1-phenyl-propynone-diethylacetal | 87406-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-propynone-diethylacetal
• 英文别名: 1-Phenyl-propinon-diaethylacetal；(1,1-diethoxy-2-propynyl)-benzene；1,1-Diethoxyprop-2-ynylbenzene
• CAS: 87406-33-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: XJRNQVQQCBYCTM-UHFFFAOYSA-N

物化性质

• 沸点：
  80-81 °C(Press: 2 Torr)
• 密度：
  1.0085 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-propynone-diethylacetal 、 2,4-二硝基苯肼 生成 Phenyl-ethinyl-keton-2.4-dinitro-phenylhydrazon
  参考文献：
  名称：

  Normant,H.; Lecolier,S., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1960, vol. 250, p. 722 - 724

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha- 溴苯乙烯 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 生成 1-phenyl-propynone-diethylacetal
  参考文献：
  名称：

  Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.

  摘要：

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.

  DOI：

  10.3891/acta.chem.scand.50-0446

文献信息

• A Route from 1,1,1,3-Tetrachloro-3-phenylpropane to Ethynyl Phenyl Ketone Involving Elimination of Hydrogen Chloride and 1,3-Proton Transfer
  作者：Takeo Akiyama、Yasuki Yoshida、Tokiko Hanawa、Akira Sugimori

  DOI：10.1246/bcsj.56.1795

  日期：1983.6

  The treatment of 1,1,1,3-tetrachloro-3-phenylpropane with alkali in ethanol affords ethynyl phenyl ketone and its acetal in good yields. This reaction proceeds through the elimination of hydrogen chloride and an efficient 1,3-proton transfer catalyzed by base. Ethyl cinnamate is obtained in only 2% yield.

  在乙醇中用碱处理 1,1,1,3-四氯-3-苯基丙烷，以良好的收率得到乙炔基苯基酮及其缩醛。该反应通过消除氯化氢和由碱催化的有效 1,3-质子转移进行。肉桂酸乙酯的产率仅为 2%。
• Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.
  作者：Einar Bakstad、Leiv K. Sydnes、Anders Kjær、Salka E. Nielsen、Carl E. Olsen、Kirsi Ranta、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1029

  日期：——

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.
• Sacharkin; Kornewa, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 1344,1347, 1348; engl. Ausg. S. 1363, 1366
  作者：Sacharkin、Kornewa

  DOI：——

  日期：——
• AKIYAMA, TAKEO;YOSHIDA, YASUKI;HANAWA, TOKIKO;SUGIMORI, AKIRA, BULL. CHEM. SOC. JAP., 1983, 56, N 6, 1795-1798
  作者：AKIYAMA, TAKEO、YOSHIDA, YASUKI、HANAWA, TOKIKO、SUGIMORI, AKIRA

  DOI：——

  日期：——
• Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.
  作者：Leiv K. Sydnes、Einar Bakstad、Morten Heide、Georg W. Jensen、Inge L. Møller、Ruby I. Nielsen、Carl Erik Olsen、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0446

  日期：——

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.