四环[14.2.2.24,7.210,13]二十四碳-4,6,10,12,16,18,19,21,23-九烯 | 283-80-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 四环[14.2.2.24,7.210,13]二十四碳-4,6,10,12,16,18,19,21,23-九烯
• 中文别名: 三聚对二甲苯
• 英文名称: [2.2.2]paracyclophane
• 英文别名: [2.2.2]Paracyclophan；Tricyclophane；tetracyclo[14.2.2.24,7.210,13]tetracosa-1(19),4,6,10(22),11,13(21),16(20),17,23-nonaene
• CAS: 283-80-7
• 化学式: C₂₄H₂₄
• 分子量: 312.455
• InChiKey: FDUPXAHIOFBIAE-UHFFFAOYSA-N

物化性质

• 熔点：
  161-164°C

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  四环[14.2.2.24,7.210,13]二十四碳-4,6,10,12,16,18,19,21,23-九烯 在 1,3-丙二醇 作用下， 生成 晕苯
  参考文献：
  名称：

  Mechanical analysis of the seasonal snow cover

  摘要：

  A snow model has been developed to calculate the forces and displacements of a seasonal snow cover in order to obtain information on damage caused by snow to forestry plants and technological constructions. Two components of motion may be observed in a settled snowpack: creeping (internal deformation), depending on the internal body weight, and gliding (slip of the entire snowpack over the ground), this is caused by external factors such as free water in the boundary layer or a lack of macroscopic roughness. This model is based on the simplification that the snow cover is an isotropic and homogenous material. For this application the slope is divided into quadrangular finite elements and the creeping behaviour is assigned to them. Depending on the period of model usage it was chosen between two material models: a linear viscoelastic model of snow for a shorter period of consideration and a linear viscous model of material for a longer period of consideration. Gliding is described by verifying the parameter of friction and by geometrical means of description whereby the macroscopic ground roughness is assumed to be modelled by a simple sine wave. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s1464-1909(00)00093-9
• 作为产物：
  描述：

  2,11,20-triaza<3.3.3>paracyclophane 在 盐酸 、 氢氧化钾 、 sodium disulfite 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 生成 四环[14.2.2.24,7.210,13]二十四碳-4,6,10,12,16,18,19,21,23-九烯
  参考文献：
  名称：

  [2.2]环烷的合成新方法

  摘要：

  通过氮的还原性挤出，将重氮[3.3]环环烷酮通过其N-亚硝基衍生物转化为相应的[2.2]环环烷酮。该反应简单，清洁且温和，并且可能是[2.2]环烷的另一种合成方法。

  DOI：

  10.1016/0040-4039(88)85327-9

文献信息

• Synthesis and characterisation of [Ru6C(CO)14] cluster complexes of some [2.2]- and [2.2.2]-cyclophane ligands
  作者：Paul Schooler、Brian F. G. Johnson、Laura Scaccianoce、Rosemary Tregonning

  DOI：10.1039/a903103k

  日期：——

  Some [Ru6C(CO)14] cluster complexes bearing the [2.2]ortho-, anti-[2.2]meta- and [2.2.2]para-cyclophane ligands have been prepared, isolated and characterised. The molecular structure of two new compounds [Ru6C(CO)14(meta-C16H16)] 2 and [Ru6C(CO)14(para-C24H24)] 4 have been established by X-ray diffraction studies which show that the cyclophane ligands are bound in an apical η6 mode in both cases. This is at variance with the face-capping µ3-η2∶η2∶η2 mode observed in the previously reported structure of [Ru6C(CO)14(para-C16H16)] 1. Spectroscopic evidence obtained for [Ru6C(CO)14(ortho-C16H16)] 3 suggests that the cyclophane ligand is bound in an apical η6 mode too. The synthesis of 1 via the redox coupling of [Ru5C(CO)14]2– with [Ru(η6-C16H16)(NCMe)3]2+ is presented as an alternative to the thermolysis of [Ru3(CO)12] with [2.2]paracyclophane in heptane.

  一些含有[2.2]正位、反式[2.2]中位和[2.2.2]对位环糊精配体的[Ru6C(CO)14]簇合物已被合成、分离并表征。通过X射线衍射研究确定了两个新化合物[Ru6C(CO)14(meta-C16H16)] 2和[Ru6C(CO)14(para-C24H24)] 4的分子结构，结果表明这两个环糊精配体均以顶点η6模式结合。这与之前报告的[Ru6C(CO)14(para- )] 1结构中观察到的面封闭µ3-η2∶η2∶η2模式有所不同。对[Ru6C(CO)14(ortho- )] 3的光谱证据表明，该环糊精配体也以顶点η6模式结合。通过[Ru5C(CO)14]2–与[Ru(η6- )(NCMe)3]2+的氧化还原耦合合成1被提出作为一种替代方法，取代了在庚烷中用[2.2]对位环糊精热分解[Ru3(CO)12]的方式。
• Alternative General Synthetic Routes to [2.2]Cyclophanes and [3.2]Cyclophanes from [3.3]Cyclophane-2,11-diones by Photodecarbonylation, and a Structural Study of [3.2]Metacyclophanes
  作者：Hajime Isaji、Mikio Yasutake、Hiroyuki Takemura、Katsuya Sako、Hitoshi Tatemitsu、Takahiko Inazu、Teruo Shinmyozu

  DOI：10.1002/1099-0690(200107)2001:13<2487::aid-ejoc2487>3.0.co;2-f

  日期：2001.7

  Photodecarbonylation of [3.3]cyclophane-2,11-diones, which are readily prepared by TosMIC coupling, affords [2.2]cyclophanes in high yield. This method also provides a general synthetic method for [3.2]cyclophan-2-ones by taking advantage of the fact that this photochemical reaction proceeds in a stepwise manner through [3.2]cyclophan-2-ones. A series of [2.2]cyclophanes, [3.2]cyclophanes, and [3.3]cyclophanes

  [3.3] 环烷-2,11-二酮的光脱羰，很容易通过 TosMIC 偶联制备，以高产率提供 [2.2] 环烷。该方法还利用[3.2]环芳-2-酮的光化学反应以逐步方式进行这一事实，提供了[3.2]环芳-2-酮的通用合成方法。因此，可以从常见的前体 [3.3] 环烷-2,11-二酮制备一系列 [2.2] 环烷、[3.2] 环烷和 [3.3] 环烷。与 [3.3] 环芳烃的首选顺式几何结构形成鲜明对比的是，[3.2] 环芳烃采用反几何结构，并且通过变温 1 H NMR 光谱观察到芳环反转过程。在结晶状态下，尽管桥长不对称，但反[3.2]环芳烃的两个芳环几乎平行；
• Ultraviolet Laser Desorption of Chromium Tricarbonyl Arene Complexes:  A Route to Extended Sandwich Complexes
  作者：Michael J. Dale、Paul J. Dyson、Priya Suman、Renato Zenobi

  DOI：10.1021/om960592n

  日期：1997.1.1

  desorption/ionization mass spectra of the benzene complex Cr(CO)3(C6H6) and the [2.2]cyclophane complexes Cr(CO)3(C16H16-1,4), Cr(CO)3(C16H16-1,3), and Cr(CO)3}2(C24H24) are reported. In each spectrum intense ion signals are obtained which correspond to the decarbonylated chromium arene cation [Cr(arene)]+ and the bis(arene) sandwich cation [Cr(arene)2]+. The cyclophane complexes also generate ion signals at higher

  苯配合物Cr（CO）3（C 6 H 6）和[2.2]环烷配合物Cr（CO）3（C 16 H 16 -1,4），Cr的正离子紫外激光解吸/电离质谱报告了（CO）3（C 16 H 16 -1,3）和Cr（CO）3 } 2（C 24 H 24）。在每个光谱中，获得对应于脱羰基铬芳烃阳离子[Cr（arene）] +和双（芳烃）夹心阳离子[Cr（arene）2 ] +的强离子信号。环烷配合物还产生更高质量的离子信号，这可归因于扩展的多核夹心复合物。另外，Cr（CO）6和[2.2]对环环烷的混合物的紫外激光解吸质谱显示包含含有新的金属-配体键的离子，即。夹心物质[Cr（C 16 H 16 -1,4）2 ] +。
• Paracyclophanes as Versatile <i>π</i>-Donor Ligands Directing Formation of Extended Organometallic Networks
  作者：Marina A. Petrukhina、Alexander S. Filatov、Yulia Sevryugina、Kristian W. Andreini、Satoshi Takamizawa

  DOI：10.1021/om051100m

  日期：2006.4.1

  has been used. As a result, a product with Rh2:L2 = 1:1 composition (1) has been obtained from the reaction of dirhodium(II,II) tetrakis(trifluoroacetate) with [2.2]paracyclophane (L2 = C16H16). Complex 1 consists of alternating dimetal units and [2.2]paracyclophane bridges that form 1-D organometallic chains:  [Rh2(O2CCF3)4·(μ2-η2:η2-C16H16)]1∞. In the case of [2.2.2]paracyclophane (L3 = C24H24)

  研究了含有两个和三个苯环的多齿非平面芳族配体的配位性质，即[2.2]-和[2.2.2]对环环烷。气相沉积方法已用于检查无溶剂环境中的金属-π相互作用，以及制备结晶形式的对环烷配体的有机金属π-络合物。为了强制对环烷的桥接模式并实现扩展的有机金属组装体的形成，已经使用了具有两个路易斯酸性中心，即[Rh 2（O 2 CCF 3）4 ]的双核金属配合物。结果，具有Rh 2：L 2的产物从四（三氟乙酸）二吡啶鎓（II，II）与[2.2]对环环烷（L 2＝ C 16 H 16）的反应获得＝ 1∶1的组合物（1）。复杂1由交替的双金属单元和[2.2]对环芳烷桥这种形式1-d的有机金属链：的[Rh 2（O 2 CCF 3）4 ·（μ 2 - η 2：η 2 -C 16 ħ 16）] 1 ∞。在[2.2.2]对环环烷的情况下（L 3 = C 24 H在图24中，已经以结晶形式制备了化学计量比为Rh 2：L
• Exploring the Chemistry of [2.2.2]Paracyclophane
  作者：Henning Hopf、Verena Lehne、Ludger Ernst

  DOI：10.1055/s-0035-1561483

  日期：——

  Starting with the parent compound [2.2.2]paracyclophane several routes were developed to synthesize its 4-vinyl derivative. From the 4-aldehyde and the bromomethyl derivative the stilbenophanes were prepared which photocyclize to the phenanthrenophanes. A new route to a bridged ketone was developed which was subjected to the addition of phenyllithium and to typical aromatic substitution reactions (inter

  从母体化合物 [2.2.2] 对环芳开始，开发了几种合成其 4-乙烯基衍生物的路线。由4-醛和溴甲基衍生物制备芪酚，其光环化为菲酚。开发了一种新的桥接酮路线，该路线经历了苯基锂的加成和典型的芳香族取代反应（尤其是里什甲酰化、弗里德尔-克拉夫茨酰化）。桥接酮的溴化产生了一种不寻常的托酮衍生物。还对桥连烃（桥连酮的还原产物）进行了亲电取代反应。对于桥连酮和桥连烃，亲电取代发生区域选择性，有利于分别以顺式方向​​将新取代基引入桥接酮基和亚甲基基团。1 引言 2 结果与讨论 2.1 4-乙烯基[2.2.2] 对环烷 (5) 2.2 [2.2.2] 对环烷 (2a) 作为扩展芳烃系统的一部分 2.3 5,12-甲醇 [2.2.2] 对环烷的制备-25-one ( 3 ) 2.4 与 5,12-Methano[2.2.2] paracyclophan-25-one ( 3 ) 的选择性反应 2.4.1