trans-1-formyl-2-(1-methylethenyl)cyclopropane | 93782-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: trans-1-formyl-2-(1-methylethenyl)cyclopropane
• 英文别名: (1R,2R)-2-prop-1-en-2-ylcyclopropane-1-carbaldehyde
• CAS: 93782-33-3；137694-55-4
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: NUBIUCDKEFZXAY-BQBZGAKWSA-N

物化性质

• 沸点：
  139.4±29.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  碘化异丙基三苯鏻 、 trans-1-formyl-2-(1-methylethenyl)cyclopropane 在 正丁基锂 作用下， 生成 (-)-rothrockene
  参考文献：
  名称：

  [2 + 1] Cycloaddition of 1-Seleno-2-silylethenes. Selenium-Assisted 1,2-Silicon Shift for Cyclopropanation

  摘要：

  A novel one-step [2 + 1] cycloaddition synthesis of cyclopropanes has been developed. Reaction of (E)-1-(phenylseleno)-2-silylethenes 1a,b with vinyl ketones 2a-d and acrolein (2e) in the presence of SnCl4 gave cyclopropane products by a formal [2 + 1] cycloaddition accompanied by 1,2-silicon migration rather than by [2 + 2] cycloaddition. This facile 1,2-silicon shift is rationalized by a remarkable selenium effect. A generated beta-silicon-stabilized zwitterion A is transformed by a 1,2-silicon shift to the more stable selenium-bridged intermediate C. Ab initio MO calculations for model compounds clearly demonstrate that the intermediate C is more stable than A. The selenium-bridged geometry of C shows that preference is for formation of a cyclopropane ring instead of a cyclobutane ring.

  DOI：

  10.1021/ja00085a015
• 作为产物：
  描述：

  trans-1-(1-methylethenyl)-2-(1-(phenylseleno)-1-(trimethylsilyl)methyl)cyclopropane 以39%的产率得到
  参考文献：
  名称：

  Yamazaki Shoko, Tanaka Mayumi, Yamaguchi Akio, Yamabe Shinichi, J. Amer. Chem. Soc, 116 (1994) N 6, S 2356-2365

  摘要：

  DOI：

文献信息

• [2 + 1] Cycloaddition of (E)-1-(phenylseleno)-2-(trimethylsilyl)ethene. Novel cyclopropane ring formation by a 1,2-shift of a trimethylsilyl group
  作者：Shoko Yamazaki、Shigeki Katoh、Shinichi Yamabe

  DOI：10.1021/jo00027a003

  日期：1992.1

  Reaction of (E)-1-(phenylseleno)-2-(trimethylsilyl)ethene (1) with vinyl ketones 2a-d in the presence of SnCl4 gave cyclopropane products by a formal [2 + 1] cycloaddition accompanied by 1,2-silicon migration rather than [2 + 2] cycloaddition.
• Yamazaki Shoko, Tanaka Mayumi, Yamaguchi Akio, Yamabe Shinichi, J. Amer. Chem. Soc, 116 (1994) N 6, S 2356-2365
  作者：Yamazaki Shoko, Tanaka Mayumi, Yamaguchi Akio, Yamabe Shinichi

  DOI：——

  日期：——
• [2 + 1] Cycloaddition of 1-Seleno-2-silylethenes. Selenium-Assisted 1,2-Silicon Shift for Cyclopropanation
  作者：Shoko Yamazaki、Mayumi Tanaka、Akio Yamaguchi、Shinichi Yamabe

  DOI：10.1021/ja00085a015

  日期：1994.3

  A novel one-step [2 + 1] cycloaddition synthesis of cyclopropanes has been developed. Reaction of (E)-1-(phenylseleno)-2-silylethenes 1a,b with vinyl ketones 2a-d and acrolein (2e) in the presence of SnCl4 gave cyclopropane products by a formal [2 + 1] cycloaddition accompanied by 1,2-silicon migration rather than by [2 + 2] cycloaddition. This facile 1,2-silicon shift is rationalized by a remarkable selenium effect. A generated beta-silicon-stabilized zwitterion A is transformed by a 1,2-silicon shift to the more stable selenium-bridged intermediate C. Ab initio MO calculations for model compounds clearly demonstrate that the intermediate C is more stable than A. The selenium-bridged geometry of C shows that preference is for formation of a cyclopropane ring instead of a cyclobutane ring.