(3-Methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-trimethylsilane | 877875-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3-Methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-trimethylsilane
• 英文别名: (3-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-trimethylsilane
• CAS: 877875-66-6
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: CRQQGELPAYUTIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-Methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-trimethylsilane 、 马来酸酐 以 邻二氯苯 为溶剂， 反应 2.0h， 生成 (3aR,4S,9aR)-7-Methoxy-4-trimethylsilanylmethyl-3a,4,9,9a-tetrahydro-naphtho[2,3-c]furan-1,3-dione 、 (3aS,4S,9aS)-7-Methoxy-4-trimethylsilanylmethyl-3a,4,9,9a-tetrahydro-naphtho[2,3-c]furan-1,3-dione
  参考文献：
  名称：

  Accelerated Electrocyclic Ring-Opening of Benzocyclobutenes under the Influence of a β-Silicon Atom

  摘要：

  A significant acceleration effect of a beta-silicon atom was observed on the electrocyclic ring-opening reaction of benzocyclobutene derivatives to form o-quinodimethanes. This acceleration effect could be attributed to an electronic sigma-donating nature of the C(alpha)-Si(beta) bond, associated with alpha-anion driven pericyclic reactions.

  DOI：

  10.1021/ja055505+
• 作为产物：
  描述：

  4-methoxy-1-[(trimethylsilyl)methyl]benzocyclobutene-1-carbonitrile 在 氨 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.25h， 以76%的产率得到(3-Methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-trimethylsilane
  参考文献：
  名称：

  Accelerated Electrocyclic Ring-Opening of Benzocyclobutenes under the Influence of a β-Silicon Atom

  摘要：

  A significant acceleration effect of a beta-silicon atom was observed on the electrocyclic ring-opening reaction of benzocyclobutene derivatives to form o-quinodimethanes. This acceleration effect could be attributed to an electronic sigma-donating nature of the C(alpha)-Si(beta) bond, associated with alpha-anion driven pericyclic reactions.

  DOI：

  10.1021/ja055505+

文献信息

• Accelerated Electrocyclic Ring-Opening of Benzocyclobutenes under the Influence of a β-Silicon Atom
  作者：Yuji Matsuya、Noriko Ohsawa、Hideo Nemoto

  DOI：10.1021/ja055505+

  日期：2006.1.1

  A significant acceleration effect of a beta-silicon atom was observed on the electrocyclic ring-opening reaction of benzocyclobutene derivatives to form o-quinodimethanes. This acceleration effect could be attributed to an electronic sigma-donating nature of the C(alpha)-Si(beta) bond, associated with alpha-anion driven pericyclic reactions.