α-cyclopropyl-(3H)-indene | 153756-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: α-cyclopropyl-(3H)-indene
• 英文别名: 3-Cyclopropyl-1H-indene；3-cyclopropylindene
• CAS: 153756-09-3
• 化学式: C₁₂H₁₂
• 分子量: 156.227
• InChiKey: BQZHPPQEBJXLMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  α-cyclopropyl-(3H)-indene 在 9-噻吨酮 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Are Perpendicular Alkene Triplets Just 1,2-Biradicals? Studies with the Cyclopropylcarbinyl Clock

  摘要：

  Thermochemical studies of perpendicular alkene triplets demonstrate that their energies are almost exactly those expected from Benson estimations using group equivalents for appropriate free radicals as models for the termini (the two essential carbons of the alkene triplet). If these species are to be described as 1,2-biradicals, their reactivities in reactions for which the termini act independently should be similar to corresponding reactivities for appropriate free-radical models. We have used the ''cyclopropylcarbinyl clock'', the rearrangement of a cyclopropylcarbinyl radical to the corresponding homoallyl radical, to test such a model. We have synthesized cis- and trans-beta-cyclopropylstyrene (cis-1 and trans-1), alpha-cyclopropylstyrene (2), alpha-cyclopropylindene (3), and beta-cyclopropylindene (4). We have studied their triplet chemistry and have examined the transients produced upon triplet sensitization by nanosecond laser flash photolysis. The results are consistent with two basic hypotheses: (1) that, when able to access the perpendicular configuration, cyclopropylcarbinyl ring opening occurs at the rate expected from an appropriate monoradical model and (2) that, when constrained in a higher energy (near-planar) geometry, the rate of ring opening is accelerated.

  DOI：

  10.1021/ja00085a005
• 作为产物：
  描述：

  1-茚酮 在 aluminum oxide 、 三(3,6-二氧杂庚基)胺 、 双(三甲基硅烷基)氨基钾 作用下， 以 正戊烷 为溶剂， 反应 27.0h， 生成 α-cyclopropyl-(3H)-indene
  参考文献：
  名称：

  9-环亚丙基-9 H-芴的正式[4 + 2]二聚

  摘要：

  具有固定在共面构象中的芳基取代基的亚甲基环丙烷7和8分别显示形成10和11时非常易于二聚。

  DOI：

  10.1002/jlac.199619961110

文献信息

• Upper Excited State Photochemistry:  Solution and Gas Phase Photochemistry and Photophysics of 2- and 3-Cyclopropylindene¹
  作者：Tim Waugh、Harry Morrison

  DOI：10.1021/ja981397y

  日期：1999.4.1

  The cyclopropylcarbinyl radical rearrangement has been used to probe the photochemistry and photophysics of S2 and S1 in 2-cyclopropylindene (2CPI) and 3-cyclopropylindene (3CPI). Studies in solution and the gas phase are described. Population of S2 with 254 nm light excitation in the gas phase produces the anticipated ring expansion products 2,3,3a,8-tetrahydrocyclopenta[a]indene (1, Φ1 = 0.1) and

  环丙基羰基重排已被用于探测 S2 和 S1 在 2-环丙基茚 (2CPI) 和 3-环丙基茚 (3CPI) 中的光化学和光物理。描述了溶液和气相的研究。S2 在气相中用 254 nm 光激发生成预期的扩环产物 2,3,3a,8-四氢环戊二烯 [a] 茚 (1, Φ1 = 0.1) 和 1,3,3a,8-四氢环戊二烯 [a] ]茚 (2, Φ2 = 0.06) 分别来自 2CPI 和 3CPI（方案 3）。直接激发到溶液中 2CPI 的 S2 状态 (254 nm) 也会产生化合物 1。溶液相化学的效率是激发波长的函数（Φ1 = 0.022 和 0.006，分别为 254 和 280 nm）。2CPI 的溶液相激发光谱显示出对监测波长的异常依赖性，这归因于构象平衡。相对于 t...，环丙基茚的 S1 单线态寿命非常短（2CPI 和 3CPI 分别为 0.39 和 1.0 ns）。
• A Formal [4 + 2] Dimerization of 9-Cyclopropylidene-9H-fluorene
  作者：Gerald Dyker、Gerhard Hillebrand、Ludger Ernst、Ina Dix、Peter G. Jones

  DOI：10.1002/jlac.199619961110

  日期：1996.11

  The methylenecyclopropanes 7 and 8, with aryl substituents fixed in a coplanar conformation, show an extraordinary readiness to dimerize with formation of 10 and 11, respectively.

  具有固定在共面构象中的芳基取代基的亚甲基环丙烷7和8分别显示形成10和11时非常易于二聚。
• Are Perpendicular Alkene Triplets Just 1,2-Biradicals? Studies with the Cyclopropylcarbinyl Clock
  作者：Richard A. Caldwell、Lingwen Zhou

  DOI：10.1021/ja00085a005

  日期：1994.3

  Thermochemical studies of perpendicular alkene triplets demonstrate that their energies are almost exactly those expected from Benson estimations using group equivalents for appropriate free radicals as models for the termini (the two essential carbons of the alkene triplet). If these species are to be described as 1,2-biradicals, their reactivities in reactions for which the termini act independently should be similar to corresponding reactivities for appropriate free-radical models. We have used the ''cyclopropylcarbinyl clock'', the rearrangement of a cyclopropylcarbinyl radical to the corresponding homoallyl radical, to test such a model. We have synthesized cis- and trans-beta-cyclopropylstyrene (cis-1 and trans-1), alpha-cyclopropylstyrene (2), alpha-cyclopropylindene (3), and beta-cyclopropylindene (4). We have studied their triplet chemistry and have examined the transients produced upon triplet sensitization by nanosecond laser flash photolysis. The results are consistent with two basic hypotheses: (1) that, when able to access the perpendicular configuration, cyclopropylcarbinyl ring opening occurs at the rate expected from an appropriate monoradical model and (2) that, when constrained in a higher energy (near-planar) geometry, the rate of ring opening is accelerated.