[4.4]paracyclophane | 502-08-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [4.4]paracyclophane
• 英文别名: <4.4>paracyclophane；[4.4]Paracyclophan；Tricyclo<12.2.2.2^6.9>eicosa-6,8,14,16,17,19-hexaen-<4.4>paracyclophan；<4,4>-Paracyclophan；<4.4>-Paracyclophan；<4.4>Paracyclophan；[4,4]Paracyclophane；tricyclo[12.2.2.26,9]icosa-1(17),6,8,14(18),15,19-hexaene
• CAS: 502-08-9
• 化学式: C₂₀H₂₄
• 分子量: 264.411
• InChiKey: NETBDWKOMKTAOP-UHFFFAOYSA-N

物化性质

• 熔点：
  146.2-147.3 °C(Solv: ethanol (64-17-5))
• 沸点：
  419.8±40.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  [4.4]paracyclophane 在 三氟化硼 、 硝酸 、 溶剂黄146 作用下， 生成 [4.4]paracyclophan-1-one
  参考文献：
  名称：

  Macro Rings. XIV. Substitution Studies in the [4.4]Paracyclophane System

  摘要：

  DOI：

  10.1021/ja01545a048
• 作为产物：
  描述：

  对二甲苯二聚体 反应 2.0h， 生成 [4.4]paracyclophane
  参考文献：
  名称：

  Macro Rings. XXXIV. A Ring Expansion Route to the Higher Paracyclophanes, and Spectra-Structure Correlations of Their Derived Ketones¹

  摘要：

  DOI：

  10.1021/ja00967a010

文献信息

• Layered Compounds. LIX. Facile Syntheses and Spectral Properties of [3.3]Cyclophanes and Related Cyclophanes
  作者：Tetsuo Otsubo、Masashi Kitasawa、Soichi Misumi

  DOI：10.1246/bcsj.52.1515

  日期：1979.5

  of [3.3]cyclophanes via dithia[4.4]cyclophanes is presented. The spectra of a variety of cyclophanes were examined and compared to those of [2.2]analogues. It was concluded from the absorption spectra that the transannular π-π interactions of the cyclophanes were strongly dependent on both ring-to-ring distance and overlapping mode. From the emission spectra, it was described that cyclophanes of parallel

  介绍了一种通过二硫杂 [4.4] 环烷合成 [3.3] 环烷的简单方法。检查了各种环芳烃的光谱，并与 [2.2] 类似物的光谱进行了比较。从吸收光谱得出结论，环芳的跨环 π-π 相互作用强烈依赖于环到环的距离和重叠模式。从发射光谱可以看出，平行夹心型的环芳很容易形成正态准分子，而[2.2] 间环芳和[2.2]-和[3.3] 间对环芳形成应变的准分子，显示出明显的荧光带红移。
• Layered Compounds. LXIII. Bromination of Double- and Triple-layered Paracyclophanes
  作者：Tetsuo Otsubo、Hisanori Horita、Yosuke Koizumi、Soichi Misumi

  DOI：10.1246/bcsj.53.1677

  日期：1980.6

  n]Triple-layered paracyclophanes underwent bromination to give exclusively monobromo derivatives substituted to the inner benzene. The reactions were markedly accelerated by the transannular electronic interaction as compared to [n]- and double-layered paracyclophanes, and their enhanced reactivities were demonstrated by some competitive reactions. The relative rates of [2.2] and [3.3]systems are in reverse

  [mm][nn]三层对环芳烃进行溴化，得到专门取代内部苯的单溴衍生物。与[n]-和双层对环芳烃相比，跨环电子相互作用显着加速了反应，并且通过一些竞争反应证明了它们增强的反应性。[2.2]和[3.3]系统的相对速率对于三层和双层系列是相反的。讨论了它们的反应机理。
• Paracyclophanes: Extending the Bridges. Reactions
  作者：Zissis Pechlivanidis、Henning Hopf、Jörg Grunenberg、Ludger Ernst

  DOI：10.1002/ejoc.200800748

  日期：2009.1

  n]Paracyclophanes with bridges of equal and unequal length (m,n ≤ 4) undergo electrophilic aromatic substitution (Friedel–Crafts acylation, bromination) under very mild conditions as long as the bridge contains less than four atoms. Whenever there is a choice, the aromatic ring is attacked at the position closest to the shorter alkano bridge, which indicates that the transannular benzene moiety acts as

  [mn]具有等长和不等长桥（m，n ≤ 4）的对环芳烃在非常温和的条件下进行亲电芳香取代（弗里德尔-克拉夫茨酰化，溴化），只要桥包含少于四个原子。每当有选择时，芳环就会在最靠近较短链烷烃桥的位置受到攻击，这表明跨环苯部分充当相邻基团。通过溴化获得的乙酰基衍生物和由其衍生的酸和酯，将第二个取代基引入到假偶合位置，即直接与导向基团相对。然而，这种效应仅在那些相邻桥的长度不超过三个原子的[mn]phanes 中观察到。对于丁醇桥接衍生物，区域选择性完全丧失。对于在一个苯环上带有两个酯取代基的 [mn] 对环芳，观察到非常相似的结果，限制情况是 [4.3] 对环芳衍生物。我们建议取代基的立体控制效应只能在环内距离低于 4 A 时发生。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• [3.3]- AND [4.4]-TROPYRIOPARACYCLOPHANE TETRAFLUOROBORATES—INTRAMOLECULAR CHARGE–TRANSFER INTERACTION—
  作者：Hisanori Horita、Tetsuo Otsubo、Soichi Misumi

  DOI：10.1246/cl.1978.807

  日期：1978.7.5

  The title compounds were synthesized and their structures were confirmed by NMR spectra. The [3.3]cyclophane 2 shows significant charge-transfer bands in its electronic spectrum. The intramolecular CT interaction in three [n.n]tropylioparacyclophane homologues is compared.

  合成了标题化合物并通过核磁共振谱确认了它们的结构。[3.3] 环芳烷 2 在其电子光谱中显示出显着的电荷转移带。比较了三个 [nn]tropylioparacyclophane 同系物的分子内 CT 相互作用。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cr: Org.Verb., 1.6.1.2.7, page 258 - 289
  作者：

  DOI：——

  日期：——