1,1,1-trichloro-4-hydroxy-4-(1-naphthyl)-3-buten-2-one | 1372713-47-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,1,1-trichloro-4-hydroxy-4-(1-naphthyl)-3-buten-2-one
• 英文别名: (Z)-1,1,1-trichloro-4-hydroxy-4-naphthalen-1-ylbut-3-en-2-one
• CAS: 1372713-47-7
• 化学式: C₁₄H₉Cl₃O₂
• 分子量: 315.583
• InChiKey: BTPYDUGVNBACIQ-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-Acetonaphthone dimethyl acetal 在 吡啶 、 硫酸 、 水 作用下， 以 氯仿 为溶剂， 反应 10.0h， 生成 1,1,1-trichloro-4-hydroxy-4-(1-naphthyl)-3-buten-2-one
  参考文献：
  名称：

  Synthesis and Structure of Novel 1-Aryl-4,4,4-trichloro-1,3-butanediones

  摘要：

  Novel 1-aryl-4,4,4-trichloro-1,3-butanediones in good yields (80-97%) were synthesized in one pot through acetal acylation with trichloroacetyl chloride followed by acid hydrolysis. Structures of all compounds were elucidated by elemental analysis, mass spectrometry, and H-1/C-13 nuclear magnetic resonance (NMR) measurements. The H-1/C-13 NMR data showed that trichloromethyl-beta-diketones 2a-k in solution are predominantly ketoenol. However, the spectroscopic data from 4,4,4-trichloro-2-methyl-1-phenyl-1,3-butabedione (2l) with methyl substituent between carbonyls showed a bias toward the diketo form in solution. X-ray diffraction of monocrystals from 2g and 2i showed that these compounds are cis-ketoenol tautomers.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communcations (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2010.530376

文献信息

• Synthesis and Structure of Novel 1-Aryl-4,4,4-trichloro-1,3-butanediones
  作者：Alex F. C. Flores、Mauro J. Martins、Leandro M. Frigo、Pablo Machado、Patrick T. Campos、Juliana L. Malavolta

  DOI：10.1080/00397911.2010.530376

  日期：2012.3.1

  Novel 1-aryl-4,4,4-trichloro-1,3-butanediones in good yields (80-97%) were synthesized in one pot through acetal acylation with trichloroacetyl chloride followed by acid hydrolysis. Structures of all compounds were elucidated by elemental analysis, mass spectrometry, and H-1/C-13 nuclear magnetic resonance (NMR) measurements. The H-1/C-13 NMR data showed that trichloromethyl-beta-diketones 2a-k in solution are predominantly ketoenol. However, the spectroscopic data from 4,4,4-trichloro-2-methyl-1-phenyl-1,3-butabedione (2l) with methyl substituent between carbonyls showed a bias toward the diketo form in solution. X-ray diffraction of monocrystals from 2g and 2i showed that these compounds are cis-ketoenol tautomers.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communcations (R) to view the free supplemental file.