methyl 1-(trimethylsilyl)-2-butyl-3-(4-nitrophenyl)cyclopropene-3-carboxylate | 1001206-34-3

• 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 1-(trimethylsilyl)-2-butyl-3-(4-nitrophenyl)cyclopropene-3-carboxylate
• 英文别名: methyl 2-butyl-1-(4-nitrophenyl)-3-trimethylsilylcycloprop-2-enecarboxylate；Methyl 2-butyl-1-(4-nitrophenyl)-3-trimethylsilylcycloprop-2-ene-1-carboxylate
• CAS: 1001206-34-3
• 化学式: C₁₈H₂₅NO₄Si
• 分子量: 347.486
• InChiKey: IYJPIXUDQROBDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(trimethylsilyl)-2-butyl-3-(4-nitrophenyl)cyclopropene-3-carboxylate 、 苯甲醛 在 三(2,4,6-三甲氧基苯基)磷 作用下， 以 1,4-二氧六环 为溶剂， 以86%的产率得到methyl 1-(trimethylsiloxyphenylmethyl)-2-butyl-3-(4-nitrophenyl)cyclopropene-3-carboxylate
  参考文献：
  名称：

  Sila Morita−Baylis−Hillman Reaction of Cyclopropenes

  摘要：

  The first example of sila-Morita-Bayis-Hillman reaction between 1-silylcyclopropenes and carbonyl compounds has been demonstrated. This novel phosphine-catalyzed transformation features a 1,3-Brook rearrangement/elimination cascade and provides convenient access to a variety of 1-(silyloxymethyl)cyclopropenes, which are not easily available via traditional methods.

  DOI：

  10.1021/ja077437s
• 作为产物：
  描述：

  三甲基氯硅烷 、 methyl 1-butyl-3-(4-nitrophenyl)cyclopropene-3-carboxylate 在 lithium hexamethyldisilazane 作用下， 以77%的产率得到methyl 1-(trimethylsilyl)-2-butyl-3-(4-nitrophenyl)cyclopropene-3-carboxylate
  参考文献：
  名称：

  Sila Morita−Baylis−Hillman Reaction of Cyclopropenes

  摘要：

  The first example of sila-Morita-Bayis-Hillman reaction between 1-silylcyclopropenes and carbonyl compounds has been demonstrated. This novel phosphine-catalyzed transformation features a 1,3-Brook rearrangement/elimination cascade and provides convenient access to a variety of 1-(silyloxymethyl)cyclopropenes, which are not easily available via traditional methods.

  DOI：

  10.1021/ja077437s

文献信息

• Copper-catalyzed silylation of cyclopropenes using (trifluoromethyl)trimethylsilane
  作者：Euan A. F. Fordyce、Yi Wang、Thomas Luebbers、Hon Wai Lam

  DOI：10.1039/b717568j

  日期：——

  A variety of cyclopropenes undergo direct silylation using (trifluoromethyl)trimethylsilane in the presence of a copper–bisphosphine catalyst; under these conditions, cyclopropenes that might otherwise undergo ring-opening are silylated efficiently.

  在铜-双膦催化剂的作用下，多种环丙烯在（三氟甲基）三甲基硅烷的作用下直接进行硅烷化反应；在这些条件下，原本可能发生开环反应的环丙烯被有效地进行了硅烷化。
• Sila Morita−Baylis−Hillman Reaction of Cyclopropenes
  作者：Stepan Chuprakov、Denis A. Malyshev、Alexander Trofimov、Vladimir Gevorgyan

  DOI：10.1021/ja077437s

  日期：2007.12.1

  The first example of sila-Morita-Bayis-Hillman reaction between 1-silylcyclopropenes and carbonyl compounds has been demonstrated. This novel phosphine-catalyzed transformation features a 1,3-Brook rearrangement/elimination cascade and provides convenient access to a variety of 1-(silyloxymethyl)cyclopropenes, which are not easily available via traditional methods.