2-Acetonyl-4-(p-chlorophenyl)-2-hydroxybutanoic Acid | 111751-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-Acetonyl-4-(p-chlorophenyl)-2-hydroxybutanoic Acid
• 英文别名: 2-[2-(4-Chlorophenyl)ethyl]-2-hydroxy-4-oxopentanoic acid
• CAS: 111751-11-2
• 化学式: C₁₃H₁₅ClO₄
• 分子量: 270.713
• InChiKey: HTNCSUAQHGEBHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Acetonyl-4-(p-chlorophenyl)-2-hydroxybutanoic Acid 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以80%的产率得到3-[2-(4-chlorophenyl)ethyl]-5-hydroxy-5-methyl-2(5H)-furanone
  参考文献：
  名称：

  Dehydration of 2-(2-Arylethyl)-2-hydroxy-4-oxopentanoic Acids and their hydrazones to form heterocycles

  摘要：

  Dehydration of 2-(2-arylethyl)-2-hydroxy-4-oxopentanoic acids 1 with hydrochloric acid/acetic acid, affords 3-(2-arylethyl)-5-hydroxy-5-methyl-2(5H)-furanones 4. Compounds of type 1 and 4 represent suitable precursors for the formation of pyridazin-3-ones 7 as they smoothly react with hydrazine. A new series of s-triazolo[4,3-b]pyridazin-3-ones 12 and tetrazolo[1,5-b]pyridazines 15 are obtained from the 3-chloropyridazines 11 upon treatment with semicarbazide and sodium azide, respectively. Reaction of 11 with phenyl- acetyl-hydrazine provides 3-benzyl-6-phenyl-8-(2-phenyl-ethyl)-s-triazolo [4,3-b]pyridazine 13 via dehydrative cyclization of the intermediate 14 which was clarified to exhibit tautomeric equilibria between enol-hydrazine form A and keto-hydrazine form B by means of H-1 and C-13 NMR spectroscopy. Attempts to synthesize 3-alloxy-pyridazines 18 by reacting 11 with sodium alloxide afford N-allyl compounds 17.

  DOI：

  10.1002/prac.19973390104
• 作为产物：
  描述：

  4-(对氯苯基)-2-氧代丁酸 、 丙酮 在 氢氧化钾 作用下， 以 水 为溶剂， 以89%的产率得到2-Acetonyl-4-(p-chlorophenyl)-2-hydroxybutanoic Acid
  参考文献：
  名称：

  从4-芳基-2-氧代-丁酸†获得2,3-二氢哒嗪-3-酮和作为-triazino [3,4- a ]酞嗪环系统的†

  摘要：

  通过肼与4-（对氯苯基）-2-羟基-2-（2-氧代-2-取代的乙基）丁酸8的缩合反应合成了一系列新的2,3-二氢哒嗪-3-酮15。然后通过取代的苄基丙酮酸6与甲基烷基（芳基）酮的反应制备7。用冰醋酸和盐酸的混合物将8b-d脱水，得到4-（对-氯苯基）-2-（取代的苯甲酰基）。 -2-丁烯酸10. 10与肼的缩合反应以高收率得到15型化合物。另外，新系列的因为-三嗪[3,4- a ]酞嗪20是从取代的苄基丙酮酸6与肼苯哒嗪反应制得的，以酰肼19形式与PPA进行脱水环化反应得到20。结构分配基于1 H，13 C核磁共振和红外光谱。

  DOI：

  10.1002/jhet.5570240114

文献信息

• EL-ASHRY EL-SAYED H.; AMER ADEL; LABIB G. H.; RAHMAN MOHAMED M. ABDEL; EL+, J. HETEROCYCL. CHEM., 24,(1987) N 1, 63-68
  作者：EL-ASHRY EL-SAYED H.、 AMER ADEL、 LABIB G. H.、 RAHMAN MOHAMED M. ABDEL、 EL+

  DOI：——

  日期：——
• Access to the 2,3-dihydropyridazin-3-one and<i>as</i>-triazino[3,4-<i>a</i>]phthalazine ring systems from 4-aryl-2-oxo-butanoic acids
  作者：El-Sayed H. El-Ashry、Adel Amer、George H. Labib、Mohamed M. Abdel Rahman、Abdel Monem El-Massry

  DOI：10.1002/jhet.5570240114

  日期：1987.1

  ituted phenacyl)-2-butenoic acids 10. Condensation reaction of 10 with hydrazines gave type 15 compounds in good yields. Also, a new series of as-triazino[3,4-a]phthalazines 20 was obtained from the reaction of substituted benzylpyruvic acids 6 with hydralazine to give the hydralazones 19 which underwent dehydrative cyclization reaction with PPA to afford 20. Structure assignments are based on 1H,

  通过肼与4-（对氯苯基）-2-羟基-2-（2-氧代-2-取代的乙基）丁酸8的缩合反应合成了一系列新的2,3-二氢哒嗪-3-酮15。然后通过取代的苄基丙酮酸6与甲基烷基（芳基）酮的反应制备7。用冰醋酸和盐酸的混合物将8b-d脱水，得到4-（对-氯苯基）-2-（取代的苯甲酰基）。 -2-丁烯酸10. 10与肼的缩合反应以高收率得到15型化合物。另外，新系列的因为-三嗪[3,4- a ]酞嗪20是从取代的苄基丙酮酸6与肼苯哒嗪反应制得的，以酰肼19形式与PPA进行脱水环化反应得到20。结构分配基于1 H，13 C核磁共振和红外光谱。
• Dehydration of 2-(2-Arylethyl)-2-hydroxy-4-oxopentanoic Acids and their hydrazones to form heterocycles
  作者：Adel Amer、Abdel Moneim El Massry、Mohamed Badawi、Mohamed M. Abdel-Rahman、Safaa A. F. El Sayed、El Sayed H. El Ashry

  DOI：10.1002/prac.19973390104

  日期：——

  Dehydration of 2-(2-arylethyl)-2-hydroxy-4-oxopentanoic acids 1 with hydrochloric acid/acetic acid, affords 3-(2-arylethyl)-5-hydroxy-5-methyl-2(5H)-furanones 4. Compounds of type 1 and 4 represent suitable precursors for the formation of pyridazin-3-ones 7 as they smoothly react with hydrazine. A new series of s-triazolo[4,3-b]pyridazin-3-ones 12 and tetrazolo[1,5-b]pyridazines 15 are obtained from the 3-chloropyridazines 11 upon treatment with semicarbazide and sodium azide, respectively. Reaction of 11 with phenyl- acetyl-hydrazine provides 3-benzyl-6-phenyl-8-(2-phenyl-ethyl)-s-triazolo [4,3-b]pyridazine 13 via dehydrative cyclization of the intermediate 14 which was clarified to exhibit tautomeric equilibria between enol-hydrazine form A and keto-hydrazine form B by means of H-1 and C-13 NMR spectroscopy. Attempts to synthesize 3-alloxy-pyridazines 18 by reacting 11 with sodium alloxide afford N-allyl compounds 17.