2-methyl-5,6,7,8-tetrahydro-naphthalen-1-ol | 41059-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-methyl-5,6,7,8-tetrahydro-naphthalen-1-ol
• 英文别名: 2-methyl-5,6,7,8-tetrahydronaphthalen-1-ol；2-methyl-5,6,7,8-tetrahydro-1-naphthol；1-Hydroxy-2-methyl-5.6.7.8-tetrahydro-naphthalin；2-Methyl-5,6,7,8-tetrahydro-[1]naphthol；5-Hydroxy-6-methyl-tetralin；1-Hydroxy-2-methyl-5,6,7,8-tetrahydro-naphthalin
• CAS: 41059-12-5
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: WBMBHELKPVWKDY-UHFFFAOYSA-N

物化性质

• 沸点：
  276.6±29.0 °C(Predicted)
• 密度：
  1.074±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：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 sodium nitrite 作用下， 生成 2-methyl-5,6,7,8-tetrahydro-naphthalen-1-ol
  参考文献：
  名称：

  Vesely; Kapp, Chemicke Listy, 1930, vol. 24, p. 97,99

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Aromatization of Enediynes via Highly Regioselective Nucleophilic Additions on a π-Alkyne Functionality. A Useful Method for the Synthesis of Functionalized Benzene Derivatives
  作者：Arjan Odedra、Chang-Jung Wu、Taduri Bhanu Pratap、Chun-Wei Huang、Ying-Fen Ran、Rai-Shung Liu

  DOI：10.1021/ja043047j

  日期：2005.3.1

  TpRu(PPh3)(CH3CN)2 PF6 (10 mol %) catalyst effected the nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles, and dimethyl malonate to unfunctionalized enediynes under suitable conditions (100 degrees C, 12-24 h) and gave functionalized benzene products in good yields. In this novel cyclization, nucleophiles very regioselectively attack the internal C1' alkyne carbon of enediynes

  TpRu(PPh3)(CH3CN)2 PF6 (10 mol %) 催化剂在合适的条件下（100 摄氏度，12-24 小时）实现了水、醇、苯胺、乙酰丙酮、吡咯和丙二酸二甲酯与未官能化的烯二炔的亲核加成和以良好的收率得到官能化苯产物。在这种新颖的环化中，亲核试剂非常区域选择性地攻击烯二炔的内部 C1' 炔烃碳，得到苯衍生物作为单一区域异构体。使用甲氧基取代基的实验排除了萘基阳离子作为反应中间体参与（邻乙炔基苯基）炔烃环化的可能。氘标记实验表明催化活性物质是钌-π-炔烃而不是钌-亚乙烯基物质。o-(2' -碘乙炔基）苯基炔烃与醇。我们在一系列实验的基础上提出了这种亲核芳构化的亲核加成/插入机制。
• Ruthenium-Catalyzed Rearrangement of <i>cis</i>-1-Ethynyl-2-vinyloxiranes to Substituted Phenols
  作者：Rai-Shung Liu、Shambabu Maddirala、Arjan Odedra、Bhanu Taduri

  DOI：10.1055/s-2006-926255

  日期：——

  Catalytic cyclization of cis-1-ethynyl-2-vinyloxiranes was implemented with TpRuPPh3(CH3CN)2PF6 catalyst (10 mol%), to give 2,6-disubstituted phenols in reasonable yields. Under similar conditions, 1,1,2,2-tetrasubstituted oxirane gave the 2,3,6-trisubstituted phenol with skeleton reorganization. On the basis of 2H- and 13C-labeling results, we propose that the reaction mechanism involves electrocyclization of ruthenium-vinylidene intermediate with cleavage of the carbon-oxygen bond of the epoxide.

  使用TpRuPPh3(CH3CN)2PF6催化剂（10 mol%）实施了顺式-1-乙炔基-2-乙烯氧杂环丁烷的催化环化反应，合理产率地得到了2,6-二取代苯酚。在类似的条件下，1,1,2,2-四取代氧杂环丁烷通过骨架重排生成了2,3,6-三取代苯酚。基于2H和13C标记结果，我们提出反应机制涉及钌-乙烯叉中间体的电子环化以及环氧化物碳氧键的断裂。
• Selective Hydrogenation of Naphthols to Tetralones over Supported Palladium Catalysts in Supercritical Carbon Dioxide Solvent
  作者：Eiichi Mine、Norihito Hiyoshi、Osamu Sato、Chandrashekhar V. Rode、Masayuki Shirai

  DOI：10.1246/cl.2006.780

  日期：2006.7

  Naphthols were selectively hydrogenated to the corresponding tetralones over supported palladium metal catalysts in supercritical carbon dioxide solvent.

  在超临界二氧化碳溶剂中，通过负载型钯金属催化剂，选择性地将萘酚氢化成相应的四氢萘酮。
• Synthesis of Mono- and Polycyclic Tricarbonyliron Cyclohexa-2,4-dienone Complexes and Phenols from Tosylhydrazones of Acyclic Dienone Complexes
  作者：Michel Franck-Neumann、Philippe Geoffroy、Dominique Gassmann

  DOI：10.1055/s-2002-35598

  日期：——

  Cyclohexa-2,4-dienones stabilized by coordination to tricarbonyliron are obtained when the tosylhydrazones of tricarbon­yliron-complexed α-dienones are thermolyzed in the presence of strong bases. This cyclocarbonylation reaction of carbenic intermediates is fairly general and can be used to synthesize various mono and polycyclic cyclohexadienone complexes or their decomplexed phenolic tautomers, and among them a new salicylate in the phenanthrene series.

  通过在强碱存在下热解三羰基铁复合的α-二烯酮的托烯肼酮，可以得到与三羰基铁配位稳定的环己烯-2,4-二酮。这种从羰基中间体的环羰基化反应相当普遍，可以用来合成各种单环和多环环己烯二酮复合物或其去复合的酚类互变异构体，其中包括一种新的在菲系列中的水杨酸盐。
• Efficient synthetic routes to aromatic compounds using ring-closing olefin metathesis followed by dehydration, oxidation, and tautomerization
  作者：Kazuhiro Yoshida、Takeharu Toyoshima、Tsuneo Imamoto

  DOI：10.1039/b705581a

  日期：——

  A simple synthetic approach to aromatic compounds using combinations of RCM, dehydration, oxidation, and tautomerization is described.

  描述了一种通过组合环加成反应（RCM）、脱水、氧化和互变异构化的简单合成方法来制备芳香化合物。