1,4-二甲基-1,2-二氢萘 | 5195-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4-二甲基-1,2-二氢萘
• 英文名称: 1,4-dimethyl-1,2-dihydronaphthalene
• 英文别名: 1,4-dimethyl-1,2-dihydro-naphthalene；1,4-Dimethyl-1,2-dihydro-naphthalin；1,4-Dimethyl-Δ¹-dihydronaphthalin；1,4-Dimethyl-3,4-dihydro-naphthalin；1,2-Dihydro-1,4-dimethylnaphthalin；1,4-Dimethyl-1,2-dihydro-nphthalin
• CAS: 5195-36-8
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: NQMBDRGLTZNMLX-UHFFFAOYSA-N

物化性质

• 沸点：
  87-88 °C
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：

  1,4-二甲基-1,2-二氢萘 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 1,4-二甲基-1,2,3,4-四氢萘
  参考文献：
  名称：

  Gelin,R.; Chantegrel,B., Bulletin de la Societe Chimique de France, 1971, p. 2527 - 2544

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 、 溶剂黄146 作用下， 生成 1,4-二甲基-1,2-二氢萘
  参考文献：
  名称：

  Colonge; Collomb, Bulletin de la Societe Chimique de France, 1951, p. 285,286

  摘要：

  DOI：

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。
• Carbon-13 magnetic resonance of hydroaromatics. II. Conformation of Tetralin and tetrahydroanthracene and their methyl derivatives
  作者：Frederick G. Morin、W. James Horton、David M. Grant、Don K. Dalling、Ronald J. Pugmire

  DOI：10.1021/ja00350a042

  日期：1983.6

  Carbon-13 chemical shift data have been acquired for 36 methylated tetralins and tetrahydroanthracenes. A least-squares regression analysis has been undertaken on the ring carbons of compounds of unequivocal conformation to determine methyl substituent parameters for the two distinct aliphatic positions and the results have been used to estimate the position of equilibrium of conformationally mobile

  已获得 36 种甲基化四氢萘和四氢蒽的碳 13 化学位移数据。对明确构象的化合物的环碳进行了最小二乘回归分析，以确定两个不同脂肪族位置的甲基取代参数，结果已用于估计构象移动化合物的平衡位置。得出的结论是，1-甲基萘满在室温下以基本相同的构象异构体存在，但 2-甲基衍生物主要由具有赤道甲基的构象支配。将取代基参数与先前为甲基化环己烷确定的参数进行比较。对甲基化学位移的类似分析没有成功，部分原因是饱和环的高度柔性。
• Ring Contraction of 1,2-Dihydronaphthalenes Promoted by Thallium(III) in Acetonitrile: A Diastereoselective Approach to Indanes
  作者：Luiz Silva、Helena Ferraz、Vânia Carneiro

  DOI：10.1055/s-0028-1083308

  日期：——

  indanes are conveniently accessed by a stereoselective ring contraction of 1,2-dihydronaphthalenes upon treatment with thallium(III) nitrate (TTN) in acetonitrile. Under­ these conditions, the oxidative rearrangement of either di- or trisubstituted double bonds is possible. thallium(III) nitrate - carbocycles - indanes - ring contractions - oxidative rearrangements

  通过在乙腈中用硝酸al（III）（TTN）处理1,2-二氢萘的立体选择性环收缩，可方便地获得反式-1,3-二取代的茚满。在这些条件下，二或三取代的双键的氧化重排是可能的。 硝酸-碳环-茚满-环收缩-氧化重排
• 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.
• Quillet,J.-P.; Dreux,J., Bulletin de la Societe Chimique de France, 1966, p. 645 - 652
  作者：Quillet,J.-P.、Dreux,J.

  DOI：——

  日期：——