1,2,3,4,5,6,7,8-octamethylanthracene | 64094-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,2,3,4,5,6,7,8-octamethylanthracene
• 英文别名: octamethylanthracene；1,2,3,4,5,6,7,8-octamethyl-anthracene；1,2,3,4,5,6,7,8-Octamethyl-anthracen；Anthracene, 1,2,3,4,5,6,7,8-octamethyl-
• CAS: 64094-28-6
• 化学式: C₂₂H₂₆
• 分子量: 290.448
• InChiKey: BVRXMNBGXAEBOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1,2,3,4,5,6,7,8-octamethylanthracene 在 triethyloxonium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到1,2,3,4,5,6,7,8-octamethylanthracene cation radical hexachloroantimonate
  参考文献：
  名称：

  结晶型芳族阳离子-自由基盐的制备和结构。六氯锑酸三乙基氧鎓作为新型（单电子）氧化剂。

  摘要：

  六氯锑酸三乙基氧鎓鎓盐[Et（3）O（+）SbCl（6）（-）]是芳香族供体（ArH）的选择性氧化剂，它可以方便地制备和分离结晶顺磁性盐[ArH（+）（*） ，SbCl（6）（-）]用于各种芳香族阳离子自由基的X射线结构测定。Meerwein盐[Et（3）O（+）SbCl（6）（-）]和纯路易斯酸氧化剂SbCl（5）之间的机理关系基于离子对内先前从氧到氯的乙基转移。

  DOI：

  10.1021/jo980407a
• 作为产物：
  描述：

  五甲基苯 在 thallium(III) trifluoroacetate 作用下， 以 三氟乙酸 为溶剂， 生成 1,2,3,4,5,6,7,8-octamethylanthracene
  参考文献：
  名称：

  Photochemical Nitration by Tetranitromethane. Part XXXIV. The Photochemical Reactions of Pentamethylbenzene and Hexamethylbenzene with Tetranitromethane. The Formation and Rearrangement of Labile Adducts from Pentamethylbenzene.

  摘要：

  The photolysis of the charge transfer (CT) complex of tetranitromethane and pentamethylbenzene (13) in dichloromethane at -50 or -78 degrees C gives the labile epimeric 1,2,3,4,6-pentamethyl-3-nitro-6-trinitromethylcyclohexa-1,4-dienes 18 and 19. Adduct 18 rearranges rapidly in [H-2(2)]dichloromethane at 22 degrees C (half-life 9 min) to give 2,3,4,5-tetramethyl-1-(2',2',2'-trinitroethyl)benzene (21), 2,3,4,5-tetramethylphenylnitromethane (26), 2,3,4,5-tetramethylbenzyl nitrate (32) and 2,3,4,5-tetramethylbenzyl nitrite (36). The photolysis of the tetranitromethane-13 CT complex in dichloromethane at 20 degrees C gives compounds 21, 26, 32 and 36, in addition to their 2,3,4,6-tetramethyl analogues 20, 25, 31 and 35, the latter set of products probably arising from the rearrangement of the highly labile epimeric 1,2,3,5,6-pentamethyl-3-nitro-6-trinitromethylcyclohexa-1,4-dienes 54. The photolysis of the tetranitromethane-13 CT complex in acetonitrile gives mainly the phenylnitromethane 26, while similar reaction in 1,1,1,3,3,3-hexafluoropropan-2-ol yields pentamethylnitrobenzene 24, the latter by a nitrosation/oxidation sequence. Reaction of 13 with nitrogen dioxide in dichloromethane gives mainly compounds 26 and 30.No adducts were detected in the photolysis of the CT complex of hexamethylbenzene 14 in dichloromethane at accessible reaction temperatures (greater than or equal to-20 degrees C), but products of side-chain modification 37-46 were formed. In acetonitrile similar reaction gave in addition to the above products 37-46 the N-nitrosoacetamide 47 and its precursor 49. Compounds 47 and 49 are also formed, along with the major products pentamethylbenzyl nitrate 39 and the mono- and di-nitromethyl compounds 40 and 43, on reaction of 14 with nitrogen dioxide in acetonitrile.EPR spectroscopic examination of the photolysis of acidic (trifluoroacetic ) solutions of tetranitromethane and 13 or 14 demonstrated the formation of the corresponding radical cation or a transformation product thereof, i.e. the 1,2,3,4,5,6,7,8-octamethylanthracene radical cation from 13 or 14(.+) from 14.

  DOI：

  10.3891/acta.chem.scand.50-1121

文献信息

• Substituent Effect on Regioselectivity in Oxygenation of Multisubstituted Acenes
  作者：Xin Zhou、Masanori Kitamura、Baojian Shen、Kiyohiko Nakajima、Tamotsu Takahashi

  DOI：10.1246/cl.2004.410

  日期：2004.4

  Reaction of substituted acenes such as anthracene, naphthacene, and pentacene derivatives with O 2 was dependent on the substituents and their positions. The orientation is in contrast to Diels-Alder reaction with DDQ in the case of naphthacene and pentacene derivatives. 1,2,3,4,5,6,7,8-Octamethylanthracene reacted with O 2 to afford a doubly oxygenated compound (diendoperoxide) at both end rings.

  取代并苯如蒽、并四苯和并五苯衍生物与O 2 的反应取决于取代基及其位置。在并四苯和并五苯衍生物的情况下，该方向与 DDQ 的 Diels-Alder 反应相反。1,2,3,4,5,6,7,8-八甲基蒽与O 2 反应以在两个端环处提供双氧化化合物（二内过氧化物）。
• π-Bonded molecular wires: self-assembly of mixed-valence cation-radical stacks within the nanochannels formed by inert tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anions
  作者：Sergiy V. Rosokha、Charlotte L. Stern、Jeremy T. Ritzert

  DOI：10.1039/c3ce41719k

  日期：——

  A series of mixed-valence cation-radical salts D(n+1) TFPBn, where D is a planar organic donor of about 0.7 to 0.9 nm wide and 1.1 to 1.3 nm long (e.g., tetramethyltetraselenafulvalene, octamethylanthracene, octamethylbiphenylene, perylene) and TFPB is a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anion, were crystallized and characterized via single-crystal X-ray analyses and UV–vis-NIR-IR measurements

  一系列混合价阳离子自由基盐D （n +1） TFPB n，其中D是约0.7至0.9 nm宽，1.1至1.3 nm长的平面有机供体（例如，四甲基四硒富勒烯，八甲基蒽，八甲基联苯，per ）和TFPB是四[3,5-双（三氟甲基）苯基]硼酸盐阴离子，进行了结晶化和表征通过单晶X射线分析和UV-vis-NIR-IR测量。所有这些盐都显示了位于由庞大的惰性阴离子形成的纳米通道内的π堆叠的部分氧化的供体的一维阵列（由于平面有机阳离子自由基及其母体分子的自组装而产生）。π堆内基本平行的烃部分以〜3.4–3.6Å的平面间距分布。由于混合价阵列中的分子间相互作用，所有这些盐在NIR至IR范围（8000–1500 cm -1）中均显示出强烈的吸收带）具有低HOMO / LUMO间隙的导电有机材料的特性。量子力学计算提供了介于0.1 eV至0.3 eV之间的相邻物种之间的电子耦合元件。这些值大于用于电子转移的相
• Formation of the radical cation of 1,2,3,4,5,6,7,8-octamethylanthracene from bis(pentamethylphenyl)methane in trifluoroacetic acid
  作者：Lennart Eberson、Finn Radner

  DOI：10.1039/c39910001233

  日期：——

  The radical cation formed upon dissolution of bis(pentamethylphenyl)methane in trifluoroacetic acid has been shown to be that of 1,2,3,4,5,6,7,8-octamethylanthracene.

  已经表明，双（五甲基苯基）甲烷溶解在三氟乙酸中形成的自由基阳离子是1,2,3,4,5,6,7,8-八甲基蒽的自由基阳离子。
• An ESR and ENDOR study of the octamethylanthracene radical cation generated from methylarylstannanes and -germanes
  作者：Manfred Lehnig、Thomas Reiche、Susanne Reiss

  DOI：10.1016/s0040-4039(00)74675-2

  日期：1992.7

  The radical cation of 1,2,3,4,5,6,7,8-octamethylanthracene 1 is formed by a Friedel-Crafts reaction of hexakis-(pentamethylphenyl)distannane with AlCl3 in CH2Cl2 followed by a Scholl condensation and an oxidation.

  1,2,3,4,5,6,7,8-八甲基蒽1的自由基阳离子是通过六烷基-（五甲基苯基）二锡与AlCl 3在CH 2 Cl 2中的Friedel-Crafts反应形成的，然后进行Scholl缩合反应和氧化。
• Deoxygenation of arene 1,4-endoxides with low-valent metals
  作者：Harold Hart、Godson Nwokogu

  DOI：10.1021/jo00320a005

  日期：1981.3