3-甲氧基-4-(2-苯基乙炔基)环丁-3-烯-1,2-二酮 | 113976-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲氧基-4-(2-苯基乙炔基)环丁-3-烯-1,2-二酮
• 英文名称: 3-(phenylethynyl)-4-methoxy-3-cyclobutene-1,2-dione
• 英文别名: 3-methoxy-4-(phenylethynyl)-3-cyclobutene-1,2-dione；3-methoxy-2-(phenylacetynyl)cyclobutenedione；3-Methoxy-4-(phenylethynyl)cyclobut-3-ene-1,2-dione；3-methoxy-4-(2-phenylethynyl)cyclobut-3-ene-1,2-dione
• CAS: 113976-82-2
• 化学式: C₁₃H₈O₃
• 分子量: 212.205
• InChiKey: VYGRGZSBTQUXQE-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  345.2±52.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲氧基-4-(2-苯基乙炔基)环丁-3-烯-1,2-二酮 在 叔丁基锂 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-methoxy-2-(phenylethynyl)-5-(phenylmethyl)-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  Perri, Steven T.; Moore, Harold W., Journal of the American Chemical Society, 1990, vol. 112, # 5, p. 1897 - 1905

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-Dimethoxy-4-hydroxy-4-(phenylethynyl)-2-cyclobuten-1-one 在 硫酸 、 三氟乙酸酐 作用下， 生成 3-甲氧基-4-(2-苯基乙炔基)环丁-3-烯-1,2-二酮
  参考文献：
  名称：

  Synthesis of 4-substituted-3-alkoxy-3-cyclobutene-1,2-diones

  摘要：

  DOI：

  10.1021/jo00246a016

文献信息

• Synthesis of indolizine-5,8-diones and [3.2.2]cyclazines
  作者：Benjamin R. Yerxa、Harold W. Moore

  DOI：10.1016/s0040-4039(00)74750-2

  日期：1992.12

  subsequent oxidation to the rare indolizine-5,8-diones is described. When the rearrangement is carried out in the presence of DMAD the indolizines are trapped in an 8+2 cycloaddition to give [3.2.2]cyclazines.

  描述了热诱导的4-（1-吡咯基）-4-三甲基甲硅烷氧基环丁烯酮的环膨胀成5-羟基-8-三甲基甲硅烷氧基吲哚并随后氧化成稀有的吲哚嗪-5，8-二酮。当在DMAD存在下进行重排时，吲哚嗪被困在8 + 2环加成反应中，生成[3.2.2]环嗪。
• Rearrangement of 4-alkynylcyclobutenones. A new synthesis of 1,4-benzoquinones
  作者：Lafayette D. Foland、J. Olle Karlsson、Steven T. Perri、Rudolf Schwabe、Simon L. Xu、Sanjay Patil、Harold W. Moore

  DOI：10.1021/ja00185a030

  日期：1989.2
• <i>o</i>-Quinone Methides from 4-Allenylcyclobutenones:  Synthesis and Chemistry
  作者：Meng Taing、Harold W. Moore

  DOI：10.1021/jo951445m

  日期：1996.1.1

  Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30 degrees C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.
• Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Enantiomerically Pure Pyranoquinones from 4-(4-Oxo-1,6-enynyl)-4-hydroxycyclobutenones and 4-(4-Oxo-1,6-dialkynyl)-4-hydroxycyclobutenones
  作者：Yifeng Xiong、Haiji Xia、Harold W. Moore

  DOI：10.1021/jo00125a037

  日期：1995.10

  Thermolysis of 4-(4-oxo-1,6-enynyl)-4-hydroxycyclobutenones 23 in refluxing toluene provides an enantiospecific synthesis of pyranoquinones 27. The 4-methoxy analog 32 was shown to give a quinone methide 35 and ultimately the trimer 36.
• Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00027a057

  日期：1992.1

  A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported. A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples. The chlorination is envisaged to involve the corresponding homoaromatic carbocation, and the site of chlorination takes place preferentially at the position substituted with the greater cation-stabilizing substituent. Specifically, this follows the general order of allyl > benzyl > alkyl > propargyl. The 4-chlorocyclobutenones prepared in this study were shown to be useful synthetic precursors to highly substituted chlorophenols and chloronaphthols.