1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene | 87797-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene
• 英文别名: 1-(4-methoxyphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene；1-(p-methoxyphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene；7-methoxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene；1-(4-methoxyphenyl)-7-methoxytetralin；7-methoxy-1-(4-methoxy-phenyl)-1,2,3,4-tetrahydro-naphthalene；7-Methoxy-1-(4-methoxy-phenyl)-1,2,3,4-tetrahydro-naphthalin
• CAS: 87797-13-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: WBJZURYAMJCADG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene 在 sulfur 作用下， 生成 7-甲氧基-1-(4-甲氧基苯基)萘
  参考文献：
  名称：

  Dimeric Propenyl Phenol Ethers. XIII. on Metanethole and its Teralin Isomers

  摘要：

  DOI：

  10.1021/jo50001a001
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 17.25h， 生成 1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene
  参考文献：
  名称：

  仿生合成芳基四氢木脂素的方法

  摘要：

  3-芳基丙基取代的醌-甲基缩酮的BF 3催化环化为芳基四氢化萘提供了温和的仿生途径。报告了产物的1 H-和13 C-NMR谱。

  DOI：

  10.1016/s0040-4020(01)96619-0

文献信息

• Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes
  作者：M. Carreño、Antonio Urbano、Marcos González-López、Alfonso Latorre

  DOI：10.1055/s-2005-869857

  日期：——

  Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes occurred preferentially at the A-ring when no substituents were present at the ortho-positions of the aryl group (up to 100% selectivity), to afford 1-aryl-7-methoxy-1,2,3,4-tetrahydronaphthalenes. Ortho-substitution of the 1-aryl moiety favored B-ring reduction (up to 85:15 selectivity) giving rise, after acidic hydrolysis of the ­vinyl ether intermediate, to the corresponding 8-aryl-2-tetralones.

  当1-芳基-7-甲氧基萘的苯基上没有在邻位存在取代基时，Na/EtOH还原反应优先发生在A环（选择性高达100%），生成1-芳基-7-甲氧基-1,2,3,4-四氢萘。而当1-芳基部分的邻位存在取代基时，则偏向于对B环的还原（选择性高达85:15），经乙烯基醚中间体的酸催化水解后，生成相应的8-芳基-2-四氢萘酮。
• Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives
  作者：Leifeng Wang、Fengjin Wu、Jiean Chen、David A. Nicewicz、Yong Huang

  DOI：10.1002/anie.201702940

  日期：2017.6.6

  We report a formal [4+2] cycloaddition reaction of styrenes under visible‐light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo‐ and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic

  我们报告了可见光催化下苯乙烯的正式[4 + 2]环加成反应。发现具有不同电子或空间特性的两个苯乙烯分子可以以良好的收率，优异的化学和区域选择性相互反应。该反应提供了从容易获得的苯乙烯直接进入多取代的四氢萘骨架的途径。复杂的三环和四环四氢化萘类似物可从环状底物中以高收率和高达20/1的非对映选择性制备。
• Visible-Light [4+2] Homodimerization of Decomposition-Prone Styrenes via Electron Transfer Catalysis of Diaryl Diselenides
  作者：Inho Jang、Hun Young Kim、Kyungsoo Oh

  DOI：10.1021/acs.orglett.4c01210

  日期：——

  The facile electron transfer catalysis of diaryl diselenides was utilized for the visible-light [4+2] homodimerization of decomposition-prone styrenes. The reaction required only 0.5 mol % TPT+BF4– photocatalyst and 1.5 mol % electron transfer catalyst (ArSe)2. The spontaneous electron transfer capability of diaryl diselenides was demonstrated for the first time, leading to the sequestration of redox-prone

  二芳基二硒化物的简易电子转移催化被用于易分解苯乙烯的可见光[4+2]均二聚。该反应仅需要0.5 mol% TPT + BF 4 –光催化剂和1.5 mol% 电子转移催化剂(ArSe) 2 。首次证明了二芳基二硒化物的自发电子转移能力，导致通过电子转移过程螯合氧化还原倾向的自由基阳离子中间体。多种易于聚合的苯乙烯顺利地进行可见光促进的[4+2]均二聚反应，生成四氢化萘衍生物。
• General Synthesis of 8-Aryl-2-tetralones
  作者：M. Carmen Carreño、Marcos González-López、Alfonso Latorre、Antonio Urbano

  DOI：10.1021/jo060688j

  日期：2006.6.1

  Two alternative routes are described for the synthesis of 8-aryl-2-tetralones (1). Route A starts from alpha-tetralone 3 and involves 3 or 4 steps, with the selective Na-EtOH reduction of 1-aryl-7-methoxynaphthalenes 2 being the key step. The exclusive reduction of the A ring of naphthalenes 2 occurs when the aryl group at C-1 has no substituent at the ortho positions, affording tetrahydronaphthalenes 11. Reduction of the B ring of 2 becomes the major process when the aryl fragment has two substituents at the ortho positions, affording 8-aryl-2-tetralones 1 as the major component. Route B involves 5 steps starting from 2-tetralone 5, with the key step being the Suzuki coupling with triflate 4. This approach allows the synthesis of 8-aryl-2-tetralones 1 with no substituent at the ortho positions of the aryl fragment and with naphthalene and anthracene rings at C-8.
• 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).