(3-methylphenyl)diphenylmethane | 603-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3-methylphenyl)diphenylmethane
• 英文别名: m-Tolyl-diphenyl-methan；1-benzhydryl-3-methylbenzene
• CAS: 603-26-9
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: WVENNCSCPHNMHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  354.0±0.0 °C(Predicted)
• 密度：
  1.0072 g/cm3(Temp: 90 °C)
• 熔点：
  60.2 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (3-methylphenyl)diphenylmethane 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 Diphenyl-m-tolyl-carbinol
  参考文献：
  名称：

  Bistrzycki; Gyr, Chemische Berichte, 1904, vol. 37, p. 1250

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 barium dihydroxide 作用下， 生成 (3-methylphenyl)diphenylmethane
  参考文献：
  名称：

  Hemilian, Chemische Berichte, 1883, vol. 16, p. 2361

  摘要：

  DOI：

文献信息

• NiXantphos: A Deprotonatable Ligand for Room-Temperature Palladium-Catalyzed Cross-Couplings of Aryl Chlorides
  作者：Jiadi Zhang、Ana Bellomo、Nisalak Trongsiriwat、Tiezheng Jia、Patrick J. Carroll、Spencer D. Dreher、Matthew T. Tudge、Haolin Yin、Jerome R. Robinson、Eric J. Schelter、Patrick J. Walsh

  DOI：10.1021/ja411855d

  日期：2014.4.30

  remarkable chemoselectivity in the presence of aryl chloride substrates bearing heteroaryl groups and sensitive functional groups that are known to undergo 1,2-addition, aldol reaction, and O-, N-, enolate-α-, and C(sp2)–H arylations. The advantages and importance of the Pd–NiXantphos catalyst system outlined herein make it a valuable contribution for applications in Pd-catalyzed arylation reactions with

  尽管过去 15 年见证了用于钯催化与芳基氯化物交叉偶联的空间庞大且富含电子的烷基膦配体的发展，但基于三芳基膦或双齿膦配体的钯催化剂实例可用于与芳基氯化物进行有效的室温交叉偶联反应未活化的芳基氯化物很少见。在此，我们报告了一种基于 NiXantphos 的钯催化剂，一种可去质子化的螯合芳基二膦配体，可在室温下氧化添加未活化的芳基氯化物。令人惊讶的是，大量配体的比较表明，在碱性反应条件下，所得的异双金属 Pd-NiXantphos 催化剂体系在去质子交叉偶联过程 (DCCP) 与芳基氯中优于所有其他单齿和双齿配体。带有芳基氯的 DCCP 可提供多种三芳基甲烷产品，这是一类具有多种应用和有趣生物活性的化合物。此外，DCCP 在带有杂芳基和敏感官能团的芳基氯底物存在下表现出显着的化学选择性，这些官能团已知会发生 1,2-加成、羟醛反应和 O-、N-、烯醇化物-α-和 C( sp2)–H 芳基化。本文概述的
• 1,2-Sulphur shift in the acid-catalysed cyclisation of o-arylthiophenyl-substituted carbinols to thioxanthen derivatives
  作者：Giuseppe Capozzi、Giovanni Melloni、Giorgio Modena

  DOI：10.1039/p19730002250

  日期：——

  During the acid-catalysed cyclisation of some o-arylthiophenyl-substituted carbinols to thioxanthen derivatives, arearrangement was observed with carbinols having a para-methyl substituentin thearylthio-group. Thus, 1-[o-(p-tolylthio)phenyl]ethanol gave 3,9-dimethylthioxanthen, while α-[o-(p-tolylthio)phenyl]benzyl alcohol gave a mixture of 3-methyl- and 2-methyl-9-phenylthioxanthen. The mechanism

  在一些邻-芳基硫基苯基取代的甲醇的酸催化环化为噻吨酮衍生物的过程中，观察到芳基硫基中具有对甲基取代基的甲醇的排列。因此，1- [邻-（对甲苯硫基）苯基]乙醇给出了3,9-二甲基噻吨，而α-[邻-（对甲苯硫基）苯基]苄醇得到了3-甲基-和2-甲基-的混合物。 9-苯基噻吨。环化的机理在位置闭环之间的竞争方面所讨论的邻位的硫（邻闭环3'-取代），并且在位置带有硫接着是1,2-硫移（ipso -substitution）。
• Fischer,E.; Fischer,O., Justus Liebigs Annalen der Chemie, 1878, vol. 194, p. 290;
  作者：Fischer,E.、Fischer,O.

  DOI：——

  日期：——
• Detailed Characterization of <i>p</i>-Toluenesulfonic Acid Monohydrate as a Convenient, Recoverable, Safe, and Selective Catalyst for Alkylation of the Aromatic Nucleus
  作者：Mathew P. D. Mahindaratne、Kandatege Wimalasena

  DOI：10.1021/jo971832r

  日期：1998.5.1

  Alkylation of the aromatic nucleus, an important reaction in industry and synthetic organic chemistry, has traditionally been carried out by the well-known Friedel-Crafts reaction employing Lewis acid catalysts such as AlCl3 and BF3 or by using highly reactive organometallic reagents. Although protic acids such as anhydrous HF and concentrated H2SO4 have also been used in the alkylation of the aromatic nucleus, the notoriously corrosive, highly toxic, and hazardous nature of these agents has precluded their common use under ordinary laboratory conditions. Various organic sulfonic acids have, on occasion, been used as catalysts in Friedel-Crafts alkylations, but to our knowledge the chemistry and the scope of these reactions for common laboratory use have never been exploited in detail. In the present study we have characterized commercially available p-toluenesulfonic acid monohydrate (TsOH) as an efficient catalyst for the intermolecular coupling of the aromatic nucleus with activated alkyl halides, alkenes, or tosylates under mild conditions in an open atmosphere. In comparison to conventional Friedel-Crafts catalysts such as AlCl3, BF3, HF, and concentrated H2SO4, the extent of the formation of undesired products from side reactions such as transalkylation, polymerization, etc. was minimal with the TsOH-catalyzed reaction. The ability to recover and reuse the catalyst from the reaction mixtures, minimal generation of environmentally unfriendly waste, high specificity of the reaction, and the low cost of the catalyst are important advantages of the TsOH catalyst over the other conventional Friedel-Crafts catalysts.
• LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature
  作者：Xinfei Ji、Tao Huang、Wei Wu、Fang Liang、Song Cao

  DOI：10.1021/acs.orglett.5b02602

  日期：2015.10.16

  A practical and convenient approach for the secondary C(sp(3))-H arylation of diarylmethanes with various fluoroarenes is described. The reaction proceeds smoothly in the presence of LDA (lithium diisopropylamide) at room temperature and affords triarylmethanes in moderate to high yields.