2,2',3,3',4,4',5,6,6'-Nonamethyl-diphenylmethan | 21894-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2',3,3',4,4',5,6,6'-Nonamethyl-diphenylmethan
• 英文别名: 1,2,3,4,5-Pentamethyl-6-[(2,3,4,6-tetramethylphenyl)methyl]benzene；1,2,3,4,5-pentamethyl-6-[(2,3,4,6-tetramethylphenyl)methyl]benzene
• CAS: 21894-95-1
• 化学式: C₂₂H₃₀
• 分子量: 294.48
• InChiKey: DQPPOEXEESRRAD-UHFFFAOYSA-N

物化性质

• 熔点：
  139-141 °C
• 沸点：
  430.7±40.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  五甲基苯 在 三氟化硼乙醚 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以43%的产率得到2,2',3,3',4,4',5,6,6'-Nonamethyl-diphenylmethan
  参考文献：
  名称：

  使用高价碘（III）试剂进行烷基芳烃的新型高效氧化联芳基偶联反应

  摘要：

  已经开发出了使用高价碘（III）试剂，苯基碘（III）双（三氟乙酸盐）（PIFA）和BF 3 ·Et 2 O的组合，首先容易，有效地进行烷基芳烃的氧化偶联反应，生成烷基联芳基的方法。

  DOI：

  10.1016/s0040-4039(02)02150-0

文献信息

• Photochemical Nitration by Tetranitromethane. Part XXXIV. The Photochemical Reactions of Pentamethylbenzene and Hexamethylbenzene with Tetranitromethane. The Formation and Rearrangement of Labile Adducts from Pentamethylbenzene.
  作者：Lennart Eberson、Michael P. Hartshorn、David J. Timmerman-Vaughan、Yincai Su、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-1121

  日期：——

  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.
• Novel and efficient oxidative biaryl coupling reaction of alkylarenes using a hypervalent iodine(III) reagent
  作者：Hirofumi Tohma、Minako Iwata、Tomohiro Maegawa、Yasuyuki Kita

  DOI：10.1016/s0040-4039(02)02150-0

  日期：2002.12

  First facile and efficient oxidative coupling reaction of alkylarenes leading to alkylbiaryls using a combination of hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), and BF3·Et2O has been developed.

  已经开发出了使用高价碘（III）试剂，苯基碘（III）双（三氟乙酸盐）（PIFA）和BF 3 ·Et 2 O的组合，首先容易，有效地进行烷基芳烃的氧化偶联反应，生成烷基联芳基的方法。

表征谱图