1-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthol | 149385-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthol
• 英文别名: 1-(Hydroxymethyl)-5,6,7,8-tetrahydronaphthalen-2-ol
• CAS: 149385-34-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: SCQQCQJHKSLBEB-UHFFFAOYSA-N

物化性质

• 熔点：
  52-56 °C
• 沸点：
  355.8±42.0 °C(predicted)
• 密度：
  1.200±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthol 在 sodium periodate 、 叔丁基二甲基氯硅烷 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.0h， 生成 6-羟基-1,2,3,4-四氢-5-萘甲醛
  参考文献：
  名称：

  Synthesis of Fused Aromatic [1,3]Dioxoles from 2-Hydroxymethylphenols

  摘要：

  在非极性溶剂（甲苯、四氯化碳）中，添加TBDMSCl的条件下，螺环氧化环己二烯酮的重排反应最好进行，从而形成苯并[1,3]二恶烷。此外，还描述了将其应用于萘和四氢萘衍生物的合成过程。

  DOI：

  10.1055/s-1997-1037
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 、 聚合甲醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 120.0h， 以20%的产率得到1-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthol
  参考文献：
  名称：

  Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies

  摘要：

  Six dissymmetric calix[4]arenes with C4 symmetry consisting of four 3,4-disubstituted phenolic units have been obtained by condensation of the respective 2- or 6-hydroxymethylated phenols. The regular incorporation of the phenolic units into the macrocycle was established on the basis of H-1 NMR spectra and in one case also by X-ray analysis. One example for a calixarene with C2-symmetry consisting of p-cresol and 3,4-dimethylphenol units in alternating sequence was also prepared. Calixarene 4a consisting of 3,4-dimethylphenol units shows a lower energy barrier (DELTAG(double dagger) = 13.4 kcal/mol) for the cone-to-cone inversion in CDCl3 than p-methylcalix[4]arene (DELTAG(double dagger) = 14.6 kcal/mol). The dissymmetric calixarenes 4 could be conformationally fixed by alkylation of the phenolic hydroxyl group. Due to the equivalence of all four phenolic units, mono- and 1,3-di-derivatives could be obtained in addition to tetra derivatives. A tetraester derivative in the cone conformation, like the parent calix[4]arene, crystallizes as a racemate. In solution these tetraester derivatives exist in a distorted cone conformation with C2 symmetry. Dynamic H-1 NMR spectra reveal an energy barrier of DELTAG(double dagger) = 13.3-13.4 kcal/mol for the C2-to-C2 interconversion with the C4-cone as transition state.

  DOI：

  10.1021/jo00067a040

文献信息

• Molecular Complexity from Aromatics:  A Novel, Stereoselective Route to Tricyclo[5.2.2.0^1,5]undecenones, Tricyclo[6.2.2.0^1,6]Dodecenones, and [<i>n</i>.3.3]Propellanes
  作者：Vishwakarma Singh、Pramod K. Sahu、Raj Bahadur Singh、Shaikh M. Mobin

  DOI：10.1021/jo702168s

  日期：2007.12.1

  stereoselective route to functionalized and substituted tricyclo [5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized

  据报道，从简单的芳香族前体到官能化和取代的三环[5.2.2.0 1,5 ]十一碳烯，三环[6.2.2.0 1,6 ]十二碳烯以及[3.3.3]-和[4.3.3]丙炔的一般立体选择路线。该方法涉及用各种丙烯酸酯生成和环化环己二环2,4-二烯酮，然后处理所得的三环加合物，从而导致官能化的三环[5.2.2.0 1,5 ]十一碳烯和三环[6.2.2.0 1,6 ]十二碳烯具有β，γ-烯酮发色团。三环发色体系的光化学反应，然后进行还原性裂解，有效地进入了螺旋桨。
• 2-Aminomethyl-6-sulfamoylphenolderivate, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0088345A2

  公开（公告）日：1983-09-14

  Die Erfindung betrifft 2-Aminomethylphenole der Formel I in welcher R1 und R2 für Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl oder Benzyl, das gegebenenfalls durch Alkyl, Alkoxy oder Halogen substituiert ist, steht, R3 und R5 Wasserstoff, Halogen, Alkyl oder Alkoxy, R4 Halogen, Alkyl oder Cycloalkyl bedeuten und R6 und R7 für Wasserstoff oder Alkyl stehen, wobei die Reste R1 und R2, R" und R7 und/oder zwei der Reste R3, R4 und R5 eine Alkylenkette bilden können, die gegebenenfalls durch Methylgruppen substituiert und die im Falle der Reste R1, R2, R6 und R7 auch durch Sauerstoffatome, Schwefelatome und/oder Iminogruppen unterbrochen sein kann, sowie deren physiologisch verträglichen Salze, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen.

  本发明涉及式 I 的 2-氨基甲基苯酚。 其中，R1 和 R2 是氢、烷基、烯基、炔基、环烷基或任选被烷基、烷氧基或卤素取代的苄基，R3 和 R5 是氢、卤素、烷基或烷氧基，R4 是卤素、烷基或环烷基，R6 和 R7 是氢或烷基、R4和R5可形成一条烯链，该烯链可任选被甲基取代，在自由基R1、R2、R6和R7的情况下，该烯链也可被氧原子、硫原子和/或亚胺基打断。
• Cycloaddition of annulated cyclohexa-2,4-dienones and novel reduction of halogen at bridgehead: an expedient route to tetracyclo[6.5.2.02,7.09,13]pentadec-2(7),11-dien-14-one and framework of conidiogenol and conidiogenone
  作者：Vishwakarma Singh、Raj Bahadur Singh、Shaikh M. Mobin

  DOI：10.1016/j.tet.2009.07.051

  日期：2009.9

  An expedient route to tetracyclo[6.5.2.0(2,7).0(9,13)]pentadec-2(7),11-dien-14-one and tetracyclic framework of conidiogenol have been reported. Cycloaddition of annulated cyclohexa-2,4-dienone with cyclopentadiene, photochemical oxa-di-pi-methane reaction and a highly unusual dehalogenation of bridgehead halogen are the key features of our methodology. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Fused Aromatic [1,3]Dioxoles from 2-Hydroxymethylphenols
  作者：Jean-Pierre Gesson、Martine Mondon、Natacha Pokrovska

  DOI：10.1055/s-1997-1037

  日期：——

  The rearrangement of spiroepoxycyclohexadienones to benzo[1,3]dioxoles is best carried out in a non polar solvent (toluene, CCl4) in presence of TBDMSCl. Application to the synthesis of naphthalene and tetrahydronaphthalene derivatives is described.

  在非极性溶剂（甲苯、四氯化碳）中，添加TBDMSCl的条件下，螺环氧化环己二烯酮的重排反应最好进行，从而形成苯并[1,3]二恶烷。此外，还描述了将其应用于萘和四氢萘衍生物的合成过程。
• Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies
  作者：Giovanni D. Andreetti、Volker Boehmer、J. Graham Jordon、Moniralsadat Tabatabai、Franco Ugozzoli、Walter Vogt、Artur Wolff

  DOI：10.1021/jo00067a040

  日期：1993.7

  Six dissymmetric calix[4]arenes with C4 symmetry consisting of four 3,4-disubstituted phenolic units have been obtained by condensation of the respective 2- or 6-hydroxymethylated phenols. The regular incorporation of the phenolic units into the macrocycle was established on the basis of H-1 NMR spectra and in one case also by X-ray analysis. One example for a calixarene with C2-symmetry consisting of p-cresol and 3,4-dimethylphenol units in alternating sequence was also prepared. Calixarene 4a consisting of 3,4-dimethylphenol units shows a lower energy barrier (DELTAG(double dagger) = 13.4 kcal/mol) for the cone-to-cone inversion in CDCl3 than p-methylcalix[4]arene (DELTAG(double dagger) = 14.6 kcal/mol). The dissymmetric calixarenes 4 could be conformationally fixed by alkylation of the phenolic hydroxyl group. Due to the equivalence of all four phenolic units, mono- and 1,3-di-derivatives could be obtained in addition to tetra derivatives. A tetraester derivative in the cone conformation, like the parent calix[4]arene, crystallizes as a racemate. In solution these tetraester derivatives exist in a distorted cone conformation with C2 symmetry. Dynamic H-1 NMR spectra reveal an energy barrier of DELTAG(double dagger) = 13.3-13.4 kcal/mol for the C2-to-C2 interconversion with the C4-cone as transition state.