trans-1,2-divinylcyclopropane | 2984-58-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: trans-1,2-divinylcyclopropane
• 英文别名: trans-1,2-Divinyl-cyclopropan；(1S,2S)-1,2-bis(ethenyl)cyclopropane
• CAS: 2984-58-9；17085-85-7；22770-04-3；38206-80-3；61688-04-8；87858-60-4；87858-61-5
• 化学式: C₇H₁₀
• 分子量: 94.1564
• InChiKey: UEYYOGFVPAORCH-RNFRBKRXSA-N

物化性质

• 沸点：
  40 °C(Press: 2 Torr)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trans-1,2-divinylcyclopropane 生成 1,4-环庚二烯
  参考文献：
  名称：

  Hydrogen-deuterium fractionation factors for hydrogen-sp2 carbon bonds in olefins and allyl radicals

  摘要：

  Thermally induced 3,3-shift of trans- 1,2-divinylcyclopropane, 1, and trans-1,2-bis(2',2'-dideuteriovinyl)cyclopropane, 1-d4, to cycloheptadiene has a kinetic isotope effect of 1.08 +/- 0.02/D when extrapolated to 25-degrees-C. To the extent that the transition state resembles two allyl radicals, the kinetic effect is the fractionation factor for deuterium between sp2 allyl radical carbon and sp2 olefinic carbon. AM1 calculations on allyl radicals reveal a similar fractionation factor. The new value for the FF of allyl radical requires a correction to previously developed linear free energy relationships for kinetic and equilibrium isotope effect in 3,3-shifts and Diels-Alder reactions. The corrections are moderate, altering the previously determined extent of bond breaking and bond making by up to 50% only when there is little bond making, but do not alter the relative extents of bond making and breaking in the large number of compounds examined.

  DOI：

  10.1021/ja00064a017
• 作为产物：
  描述：

  环丙甲醇,2-乙烯基-,反- 在 CrO₃-3.5-dimethylpyrazole 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 trans-1,2-divinylcyclopropane
  参考文献：
  名称：

  Hydrogen-deuterium fractionation factors for hydrogen-sp2 carbon bonds in olefins and allyl radicals

  摘要：

  Thermally induced 3,3-shift of trans- 1,2-divinylcyclopropane, 1, and trans-1,2-bis(2',2'-dideuteriovinyl)cyclopropane, 1-d4, to cycloheptadiene has a kinetic isotope effect of 1.08 +/- 0.02/D when extrapolated to 25-degrees-C. To the extent that the transition state resembles two allyl radicals, the kinetic effect is the fractionation factor for deuterium between sp2 allyl radical carbon and sp2 olefinic carbon. AM1 calculations on allyl radicals reveal a similar fractionation factor. The new value for the FF of allyl radical requires a correction to previously developed linear free energy relationships for kinetic and equilibrium isotope effect in 3,3-shifts and Diels-Alder reactions. The corrections are moderate, altering the previously determined extent of bond breaking and bond making by up to 50% only when there is little bond making, but do not alter the relative extents of bond making and breaking in the large number of compounds examined.

  DOI：

  10.1021/ja00064a017

文献信息

• Hydrogen-deuterium fractionation factors for hydrogen-sp2 carbon bonds in olefins and allyl radicals
  作者：Joseph J. Gajewski、Leif P. Olson、Kenneth J. Tupper

  DOI：10.1021/ja00064a017

  日期：1993.6

  Thermally induced 3,3-shift of trans- 1,2-divinylcyclopropane, 1, and trans-1,2-bis(2',2'-dideuteriovinyl)cyclopropane, 1-d4, to cycloheptadiene has a kinetic isotope effect of 1.08 +/- 0.02/D when extrapolated to 25-degrees-C. To the extent that the transition state resembles two allyl radicals, the kinetic effect is the fractionation factor for deuterium between sp2 allyl radical carbon and sp2 olefinic carbon. AM1 calculations on allyl radicals reveal a similar fractionation factor. The new value for the FF of allyl radical requires a correction to previously developed linear free energy relationships for kinetic and equilibrium isotope effect in 3,3-shifts and Diels-Alder reactions. The corrections are moderate, altering the previously determined extent of bond breaking and bond making by up to 50% only when there is little bond making, but do not alter the relative extents of bond making and breaking in the large number of compounds examined.

表征谱图