Methyl 2-<4-<2-(2-Propenyl)phenyl>buta-1,3-diynyl>benzoate | 147298-34-8

• 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: Methyl 2-<4-<2-(2-Propenyl)phenyl>buta-1,3-diynyl>benzoate
• 英文别名: methyl 2-<4-(2-(2-propen-1-yl)phenyl)buta-1,3-diynyl>benzoate；methyl 2-[4-(2-prop-2-enylphenyl)buta-1,3-diynyl]benzoate
• CAS: 147298-34-8
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: DNEHDBWIPXMLFS-UHFFFAOYSA-N

物化性质

• 沸点：
  458.9±45.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Methyl 2-<4-<2-(2-Propenyl)phenyl>buta-1,3-diynyl>benzoate 在 Rh2[(+/-)-mandelate]4 potassium trimethylsilonate 、 氯甲酸甲酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 5,11-Bis<(2-allylphenyl)ethynyl>indeno<1,2-b>fluorene-6,12-dione
  参考文献：
  名称：

  A comparative study of the decomposition of o-alkynyl-substituted aryl diazo ketones. Synthesis of polysubstituted .beta.-naphthols via arylketene intermediates

  摘要：

  The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl alpha-diazoaceto- and propiophenone derivatives have been studied. The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion. Thermolysis or photolysis of o-alkynyl alpha-diazopropiophenone derivatives yields polysubstituted beta-naphthols. These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynyl substituent. In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered pi-system producing a vinyl carbenoid intermediate. Further reaction of the cyclized carbenoid with the starting diazo compound furnishes a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis. Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.

  DOI：

  10.1021/jo00075a045
• 作为产物：
  描述：

  邻碘溴苯 在 copper(l) iodide 、 四溴化碳 、 trans-bis(triphenylphosphine)palladium(II) chloride 、 盐酸羟胺 、 四丁基氟化铵 、 叔丁基锂 、 正丁胺 、 三乙胺 、 三苯基膦 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.66h， 生成 Methyl 2-<4-<2-(2-Propenyl)phenyl>buta-1,3-diynyl>benzoate
  参考文献：
  名称：

  Padwa, Albert; Austin, David J.; Gareau, Yves, Journal of the American Chemical Society, 1993, vol. 115, # 7, p. 2637 - 2647

  摘要：

  DOI：

文献信息

• Padwa Albert, Chiacchio Ugo, Fairfax David J., Kassir Jamal M., Litrico A+, J. Org. Chem, 58 (1993) N 23, S 6429-6437
  作者：Padwa Albert, Chiacchio Ugo, Fairfax David J., Kassir Jamal M., Litrico A+

  DOI：——

  日期：——