1,2-dihydro-6-methoxy-4,7-dimethylnaphthalene | 107203-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-dihydro-6-methoxy-4,7-dimethylnaphthalene
• 英文别名: 6-methoxy-4,7-dimethyl-1,2-dihydronaphthalene
• CAS: 107203-36-1
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: MAHJMIXSRGCOOP-UHFFFAOYSA-N

物化性质

• 沸点：
  140-145 °C(Press: 6 Torr)
• 密度：
  1.002±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-6-methoxy-4,7-dimethylnaphthalene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到(±)-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of (±)heritol

  摘要：

  Synthesis of (+/-)heritol and epi-heritol is described. The key step is the osmylation of the unsaturated ester 9a. Osmylation is used as a tool to construct the alpha,beta-unsaturated delta-lactone system.

  DOI：

  10.1016/s0040-4020(01)86527-3
• 作为产物：
  描述：

  2-甲基苯甲醚 在 盐酸 、 三氯化铝 、 硫酸 、 三氟乙酸 、 三氟乙酸酐 、 锌 作用下， 以 硝基苯 为溶剂， 反应 31.17h， 生成 1,2-dihydro-6-methoxy-4,7-dimethylnaphthalene
  参考文献：
  名称：

  Synthesis of (±)heritol

  摘要：

  Synthesis of (+/-)heritol and epi-heritol is described. The key step is the osmylation of the unsaturated ester 9a. Osmylation is used as a tool to construct the alpha,beta-unsaturated delta-lactone system.

  DOI：

  10.1016/s0040-4020(01)86527-3

文献信息

• Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
  作者：Yu Zhang、Yuting Liao、Xiaohua Liu、Xi Xu、Lili Lin、Xiaoming Feng

  DOI：10.1039/c7sc02809a

  日期：——

  ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95:5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.

  使用N，N'-二氧化物-（（III）络合物催化剂完成了用氧氮丙啶对萘的对映体选择性羟基化脱芳香化反应。各种取代的邻-quinols可以以高产率（高达99％）和对映选择性（高达95来获得：5 ER）。该方法可用于克级反应中的生物活性lacileilenes的合成。基于实验研究和先前的工作，提出了一种可能的催化模型。
• Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
  作者：Fernanda A Siqueira、Eloisa E Ishikawa、André Fogaça、Andréa T Faccio、Vânia M. T Carneiro、Rafael R. S Soares、Aline Utaka、Iris R. M Tébéka、Marcin Bielawski、Berit Olofsson、Luiz F Silva Jr

  DOI：10.1590/s0103-50532011000900024

  日期：——

  A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH) OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1: 4 mixture of TFE: CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.
• Transition-Metal-Catalyzed Oxidations. 11.¹ Total Synthesis of (±)-Lacinilene C Methyl Ether by β-Naphthol to α-Ketol Oxidation
  作者：Karsten Krohn、Gregor Zimmermann

  DOI：10.1021/jo9801566

  日期：1998.6.1
• (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
  作者：Graziela G. Bianco、Helena M. C. Ferraz、Arinice M. Costa、Letícia V. Costa-Lotufo、Cláudia Pessoa、Manoel O. de Moraes、Marcus G. Schrems、Andreas Pfaltz、Luiz F. Silva

  DOI：10.1021/jo9000405

  日期：2009.3.20

  The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.
• Identification and synthesis of Trinorcadalene Phytoalexins formed by Hibiscus cannabinus in honour of Professor G. H. Neil Towers 75th birthday
  作者：Alois A. Bell、Robert D. Stipanovic、Jiuxu Zhang、Marshall E. Mace、Joseph H. Reibenspies

  DOI：10.1016/s0031-9422(98)00183-6

  日期：1998.9

  Two trinorcadalene phytoalexins, hibiscanal (2,8-dihydroxy-4,7-dimethoxy-6-methyl-1-naphthaldehyde) and o-hibiscanone (3,8-dimethyl-1,2-naphthoquinone), were isolated and identified from stem stele of kenaf (Hibiscus cannabinus) inoculated with the fungal pathogen Verticillium dahliae. o-Hibiscanone also was synthesized. The ED50 values of hibiscanal and o-hibiscanone against V. dahliae were 25.83 and 1.18 mu g/ml, respectively. o-Hibiscanone killed all propagules of V. dahliae and Fusarium oxysporum rtm f. sp. vasinfectum at 8 mu g/ml and 12 mu g/ml, respectively. o-Hibiscanone is more toxic to V. dahliae than desoxyhemigossypol, the most toxic phytoalexin known in cotton (Gossypium species), or mansonone C (3,8-dimethyl-5-isopropyl-1,2-naphthoquinone) which has been isolated from other malvaceous species. The implications of these findings for the genetic engineering of cotton phytoalexins is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.