1,2-二对甲苯基乙烷 | 538-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-二对甲苯基乙烷
• 中文别名: 1,2-二(对甲苯)乙烷
• 英文名称: 1,2-di-p-tolylethane
• 英文别名: 1,2-bis(4-methylphenyl)ethane；4,4'-dimethylbibenzyl；4,4’-dimethylbibenzyl；1-methyl-4-[2-(4-methylphenyl)ethyl]benzene
• CAS: 538-39-6
• 化学式: C₁₆H₁₈
• mdl: MFCD00026025
• 分子量: 210.319
• InChiKey: XCCQFUHBIRHLQT-UHFFFAOYSA-N

物化性质

• 熔点：
  80-83 °C(lit.)
• 沸点：
  178 °C(lit.)
• 密度：
  0.9761 (estimate)
• 闪点：
  296-298°C/730mm
• 溶解度：
  可溶于酒精

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36/37
• 危险类别码：
  R22
• 海关编码：
  2902909090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1,2-二对甲苯基乙烷 在 Cs/Na/K alloy 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以225 mg的产率得到1-(2,5-dihydro-4-methylphenyl)-2-p-tolylethane
  参考文献：
  名称：

  Carbanions. 23. Cleavages of 1,2-diphenylethane and derivatives by cesium-potassium-sodium alloy. Competitive rates of bond scission

  摘要：

  DOI：

  10.1021/ja00358a018
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 在 4,4'-二叔丁基苯并 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以49%的产率得到1,2-二对甲苯基乙烷
  参考文献：
  名称：

  脱氧/还原芳族酯，α二酮类，偶姻类，和环氧化物的，以相应的联苄产物与锂4,4'-二吨-butylbiphenyl阴离子自由基

  摘要：

  芳族酯，苯偶酰，苯偶姻，超声处理顺和-反式-芪，和反式与在催化量的4,4'-二-的存在过量的锂芪氧化物吨-butylbiphenyl（DBB）在无水THF，得到联苄的衍生物高产。

  DOI：

  10.1016/s0040-4039(01)80546-3

文献信息

• Etude du Comportement Photochimique de quelques Diaryl-1,3-triazènes
  作者：Par Michel Julliard、Gaston Vernin、Jacques Metzger

  DOI：10.1002/hlca.19800630216

  日期：1980.3.5

  Study of the Photochemical Behaviour of Some Diaryl-1,3-triazenes

  某些二芳基-1,3-三氮烯的光化学行为研究
• “Bulky-Yet-Flexible” α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air
  作者：Xu-Wen Yang、Dong-Hui Li、A-Xiang Song、Feng-Shou Liu

  DOI：10.1021/acs.joc.0c01509

  日期：2020.9.18

  regioselective and efficient reductive Heck reaction, a series of moisture- and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the“bulky-yet-flexible”palladium complexes allowed highly anti-Markovnikov-selective

  为了进行高度区域选择性和高效的还原性Heck反应，合理设计，易于合成和充分表征了一系列湿气和空气稳定的α-二亚胺钯预催化剂。研究了钯配合物的结构与催化性能之间的关系。揭示了“大而尚柔的”钯配合物在好氧条件下可以使烯烃与（杂）芳基溴化物高度抗马尔科夫尼科夫选择性加氢芳基化。本方案的进一步合成应用可以提供对功能和生物活性分子的快速直接访问。
• Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols
  作者：Xing-Zhong Shu、Feng-Feng Pan、Peng Guo、Xiaochuang Huang

  DOI：10.1055/a-1467-2432

  日期：2021.9

  blocks that are widely used in organic synthesis, and they are typically prepared by the homocoupling of halides, organometallics, and ethers. Herein, we report an approach to this class of compounds using alcohols, which are more stable and readily available. The reaction proceeds via nickel-catalyzed and dimethyl oxalate assisted dynamic kinetic homocoupling of benzyl alcohols. Both primary and secondary

  二苄基是广泛用于有机合成中的基本结构单元，它们通常通过卤化物，有机金属和醚的均偶联来制备。本文中，我们报告了一种使用醇的这类化合物的方法，该醇更稳定且易于获得。该反应通过镍催化的和草酸二甲酯辅助的苄醇的动态动力学均偶联进行。伯醇和仲醇都是可以容忍的。
• Flash vacuum pyrolysis over magnesium. Part 1. Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides
  作者：R. Alan Aitken、Philip K. G. Hodgson、John J. Morrison、Adebayo O. Oyewale

  DOI：10.1039/b108663d

  日期：2002.1.23

  Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E,E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

  在玻璃棉上覆盖一层新升华的镁,进行闪式真空热解,能有效促使苄基卤化物耦合生成相应的联苄。当有邻位卤素取代基存在时,进一步脱卤生成部分二氢蒽和蒽。卤甲基萘和二苯基甲烷也能高效耦合,而三苯基氯甲烷则生成4,4′-双(二苯甲基)联苯。用α,α′-二卤代邻二甲苯可以获得较高产率的苯并环丁烯,而异构的α,α′-二卤代对二甲苯,通过形成的对二甲苯的聚合,可以得到一系列高热稳定性的聚合物。其他卤代烃苯大体上会脱卤化氢,某些情况下能产生环化反应。同样可以观察到,苯基卤代烷烃脱去羰基生成苯乙炔以及其他产物。简单的烷基卤化物则高效地脱去HCl或HBr生成烯烃。脂肪族二卤化物也会发生这一反应生成二烯,但不发生环化反应生成环烷烃,或在某些情况下发生氢原子转移的脱卤反应生成烯烃。5-溴戊-1-烯的产物符合自由基途径的预期,但6-溴己-1-烯并不符合。2,2-二氯丙烷和1,1-二氯丙烷能脱去HCl,但1,1-二氯丁烷、戊烷和己烷则能部分水解,随后脱去HCl,生成E,E-, E,Z-和Z,Z-异构体二烷-1-烯基醚,并且得到了这些物质的13C NMR全归属数据。6-氯己-1-炔和7-氯庚-1-炔能发生环化反应生成亚甲基环烷烃和环炔烃。本文还考察了1,2-二溴环己烷和1,2-二氯环辛烷在上述条件下的行为。本文给出了众多种证据,表明这些反应过程不涉及气相自由基的形成,而是表面吸附的金属有机物种。
• Nickel catalyzed deoxygenative cross-coupling of benzyl alcohols with aryl-bromides
  作者：Vinoth Kumar Chenniappan、Devin Peck、Ronald Rahaim

  DOI：10.1016/j.tetlet.2020.151729

  日期：2020.4

  nickel-catalyzed cross-electrophile coupling of benzyl alcohols with aromatic bromides has been developed. This deoxygenative cross-coupling occurs under mild reaction conditions at ambient temperature affording diarylmethanes, or 1,3-diarylpropenes from benzyl allyl alcohols. The system demonstrated good chemoselectivity tolerating an assortment of reactive functional groups.

  已经开发了镍催化的苄醇与芳族溴化物的亲电子交联。该脱氧交叉偶联在环境温度下在温和的反应条件下发生，从苄基烯丙醇得到二芳基甲烷或1，3-二芳基丙烯。该系统表现出良好的化学选择性，可耐受各种反应性官能团。

表征谱图