1-(3,4-dimethoxyphenyl)-3,4-dihydronaphthalene | 78238-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3,4-dimethoxyphenyl)-3,4-dihydronaphthalene
• 英文别名: 4-(3,4-Dimethoxyphenyl)-1,2-dihydronaphthalene
• CAS: 78238-95-6
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: GMTMFAHFAXACFI-UHFFFAOYSA-N

物化性质

• 沸点：
  175-180 °C(Press: 2.5 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-3,4-dihydronaphthalene 在 Adam’s catalyst 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以86%的产率得到1-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Bandaranayake, Wickramasinghe M.; Riggs, Noel V., Australian Journal of Chemistry, 1981, vol. 34, # 1, p. 115 - 129

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴黎芦醚 、 3,4-二氢-1(2H)-萘酮 在 正丁基锂 作用下， 生成 1-(3,4-dimethoxyphenyl)-3,4-dihydronaphthalene
  参考文献：
  名称：

  Bandaranayake, Wickramasinghe M.; Riggs, Noel V., Australian Journal of Chemistry, 1981, vol. 34, # 1, p. 115 - 129

  摘要：

  DOI：

文献信息

• An Improved Method for the Preparation of Cyclic Conjugated Nitroolefins
  作者：Debasis Ghosh、David E. Nichols

  DOI：10.1055/s-1996-4202

  日期：1996.2

  Nitration of cyclic conjugated olefins was achieved in a one-pot procedure using nitryl iodide generated in situ from iodine and potassium nitrite complexed with 18-crown-6 in tetrahydrofuran under sonication/stirring, followed by treatment of the unstable iodo nitro compound with base. The yield of the nitro compound varied from 52 to 90%.

  使用碘和亚硝酸钾在四氢呋喃中与 18-crown-6 络合在超声处理/搅拌下原位生成的硝酰碘，以一锅法实现环状共轭烯烃的硝化，然后用碱处理不稳定的碘硝基化合物。硝基化合物的产率从52%到90%不等。
• Regioselective Annulation of Alicyclic−Aromatic Dienes with 3-Halo-3-cyclobutene-1,2-diones. Synthesis of Annulated α-Halobenzocyclobutenones¹
  作者：Arthur H. Schmidt、Gunnar Kircher、Elmar Bräu

  DOI：10.1021/jo971948n

  日期：1998.3.1

  4-(1-Cycloalken-1-yl)-1,2-dialkoxybenzenes 8, 10, and 11 and 5-(1-cycloalken-1-yl)-1,3-benzodioxoles 12-15 react with the semisquaric halides 5a and 5b in a dehydrative annulation process to give the annulated alpha-halobenzocyclobutenones 9a,b and 16a,b-21a,b in poor to good yields (20-76%). The reaction failed with alicyclic-aromatic dienes having no or only one alkoxy group in the benzene ring. The dehydrative annulation process could be extended to 4-(3,4-dimethoxyphenyl)-1,2-dihydronaphthalene (24), affording the highly annulated alpha-chlorobenzocyclobutenone 25 in 50% yield. In the case of 5-(1-cyclobuten-1-yl)-1,3-benzodioxole (22), reaction with the semisquaric halides 5a,b yielded the dicyclobutanaphthodioxole-1,2-dione (23) as the sole product in a dehydrochlorinative annulation process. A reaction pathway has been suggested for the dehydrative annulation process. Several of the annulated alpha-halobenzocyclobutenones prepared were submitted to selected chemical transformations. Thus, the reaction with tributyltin hydride afforded the annulated benzocyclobutenones 26a-f in excellent yields (74-78%), and treatment with silver trifluoroacetate afforded the alpha-(trifluoroacetoxy)benzocyclobutenones 27a-c in 71-79% yields.
• BANDARANAYAKE W. M.; RIGGS N. V., AUSTRAL. J. CHEM., 1981, 34, NO 1, 115-129
  作者：BANDARANAYAKE W. M.、 RIGGS N. V.

  DOI：——

  日期：——
• Bandaranayake, Wickramasinghe M.; Riggs, Noel V., Australian Journal of Chemistry, 1981, vol. 34, # 1, p. 115 - 129
  作者：Bandaranayake, Wickramasinghe M.、Riggs, Noel V.

  DOI：——

  日期：——
• Assessment of dopamine D1 receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393
  作者：Alia H. Clark、John D. McCorvy、Val J. Watts、David E. Nichols

  DOI：10.1016/j.bmc.2011.07.057

  日期：2011.9

  To assess the effect of conformational mobility on receptor activity, the beta-phenyl substituent of dopamine D-1 agonist ligands of the phenylbenzazepine class, (+/-)-6,6a, 7,8,9,13b-hexahydro-5H-benzo[d] naphtho[ 2,1-b] azepine-11,12-diol (8), and its oxygen and sulfur bioisosteres 9 and 10, respectively, were synthesized as conformationally-restricted analogs of SKF38393, a dopamine D-1-selective partial agonist. Compounds trans-8b, 9, and 10 showed binding affinity comparable to that of SKF38393, but functionally, they displayed only very weak agonist activity. These results suggest that the conformationally-restricted structure of the analogs cannot adopt a binding orientation that is necessary for agonist activity. (C) 2011 Elsevier Ltd. All rights reserved.