3-羟基-2-甲基丙-2-烯醛 | 57325-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-2-甲基丙-2-烯醛
• 英文名称: methylmalonaldehyde enol tautomer
• 英文别名: 3-hydroxy-2-methyl-propenal；3-hydroxy-2-methyl-acrylaldehyde；3-Hydroxy-2-methyl-acrylaldehyd；2-Propenal, 3-hydroxy-2-methyl-；3-hydroxy-2-methylprop-2-enal
• CAS: 57325-58-3
• 化学式: C₄H₆O₂
• 分子量: 86.0904
• InChiKey: GJYMRMWAVJYYEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3-羟基-2-甲基丙-2-烯醛 、 4-溴苯甲脒盐酸盐水合物 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-(4-溴苯基)-5-甲基嘧啶
  参考文献：
  名称：

  Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines

  摘要：

  5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20 and c.200 nM, respectively, measured as 50% inhibition of the binding of 1-(-4-ethynylphenyl)-4-[H-3]propyl-2,6,7-trioxabicyclo[2.22]octane (4'-ethynyl-4-n-[H-3]propylbicycloorthobenzoate; [H-3]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated dies with LD(50) values of 6-27 mu g g(-1) alone and 2-6 mu g g(-1) with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl > isopropyl approximate to cyclohexyl approximate to cyclopropyl > methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl much greater than 4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [H-3]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.

  DOI：

  10.1002/(sici)1096-9063(199603)46:3<237::aid-ps359>3.0.co;2-p
• 作为产物：
  描述：

  丙醛二乙基乙缩醛 、 N,N-二甲基甲酰胺 生成 3-羟基-2-甲基丙-2-烯醛
  参考文献：
  名称：

  鸟嘌呤的荧光修饰。与取代的丙二醛反应。

  摘要：

  DOI：

  10.1021/jo00864a023

文献信息

• Degenerative chemistry of malondialdehyde. Structure, stereochemistry, and kinetics of formation of enaminals from reaction with amino acids
  作者：Vasu Nair、David E. Vietti、Curt S. Cooper

  DOI：10.1021/ja00401a020

  日期：1981.6
• Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines
  作者：David A. Pulman、Ian H. Smith、John P. Larkin、John E. Casida

  DOI：10.1002/(sici)1096-9063(199603)46:3<237::aid-ps359>3.0.co;2-p

  日期：1996.3

  5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20 and c.200 nM, respectively, measured as 50% inhibition of the binding of 1-(-4-ethynylphenyl)-4-[H-3]propyl-2,6,7-trioxabicyclo[2.22]octane (4'-ethynyl-4-n-[H-3]propylbicycloorthobenzoate; [H-3]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated dies with LD(50) values of 6-27 mu g g(-1) alone and 2-6 mu g g(-1) with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl > isopropyl approximate to cyclohexyl approximate to cyclopropyl > methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl much greater than 4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [H-3]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.
• Fluorescent modification of guanine. Reaction with substituted malondialdehydes
  作者：Robert C. Moschel、Nelson J. Leonard

  DOI：10.1021/jo00864a023

  日期：1976.1