1-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene | 199442-39-2

• 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-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: 7-Methoxy-2-methyl-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 199442-39-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: SRDJZYVMYHXTOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene 在 三溴化磷 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.5h， 生成 7-甲基-2-萘酚
  参考文献：
  名称：

  Deleterious effect of 7-methyl group on glycosylation of 2-naphthols

  摘要：

  C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (I). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.045
• 作为产物：
  描述：

  3,4-dihydro-7-methoxy-2-methylnaphthalen-1(2H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以73%的产率得到1-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  滑动环己烷重排

  摘要：

  可以通过四氯化锆的作用将6-甲氧基四氢化萘转化为8-甲氧基四氢化萘。尽管周转缓慢，但产量总体上还是不错的。超声辐射，相转移催化剂，冠醚和氯化锂都可加速反应，该反应通过C-1至C-8a键的断裂和分子内Friedel-Crafts烷基化环化而进行。

  DOI：

  10.1016/s0040-4020(97)10014-x

文献信息

• The sliding cyclohexane rearrangement
  作者：David C Harrowven、Richard F Dainty

  DOI：10.1016/s0040-4020(97)10014-x

  日期：1997.11

  transformed into 8-methoxytetralins through the action of zirconium tetrachloride. Yields are generally good though turnover is slow. Ultrasonic irradiation, phase transfer catalysts, crown ethers and lithium chloride all accelerate the reaction which proceeds via scission of the C-1 to C-8a bond and cyclisation by intramolecular Friedel-Crafts alkylation.

  可以通过四氯化锆的作用将6-甲氧基四氢化萘转化为8-甲氧基四氢化萘。尽管周转缓慢，但产量总体上还是不错的。超声辐射，相转移催化剂，冠醚和氯化锂都可加速反应，该反应通过C-1至C-8a键的断裂和分子内Friedel-Crafts烷基化环化而进行。
• Direct Synthesis of <i>Gem</i>-β,β′-Bis(alkyl) Alcohols Using Nickel Catalysis via Sequential DCR Approach
  作者：Lalit Mohan Kabadwal、Atanu Bera、Debasis Banerjee

  DOI：10.1021/acscatal.4c00647

  日期：2024.3.15

  functionalized gem-β,β′-bis(alkyl)alcohols by coupling of a β-alkylated secondary alcohol with a primary alcohol is reported using nickel via sequential DCR (dehydrogenation–condensation–rehydrogenation) approach. Using our method, 1-arylethanol and benzyl alcohols undergo a one-pot successive double alkylation reaction to form functionalized alcohols. Methanol, C2–C12 alcohols, citronellol, and fatty acid-derived

  据报道，使用镍通过连续 DCR（脱氢-缩合-再氢化）方法，通过将 β-烷基化仲醇与伯醇偶联来化学选择性合成功能化 gem-β,β'-双（烷基）醇。使用我们的方法，1-芳基乙醇和苯甲醇进行一锅连续双烷基化反应，形成官能化醇。可以耐受甲醇、C2-C12 醇、香茅醇和脂肪酸衍生的油醇，包括类固醇激素（胆固醇和睾酮）和 5-pregnen-3β-ol-20-one 的后期功能化。催化转化能够合成多奈哌齐药物（用于治疗阿尔茨海默病）、N-杂芳烃（喹啉和吖啶），包括色烷和中间黄烷衍生物。对不同对位取代的苯甲醇与 1-苯基丙醇的哈米特动力学图分析表明，苯甲醇的氧化可能是速率决定步骤，并且预计取代对反应动力学有强烈影响。负ρ值 (-0.60) 强烈表示苯甲醇上形成正电荷。初步机理研究表明，醇脱氢为醛是决定速率的步骤，因为它涉及醇的 C-H/D 键断裂，计算出的P H / P D值为 6.0。反应曲线研究、EPR
• Deleterious effect of 7-methyl group on glycosylation of 2-naphthols
  作者：Prithiba Mitra、Subhajit Mandal、Soumen Chakraborty、Dipakranjan Mal

  DOI：10.1016/j.tet.2015.06.045

  日期：2015.8

  C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (I). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols. (C) 2015 Elsevier Ltd. All rights reserved.