triisopropylsilyl-1a,7b-Dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: triisopropylsilyl-1a,7b-Dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate
• 英文别名: tri(propan-2-yl)silyl (1R,1aS,7bR)-1a,7b-dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate
• 化学式: C₂₁H₃₀O₂Si
• 分子量: 342.554
• InChiKey: NXKXSTIMTDKMEM-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氮杂萘 、 (furan-2-yloxy)triisopropylsilane 在 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 60.0h， 以99%的产率得到triisopropylsilyl-1a,7b-Dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate
  参考文献：
  名称：

  Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid

  摘要：

  A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.

  DOI：

  10.1021/ja308858y

文献信息

• Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid
  作者：Simon N. Kessler、Markus Neuburger、Hermann A. Wegner

  DOI：10.1021/ja308858y

  日期：2012.10.31

  A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.