯甲醛
• 英文名称: 4,6-dichloro-3-hydroxybenzaldehyde
• 英文别名: 2,4-dichloro-5-hydroxy-benzaldehyde；2,4-Dichlor-5-hydroxy-benzaldehyd；2,4-Dichloro-5-hydroxybenzaldehyde
• CAS: 56962-15-3
• 化学式: C₇H₄Cl₂O₂
• 分子量: 191.014
• InChiKey: UGFNAHIFKWLQEV-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  280.8±35.0 °C(Predicted)
• 密度：
  1.547±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二氯-5-羟基苯甲醛 在 盐酸 作用下， 以 水 为溶剂， 生成 (RS)-4,6-dichloro-3-hydroxyphenylglycine
  参考文献：
  名称：

  Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

  摘要：

  1 We investigated the agonist and atagonist activities of 22 new phenylglycine and phenylalamine derivatives for metabotropic glutamate receptors (mGluRs) by examining their effects on the signal transduction of mGluR(1), mGluR(2) and mGluR(6) subtypes expressed in Chinese hamster ovary cells. This analysis revealed several structural characteristics that govern receptor subtype specificity of the agonist and antagonist activities of phenylglycine derivatives.2 Hydroxyphenylglycine derivatives possessed either an agonist activity on mGluR(1) mGluR(6) or an antagonist activity on mGluR(1).3 Carboxyphenylglycine derivatives showed an agonist activity on mGluR(2) but an antagonist activity on mGluR(1).4 alpha-Methylation or alpha-ethylation of the carboxyphenylglycine derivatives converts the agonist property For mGluR(2) to an antagonist property, thus producing antagonists at both mGluR(1) and mGluR(2).5 Structurally-corresponding phenylalanine derivatives showed little or no agonist or antagonist activity on any subtypes of the receptors.6 This investigation demonstrates that the nature and positions of side chains and ring substituents incorporated into the phenylglycine structure are critical in determining the agonist and antagonist activities of members of this group of compounds on different subtypes of the mGluR family.7 We also tested two alpha-methyl derivatives of mGluR agonists. (2S, 1'S, 2'S)-2-(2-Carboxycyciopropyl)glycine (L-CCG-I) is a potent agonist for mGluR(2) but alpha-methylation of this compound changes its activity to that of an mGluR(2)-selective antagonist. In contrast, alpha-methylation of L-2-amino-4-phosphonobutyrate (L-AP4) results in retention of an agonist activity on mCluR(6). Thus, alpha-methylation produces different effects, depending on the chemical structures of lead compounds and/or on the subtype of mGluR tested.

  DOI：

  10.1111/j.1476-5381.1996.tb15312.x
• 作为产物：
  描述：

  4-氯-3-甲基苯酚 在 氯 作用下， 生成 2,4-二氯-3-甲基苯酚 、 2,4-二氯-5-羟基苯甲醛
  参考文献：
  名称：

  Friedlaender; Schenck, Chemische Berichte, 1914, vol. 47, p. 3048

  摘要：

  DOI：

文献信息

• 1,4,4a,10b-Tetrahydro-<i>N,N</i>-dimethyl-4-phenanthridinamines and 1,4,4a,5,6,10b-hexahydro-<i>N,N</i>-dimethyl-4-phenanthridinamines
  作者：George Bobowski、Barbara West、Diana Omecinsky

  DOI：10.1002/jhet.5570290106

  日期：1992.1

  5-aryl-N,N-dimethyl-6-nitro-2-cyclohexen-1-amines 7. Reduction of 7 with zinc in acetic acid gave the diamino derivatives 8. Schotten-Baumann acylation of 8 gave amides 9. Treatment of 8 with alkyl isocyanates gave the aminourea derivatives 10. Bischler-Napieralski cyclodehydration procudure of 9 and 10 gave 1,4,4a,10b-tetrahydrophenanthridinamines 3 and N6-alkyl-1,4,4a,10b-tetrahydro-N4,N4-dimethyl-4

  描述了制备标题化合物的合成方法。将β-硝基苯乙烯衍生物5的Diels-Alder环加成到N，N-二甲基-1,3-丁二烯-1-胺6中，得到5-芳基-N，N-二甲基-6-硝基-2-环己烯-1-胺7.用锌在乙酸中还原7得二氨基衍生物8。Schotten-Baumann酰化8得到酰胺9。用烷基异氰酸酯处理8得到氨基脲衍生物10。的施勒-纳皮耶拉尔斯基环化脱水procudure 9和10，得到亚甲基-1,4,4a，10B-tetrahydrophenanthridinamines 3和N 6-烷基-1,4,4a，10b-四氢-N 4，N 4-二甲基-4,6-菲啶二胺11。在共沸条件下，二胺8与芳基醛的缩合得到亚胺12，该亚胺12在用酸处理时产生6-芳基-1,4,4a，5,6,10b-六氢-N，N-二甲基-4-菲啶胺4。这些材料的立体化学由质子磁共振研究确定。
• Hodgson; Beard, Journal of the Chemical Society, 1926, p. 154
  作者：Hodgson、Beard

  DOI：——

  日期：——
• Lock, Monatshefte fur Chemie, 1930, vol. 55, p. 307,311
  作者：Lock

  DOI：——

  日期：——
• Dr.F.Raschig G.m.b.H.
  作者：Dr.F.Raschig G.m.b.H.

  DOI：——

  日期：——
• Chlorination of 3-hydroxybenzaldehyde
  申请人：NAT ANILINE & CHEM CO INC

  公开号：US01776803A1

  公开（公告）日：1930-09-30