β-cyclopropyl-(3H)-indene | 153756-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: β-cyclopropyl-(3H)-indene
• 英文别名: 2-cyclopropylindene；2-Cyclopropyl-1H-indene
• CAS: 153756-10-6
• 化学式: C₁₂H₁₂
• 分子量: 156.227
• InChiKey: KMXOYTAWHAROBD-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：

  β-cyclopropyl-(3H)-indene 以 环己烷 为溶剂， 生成 α-cyclopropyl-(3H)-indene 、 1-cyclopropylindene 、 2,3,3a,8-tetrahydrocyclopentaindene
  参考文献：
  名称：

  上激发态光化学：2-和3-环丙基茚的溶液和气相光化学和光物理1

  摘要：

  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）。

  DOI：

  10.1021/ja981397y
• 作为产物：
  描述：

  2-茚酮 在 硫酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 β-cyclopropyl-(3H)-indene
  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

文献信息

• Nickel-catalyzed Carboannulation Reaction of <i>o</i>-Bromobenzyl Zinc Bromide with Unsaturated Compounds
  作者：Ruixue Deng、Liangdong Sun、Zhi Li

  DOI：10.1021/ol702167t

  日期：2007.12.1

  A number of indenes have been prepared in good yields by treating o-bromobenzyl zinc bromide 1 with various terminal and internal alkynes in the presence of a nickel catalyst. The nickel-catalyzed carboannulation reaction was successfully extended to the synthesis of indane derivatives by reaction of 1 with acrylates and styrene.

  在镍催化剂的存在下，通过用各种末端和内部炔烃处理邻溴苄基溴化锌1，已经以高收率制备了许多茚。通过1与丙烯酸酯和苯乙烯的反应，镍催化的碳环化反应成功地扩展到了茚满衍生物的合成。
• Cyclopropyl Substituted Metallocene Catalysts
  申请人：ExxonMobil Chemical Patents Inc.

  公开号：US20150025207A1

  公开（公告）日：2015-01-22

  This invention relates to a novel group 2, 3 or 4 transition metal metallocene catalyst compound having at least one arenyl ligand substituted with: 1) a cyclopropyl group and, optionally, 2) at least one other group, such as a hydrocarbyl, a heteroatom or a heteroatom containing group.

  本发明涉及一种新型的2、3或4族过渡金属茂金属催化剂化合物，其至少具有一个芳基配体，该配体被取代为：1）环丙基基团，可选地，2）至少一个其他基团，例如烃基，杂原子或含杂原子的基团。
• 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）。
• 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.