6,8-dimethyl-1,2-dihydronaphthalene | 53156-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,8-dimethyl-1,2-dihydronaphthalene
• 英文别名: 6,8-Dimethyl-1,2-dihydronaphtalin
• CAS: 53156-01-7
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: ZRSRIWPFNZUPHS-UHFFFAOYSA-N

物化性质

• 沸点：
  243.1±35.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6,8-dimethyl-1,2-dihydronaphthalene 在 硫酸 、 双氧水 、 sodium ethanolate 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 3-amino-5,6-dihydro-7,9-dimethylbenzo[f]quinazolin-1(2H)-one
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004
• 作为产物：
  描述：

  (+/-)-5,7-Dimethyl-1-tetralol 在 acid 作用下， 生成 6,8-dimethyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  光学活性锰(III)配合物催化未官能化烯烃与分子氧和醛的对映选择性环氧化

  摘要：

  结合使用分子氧、氧化剂和新戊醛（一种还原剂）对未官能化烯烃的对映选择性环氧化反应在催化量的...

  DOI：

  10.1246/cl.1992.2231

文献信息

• Iodine(III)-Promoted Ring Contraction of 1,2-Dihydronaphthalenes:  A Diastereoselective Total Synthesis of (±)-Indatraline
  作者：Luiz F. Silva,、Fernanda A. Siqueira、Eliane C. Pedrozo、Fabiana Y. M. Vieira、Antônio C. Doriguetto

  DOI：10.1021/ol070027o

  日期：2007.4.1

  [reaction: see text] A new approach for the synthesis of (+/-)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated

  [反应：见正文]描述了一种合成（+/-）-茚达林的新方法，它是一种具有多种生物活性的3-苯基-1-茚满胺。该策略的关键步骤是由PhI（OTs）OH促进的1,2-二氢萘的非对映选择性环收缩，以构建茚满环体系。还研究了其他1,2-二氢萘的氧化重排，将这种方法推广到茚满。
• Aromatische [1,5s]-sigmatropische H-Verschiebungen in Arylallenen
  作者：Heinz Heimgartner、Janos Zsindely、Hans-J�rgen Hansen、Hans Schmid

  DOI：10.1002/hlca.19730560833

  日期：1973.12.12

  1-Mesityl allene (1), 1-mesityl-3-methyl allene (2) and 1-mesityl-3,3-dimethyl allene (3) rearrange thermally at 150–190° in decane via [1,5s]sigmatropic H-shifts to yield the o-quinodimethanes 4, which cyclise to give the 1,2-dihydronaphthalenes 5 and 6 and/or undergo [1,7 a]sigmatropic H-shifts to give 1-mesityl-(Z)-buta-1, 3-dienes (Z)-7 and (Z)-8, respectively (Schemes 1,3,4 and 5) in almost quantitative

  1-三甲苯基异戊烯（1），1-三甲苯基-3-甲基丙二烯（2）和1-三甲苯基-3,3-二甲基丙二烯（3）在癸烷中通过[1.5 s ]σ-H-在150-190°下热重排移位得到邻喹啉甲烷4，其环化生成1,2-二氢萘5和6和/或经历[1,7 a ]σH移位得到1-甲磺酰基-（Z）-buta-1， 3-二烯（Z）-7和（Z）-8（方案1,3,4和5）的数量几乎是定量的。这些异构化的活化参数在表1中给出。1-Mesityl-1-甲基丙二烯（9）在190°下异构化，以4,50 ％的收率得到4,5,7-三甲基-1,2-二氢萘（17）。方案6）。
• Enantioselective Epoxidation of Unfunctionalized Olefins with Molecular Oxygen and Aldehyde Catalyzed by Optically Active Manganese(III) Complexes
  作者：Tohru Yamada、Kiyomi Imagawa、Takushi Nagata、Teruaki Mukaiyama

  DOI：10.1246/cl.1992.2231

  日期：1992.11

  Enantioselective epoxidation of unfunctionalized olefins with combined use of molecular oxygen, an oxidant, and pivalaldehyde, a reductant, was demonstrated in the presence of a catalytic amount of...

  结合使用分子氧、氧化剂和新戊醛（一种还原剂）对未官能化烯烃的对映选择性环氧化反应在催化量的...
• 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.
• Palladium-Catalyzed Cyclization of 1,ω-Dienols:  Multiple Ways to Intramolecularly Trap a Carbocation
  作者：Vasily N. Korotchenko、Michel R. Gagné

  DOI：10.1021/jo0705871

  日期：2007.6.1

  The tandem catalytic cyclization-rearrangement of 1,omega-dien-3-ols by palladium(II) produces different types of products, depending on the structure of starting material. The pinacol rearrangement, benzannulation, and oxy-Cope rearrangement are major pathways of transforming the putative sigma-alkylpalladium carbocation. Turnover of the cyclization is achieved by beta-hydride elimination and reoxidation of palladium with benzoquinone. The overall course of the reaction is very sensitive to small changes in the substrate structure.