7-甲氧基-1-(4-甲氧基苯基)-1,2-二氢萘 | 156943-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 7-甲氧基-1-(4-甲氧基苯基)-1,2-二氢萘
• 英文名称: 6-methoxy-1-(4-methoxyphenyl)-1,2-dihydronaphthalene
• 英文别名: 7-Methoxy-1-(4-methoxyphenyl)-1,2-dihydronaphthalene；7-methoxy-1-(4-methoxyphenyl)-1,2-dihydronaphthalene
• CAS: 156943-84-9
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: FWABQSFELQQYAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  390.4±42.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trans-1,2-bis(4-methoxyphenyl)cyclobutane 以 乙腈 为溶剂， 生成 7-甲氧基-1-(4-甲氧基苯基)-1,2-二氢萘
  参考文献：
  名称：

  Nanosecond and Picosecond Dynamics of the Radical Cation Mediated Dimerization of 4-Methoxystyrene

  摘要：

  The addition of the 4-methoxystyrene radical cation to neutral 4-methoxystyrene and the cleavage reactions of the 1,2-bis(4-methoxyphenyl)cyclobutane radical cation in acetonitrile have been studied by product analysis and by nanosecond and picosecond transient absorption spectroscopy. The main product upon radical cation mediated dimerization of 4-methoxystyrene using chloranil as the electron transfer sensitizer is a substituted dihydronaphthalene, 1,2-dihydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene, at low concentrations of 4-methoxystyrene. At higher concentrations, the main product is 1,2-bis(4-methoxyphenyl)cyclobutane. Cleavage of the cyclobutane radical cation is found to give 4-methoxystyrene and the dihydronaphthalene in a 1:3 ratio. In the time-resolved experiments, the radical cations are generated from 4-methoxystyrene and 1,2-bis(4-methoxyphenyl)cyclobutane by 266-nm photoionization or by 355-nm photoinduced electron transfer using triplet chloranil as the sensitizer. A transient with an absorption maximum at 500 nm is observed as a short-lived intermediate in both the radical cation mediated 4-methoxystyrene dimerization and the cyclobutane radical cation cleavage experiments. Spectroscopic and kinetic considerations lead to the conclusion that this transient is a substituted hexatriene radical cation produced as an intermediate in the conversion of the 1,2-bis(4-methoxyphenyl)cyclobutane radical cation to the dihydronaphthalene. Observed rate constants for the decay of the 4-methoxystyrene radical cation measured at 4-methoxystyrene concentrations of 0.0001 to 0.015 M increase in a linear fashion with concentration, while at concentrations >0.2 M, the observed rate constant is found to be independent of concentration. Analysis of the kinetic data according to a rate law derived from a concerted [2 + 1] mechanism leads to the following rate constants: k(1) = 1.4 X 10(9) M(-1) s(-1) for the addition reaction, k(-1) = 8 x 10(7) s(-1) for the cycloreversion reaction, k(2) = 2.5 X 10(8) s(-1) for the rearrangement of the cyclobutane radical cation, and k(3) = 1.5 X 10(10) M(-1) s(-1) for the reduction of the cyclobutane radical cation by neutral 4-methoxystyrene. Monitoring the kinetics of the reactions of the cyclobutane radical cation gives the same values for the rate constants k(2) and k(-1).

  DOI：

  10.1021/ja00094a049

文献信息

• Photocatalytic hydrogen-evolution dimerization of styrenes to synthesize 1,2-dihydro-1-arylnaphthalene derivatives using Acr+-Mes and cobaloxime catalysts
  作者：Wenxiao Cao、Chengjuan Wu、Tao Lei、Xiulong Yang、Bin Chen、Chenho Tung、Lizhu Wu

  DOI：10.1016/s1872-2067(18)63095-5

  日期：2018.7

  hydrogen-evolution dimerization of styrenes via the synergistic merger of Acr+-Mes photocatalyst and cobaloxime proton reduction catalysts. By utilizing this dual catalyst system, 1,2-dihydro-1-arylnaphthalene derivatives can be directly constructed from commercially available styrenes. Our reaction proceeds smoothly under mild conditions without the need for oxidants or hydrogen atom transfer reagents, and

  摘要 我们报道了通过 Acr+-Mes 光催化剂和钴肟质子还原催化剂的协同合并实现苯乙烯的析氢二聚反应。通过利用这种双催化剂体系，1,2-二氢-1-芳基萘衍生物可以直接由市售苯乙烯构成。我们的反应在温和的条件下顺利进行，不需要氧化剂或氢原子转移试剂，唯一的副产物是氢气。机理研究表明，该反应是由可见光照射下的光致电子转移引发的。
• Novel Cerium(IV) ammonium nitrate induced dimerization of methoxystyrenes
  作者：Vijay Nair、Jessy Mathew、Puthuparampil P. Kanakamma、Sreeletha B. Panicker、V. Sheeba、S. Zeena、Guenter K. Eigendorf

  DOI：10.1016/s0040-4039(97)00279-7

  日期：1997.3

  Methoxystyrenes undergo facile dimerization when heated with Cerium (IV) ammonium nitrate in methanol; cyclized products are obtained in acetonitrile. (C) 1997 Elsevier Science Ltd.
• Nanosecond and Picosecond Dynamics of the Radical Cation Mediated Dimerization of 4-Methoxystyrene
  作者：N. P. Schepp、L. J. Johnston

  DOI：10.1021/ja00094a049

  日期：1994.7

  The addition of the 4-methoxystyrene radical cation to neutral 4-methoxystyrene and the cleavage reactions of the 1,2-bis(4-methoxyphenyl)cyclobutane radical cation in acetonitrile have been studied by product analysis and by nanosecond and picosecond transient absorption spectroscopy. The main product upon radical cation mediated dimerization of 4-methoxystyrene using chloranil as the electron transfer sensitizer is a substituted dihydronaphthalene, 1,2-dihydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene, at low concentrations of 4-methoxystyrene. At higher concentrations, the main product is 1,2-bis(4-methoxyphenyl)cyclobutane. Cleavage of the cyclobutane radical cation is found to give 4-methoxystyrene and the dihydronaphthalene in a 1:3 ratio. In the time-resolved experiments, the radical cations are generated from 4-methoxystyrene and 1,2-bis(4-methoxyphenyl)cyclobutane by 266-nm photoionization or by 355-nm photoinduced electron transfer using triplet chloranil as the sensitizer. A transient with an absorption maximum at 500 nm is observed as a short-lived intermediate in both the radical cation mediated 4-methoxystyrene dimerization and the cyclobutane radical cation cleavage experiments. Spectroscopic and kinetic considerations lead to the conclusion that this transient is a substituted hexatriene radical cation produced as an intermediate in the conversion of the 1,2-bis(4-methoxyphenyl)cyclobutane radical cation to the dihydronaphthalene. Observed rate constants for the decay of the 4-methoxystyrene radical cation measured at 4-methoxystyrene concentrations of 0.0001 to 0.015 M increase in a linear fashion with concentration, while at concentrations >0.2 M, the observed rate constant is found to be independent of concentration. Analysis of the kinetic data according to a rate law derived from a concerted [2 + 1] mechanism leads to the following rate constants: k(1) = 1.4 X 10(9) M(-1) s(-1) for the addition reaction, k(-1) = 8 x 10(7) s(-1) for the cycloreversion reaction, k(2) = 2.5 X 10(8) s(-1) for the rearrangement of the cyclobutane radical cation, and k(3) = 1.5 X 10(10) M(-1) s(-1) for the reduction of the cyclobutane radical cation by neutral 4-methoxystyrene. Monitoring the kinetics of the reactions of the cyclobutane radical cation gives the same values for the rate constants k(2) and k(-1).