2-methyldibenzo[g,p]chrysene | 1274702-42-9

• 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: 2-methyldibenzo[g,p]chrysene
• 英文别名: 5-Methylhexacyclo[12.12.0.02,7.08,13.015,20.021,26]hexacosa-1(14),2(7),3,5,8,10,12,15,17,19,21,23,25-tridecaene
• CAS: 1274702-42-9
• 化学式: C₂₇H₁₈
• 分子量: 342.44
• InChiKey: DPAPVNUMIUJARL-UHFFFAOYSA-N

物化性质

• 沸点：
  612.9±22.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 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-(4-甲基苯基)-1,2,2-三苯乙烯 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 9.5h， 生成 2-methyldibenzo[g,p]chrysene
  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

• Catalyst-Free Intramolecular Formal Carbon Insertion into σ-CC Bonds: A New Approach toward Phenanthrols and Naphthols
  作者：Ying Xia、Peiyuan Qu、Zhenxing Liu、Rui Ge、Qing Xiao、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201209269

  日期：2013.2.25

  of carbonyl groups in keto aldehyde substrates has been exploited for the synthesis of phenanthrols, naphthols, and their heteroatom‐containing analogues. Key to this highly efficient and robust methodology is the catalyst‐free intramolecular formal diazo carbon insertion of N‐tosylhydrazones into keto CC bonds (see scheme).

  酮醛底物中两种羰基的不同反应性已被用于合成菲咯啉，萘酚及其含杂原子的类似物。键这一高效完善的方法是的不含催化剂的分子内正式重氮碳插入Ñ -tosylhydrazones成酮Ç  C键（参见方案）。
• Palladium-Catalyzed Annulation of 2,2′-Dibromobiphenyls with Alkynes: Synthesis of Functionalized Phenanthrenes and Dibenzochrysenes
  作者：Gaoqiang Li、Feng Xu、Jun Ma、Yan Qiao、Jingxuan Tu、Sha Liu

  DOI：10.1055/s-0034-1378726

  日期：——

  A palladium-catalyzed annulation process of 2,2′-dibromobiphenyls with alkynes for the synthesis of functionalized phenanthrenes has been realized. The methodology provides an efficient approach to dibenzochrysene derivatives starting from simple reactants in two steps.

  已经实现了钯催化的 2,2'-二溴联苯与炔烃的环化过程，用于合成功能化菲。该方法提供了一种从简单反应物开始分两步处理二苯并芘衍生物的有效方法。
• Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of <i>o</i>-Iodobiphenyls or (<i>Z</i>)-β-Halostyrenes with <i>o</i>-Bromobenzyl Alcohols through Two Sequential C–C Bond Formations Catalyzed by a Palladium Complex
  作者：Masayuki Iwasaki、Yasuhiro Araki、Shohei Iino、Yasushi Nishihara

  DOI：10.1021/acs.joc.5b01693

  日期：2015.9.18

  bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular

  邻溴苄醇已被开发为一种新型的带有亲核和亲电取代基的环化试剂，可轻松合成多环芳烃。钯/电子不足的膦催化剂有效地将邻碘联苯或（Z）-β-卤代苯乙烯与邻溴苄醇偶联，分别制得三亚苯基和菲。目前的级联反应是通过去乙酰化交叉偶联和顺序分子内环化进行的。大量实验数据表明，反应机理涉及1,4-钯迁移的平衡。
• Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with <i>o</i>-Bromobenzyl Alcohols through Multiple Carbon–Carbon Bond Formations
  作者：Masayuki Iwasaki、Yasuhiro Araki、Yasushi Nishihara

  DOI：10.1021/acs.joc.7b00848

  日期：2017.6.16

  benzannulation with o-bromobenzyl alcohols enabled the facile construction of phenanthrene skeletons via the sequential multiple carbon–carbon bond formations. A variety of multisubstituted phenanthrenes were synthesized by the reaction of (Z)-β-halostyrenes with o-bromobenzyl alcohols as well as by the three-component coupling of alkynes, aryl bromides, and o-bromobenzyl alcohols. The electron-deficient phosphine

  邻溴苄醇与钯催化的苯环合可以通过连续的多个碳-碳键形成而轻松地构建菲骨架。多种多取代菲的通过的（反应合成Ž）-β-卤代苯乙烯与ö -bromobenzyl醇以及由炔烃组成的三组分偶联，芳基溴化物和ö-溴苄醇。缺电子的膦配体在控制所用的两种不同有机卤化物的顺序氧化加成中起着重要作用，从而实现了以良好的收率选择性形成所需的菲。该合成方案也适用于高度稠合的多环芳族烃如四苯的合成。
• 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.