Decamethylbiphenyl | 18356-20-2

• 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: Decamethylbiphenyl
• 英文别名: 1,2,3,4,5-pentamethyl-6-(2,3,4,5,6-pentamethylphenyl)benzene
• CAS: 18356-20-2
• 化学式: C₂₂H₃₀
• 分子量: 294.48
• InChiKey: ZJSSKWZXTGHNRY-UHFFFAOYSA-N

物化性质

• 熔点：
  252.5-254.5 °C
• 沸点：
  363.9±37.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  22
• 可旋转键数：
  1
• 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

• 作为反应物：
  描述：

  Decamethylbiphenyl 在 氯 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以7.4%的产率得到decacis(dichloromethyl)biphenyl-THF solvate
  参考文献：
  名称：

  Structure, resolution, and racemization of decakis(dichloromethyl)biphenyl

  摘要：

  DOI：

  10.1021/ja00214a042
• 作为产物：
  描述：

  五甲基碘苯 在 铜 作用下， 生成 Decamethylbiphenyl
  参考文献：
  名称：

  用发烟硝酸硝化十甲基联苯和 2,3,5,6-Pentamethyl-2',3',4',5',6'-pentachlorobiphenyl。侧链攻击的 ExclusiveOrthoOrientation

  摘要：

  研究了通过标题化合物与发烟硝酸在二氯甲烷中反应获得的产物。十甲基联苯得到 6,6'-双(硝基氧基甲基)-2,2',3,3',4,4',5,5'-八甲基联苯或 2,6,6'-三(硝基氧基甲基)-2',3 ,3',4,4',5,5'-七甲基联苯为主要产物，取决于硝化剂的用量。2,3,4,5,6-Pentamethyl-2',3',4',5',6'-五氯联苯同样得到 6-nitrooxymethyl-2,3,4,5-tetramethyl-2',3', 4',5',6'-五氯联苯或2,6-双(硝基氧基甲基)-3,4.5-三甲基-2',3',4',5',6'-五氯联苯。已经提出了对联苯系统的烷基侧链进行排他性邻位攻击的一些合理的反应序列。

  DOI：

  10.1246/bcsj.47.2260

文献信息

• 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。
• Conformational shift by mutual steric interactions between two multiarmed units
  作者：Naama Zuaretz、Oren Golan、Silvio Biali

  DOI：10.1021/jo00007a035

  日期：1991.3

  Decakis(bromomethyl)biphenyl (3) has been prepared by reaction of decamethylbiphenyl with Br2/CCl4 in the presence of tetrabutylammonium bromide as catalyst. The attempted synthesis of decakis(bromomethyl)benzophenone resulted only in bromopentakis(bromomethyl)benzene (8). X-ray diffraction of a single crystal of 3 shows that the preferred conformation of 3 is not the alternate ''up-down'' conformation observed for the parent hexakis(bromomethyl)benzene, but a conformation in which the up-down alternation of the CH2Br groups is disrupted at the meta-para position of each ring. MM(85) calculations on 3 indicate that some conformations with disrupted ''up-down'' alternation of the CH2Br groups are favored over the all-alternate up-down form. It is suggested that this conformational shift is the result of the mutual steric interactions between arms of different moieties, and that syn interactions between m- and p-CH2Br groups operate in order to avoid bromine contacts between ortho groups at different rings. The barrier for Ar-CH2Br rotation was estimated from dynamic NMR data as 12.5 kcal mol-1.
• Studies on the Polymethylbenzenes. X. Reaction with Aromatic Diazonium Compounds¹
  作者：Lee Irvin Smith、Joseph H. Paden

  DOI：10.1021/ja01325a055

  日期：1934.10
• Adonin; Ryabinin; Starichenko, Russian Journal of Organic Chemistry, 1998, vol. 34, # 2, p. 286 - 287
  作者：Adonin、Ryabinin、Starichenko

  DOI：——

  日期：——
• Mokrousov,B.I. et al., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 1575 - 1578
  作者：Mokrousov,B.I. et al.

  DOI：——

  日期：——