Methyl 2-<2-(trimethylsilyl)ethyn-1-yl>acrylate | 159111-72-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 2-<2-(trimethylsilyl)ethyn-1-yl>acrylate
• 英文别名: methyl α-[(trimethylsilyl)ethynyl]acrylate；Methyl 2-methylidene-4-trimethylsilylbut-3-ynoate
• CAS: 159111-72-5
• 化学式: C₉H₁₄O₂Si
• 分子量: 182.294
• InChiKey: DJCGQIUORJFWDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 2-<2-(trimethylsilyl)ethyn-1-yl>acrylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  拟青霉素A的全合成。

  摘要：

  DOI：

  10.1002/anie.200605058
• 作为产物：
  描述：

  2-溴丙-2-烯酸甲酯 、 三甲基乙炔基硅 在 钯 作用下， 以76%的产率得到Methyl 2-<2-(trimethylsilyl)ethyn-1-yl>acrylate
  参考文献：
  名称：

  An expedient and stereoselective route to the perhydrophenanthrene skeleton via sequential Diels-Alder reactions

  摘要：

  A novel and efficient stereoselective synthesis of the perhydrophenanthrene skeleton was achieved using a sequential Diels-Alder cycloaddition strategy involving enyne 10 and bis-diene 8.

  DOI：

  10.1016/s0040-4039(00)77246-7

文献信息

• An expedient and stereoselective route to the perhydrophenanthrene skeleton via sequential Diels-Alder reactions
  作者：Claude Spino、Jason Crawford

  DOI：10.1016/s0040-4039(00)77246-7

  日期：1994.8

  A novel and efficient stereoselective synthesis of the perhydrophenanthrene skeleton was achieved using a sequential Diels-Alder cycloaddition strategy involving enyne 10 and bis-diene 8.
• Creating Quaternary Centers with High Exo Stereoselectivity Using Activated α-Alkynyl Dienophiles
  作者：Sun-Joon Min、Gavin O. Jones、K. N. Houk、Samuel J. Danishefsky

  DOI：10.1021/ja073528d

  日期：2007.8.1

  Ethynyl substituents were used to direct a highly exoselective creation of quaternary carbon centers in Diels-Alder cycloaddition reactions involving activated alpha-alkynyl dienophiles. The origins of electronic activation and the high stereoselectivities of these reactions were investigated by the B3LYP density functional method.
• Sequential Diels-Alder Reactions on a 1,3,7,9-Tetraene: An Efficient and Stereoselective Route to the Perhydrophenanthrene Skeleton
  作者：Claude Spino、Jason Crawford、John Bishop

  DOI：10.1021/jo00109a014

  日期：1995.2

  A novel, efficient, and stereoselective route to the perhydrophenanthrene skeleton is described utilizing sequential Diels-Alder reactions of methyl (trimethylsilyl)ethynyl}aclylate with a 1,3,7,9-tetraene (bis-diene).
• Total Synthesis of Paecilomycine A
  作者：Sun-Joon Min、Samuel J. Danishefsky

  DOI：10.1002/anie.200605058

  日期：2007.3.19