tetra(3,3',3'',3'''-tetramethylbenzo)-1,2,3,4,5,6,7,8-naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: tetra(3,3',3'',3'''-tetramethylbenzo)-1,2,3,4,5,6,7,8-naphthalene
• 英文别名: 5,10,18,23-Tetramethylhexacyclo[12.12.0.02,7.08,13.015,20.021,26]hexacosa-1(14),2(7),3,5,8(13),9,11,15(20),16,18,21(26),22,24-tridecaene；5,10,18,23-tetramethylhexacyclo[12.12.0.02,7.08,13.015,20.021,26]hexacosa-1(14),2(7),3,5,8(13),9,11,15(20),16,18,21(26),22,24-tridecaene
• 化学式: C₃₀H₂₄
• 分子量: 384.521
• InChiKey: PVMGZNGBSRHDSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1-甲基-4-[1,2,2-三(4-甲基苯基)乙烯基]苯 在 甲烷磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到tetra(3,3',3'',3'''-tetramethylbenzo)-1,2,3,4,5,6,7,8-naphthalene
  参考文献：
  名称：

  Sequential Oxidative Transformation of Tetraarylethylenes to 9,10-Diarylphenanthrenes and Dibenzo[g,p]chrysenes using DDQ as an Oxidant

  摘要：

  Tetraarylethylenes can be sequentially transformed into 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using 1 and 2 equiv of DDQ, respectively, in CH(2)Cl(2) containing methanesulfonic acid, in excellent yields. Efficient access to substituted dibenzochrysenes from tetraarylethylenes establishes the versatility of this procedure over the existing multistep syntheses of dibenzochrysenes. Moreover, the ready regeneration of DIM from easily recovered reduced DDQ-H(2) continues to advance the use of DDQ/H(+) for the oxidative C-C bond forming reactions.

  DOI：

  10.1021/ol200069c

文献信息

• ENDOR and EPR studies on polycyclic aromatic radical cations
  作者：Hong Sang、Hanqing Wang、K. P. Such、F. Jent

  DOI：10.1002/mrc.1260300211

  日期：1992.2

  Several polycyclic aromatic radical cations produced in Friedel–Crafts alkylation reactions were studied by EPR and ENDOR methods, and the following were identified: 1,2,5,6‐tetramethylanthracene, 2,3,6,7,9,10‐hexamethylanthracene, 3,6,11,14‐tetramethyldibenzo [a,c]triphenylene and 2,6,9,10‐tetramethylanthracene radical cations.

  通过 EPR 和 ENDOR 方法研究了 Friedel-Crafts 烷基化反应中产生的几种多环芳族自由基阳离子，并确定了以下物质：1,2,5,6-四甲基蒽，2,3,6,7,9,10-六甲基蒽， 3,6,11,14-四甲基二苯并[a,c]三亚苯基和2,6,9,10-四甲基蒽自由基阳离子。
• Sakaino; Sugawara; Terao, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1996, vol. 276-277, # pt 1-2, p. 271 - 275
  作者：Sakaino、Sugawara、Terao、Fujiwara、Mori、Maeda

  DOI：——

  日期：——
• Sequential Oxidative Transformation of Tetraarylethylenes to 9,10-Diarylphenanthrenes and Dibenzo[<i>g</i>,<i>p</i>]chrysenes using DDQ as an Oxidant
  作者：Tushar S. Navale、Khushabu Thakur、Rajendra Rathore

  DOI：10.1021/ol200069c

  日期：2011.4.1

  Tetraarylethylenes can be sequentially transformed into 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using 1 and 2 equiv of DDQ, respectively, in CH(2)Cl(2) containing methanesulfonic acid, in excellent yields. Efficient access to substituted dibenzochrysenes from tetraarylethylenes establishes the versatility of this procedure over the existing multistep syntheses of dibenzochrysenes. Moreover, the ready regeneration of DIM from easily recovered reduced DDQ-H(2) continues to advance the use of DDQ/H(+) for the oxidative C-C bond forming reactions.