6-methoxy-3-methyl-1,2-dihydronaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxy-3-methyl-1,2-dihydronaphthalene
• 英文别名: 7-methoxy-2-methyl-3,4-dihydronaphthalene
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: BYXRHTMMZKPYLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-methyl-1,2-dihydronaphthalene 在 三溴化磷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 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 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 12.0h， 生成 6-methoxy-3-methyl-1,2-dihydronaphthalene
  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

文献信息

• Catalytic asymmetric reduction of trisubstituted olefins
  申请人：Massachusetts Institute of Technology

  公开号：US05442119A1

  公开（公告）日：1995-08-15

  A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 1 to 200 atmospheres.

  揭示了一种催化不对称还原过程，通过加氢三取代烯烃，产生具有高对映纯度的相应有机化合物。还原过程利用手性金属催化剂，其中包括从3、4、5或6组、镧系和锕系金属或金属配合物中选择的金属。此外，该过程使用氢作为量化还原剂，可在大约1至200个大气压范围内进行。
• [EN] CATALYTIC ASYMMETRIC REDUCTION OF TRISUBSTITUTED OLEFINS AND ENAMINES<br/>[FR] REDUCTION ASYMETRIQUE CATALYTIQUE D'OLEFINES TRISUBSTITUEES ET D'ENAMINES
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：WO1995002567A1

  公开（公告）日：1995-01-26

  (EN) A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The process is also effective for the catalytic asymmetric reduction of certain enamines and related compounds to yield a corresponding amine or related compound, respectively, having a high level of enantiomeric purity. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 0.5 to 200 atmospheres. The reaction can aslo be carried out using an acidic compound as a rate enhancing additive.(FR) Procédé de réduction asymétrique catalytique qui, par l'hydrogénation d'oléfines trisubstituées, produit un composé organique correspondant présentant un degré élevé de pureté énantiomère. Ledit procédé est également efficace pour la réduction asymétrique catalytique de certaines énamines et de composés apparentés et permet d'obtenir respectivement une amine ou un composé apparenté correspondants, présentant un degré élevé de pureté énantiomère. Ledit procédé de réduction implique l'utilisation d'un catalyseur métallique chiral comprenant un métal ou complexe métallique sélectionnés dans des groupes constitués de 3, 4, 5, ou 6 lanthanides et actinides. De plus, ledit procédé utilise de l'hydrogène en tant qu'agent de réduction stoechiométrique et peut être appliqué à des pressions allant d'environ 0,5 à 200 atmosphères. La réaction peut également être effectuée avec un composé acide en tant qu'additif d'accélération.

  一种催化不对称还原过程，通过氢化三元组烯烃，制备高反 Nap纯度的有机化合物。该过程还有效地用于催化不对称 N达明和相关化合物的还原，制备相应的一胺或相关化合物，同样具有高反 Nap 纯度。还原过程使用含有一种选择自3、4、5或6族、镧系和锕系金属或其复合物的 chiral metal catalyst。此外，过程使用氢作为量度还原剂，并且可以在压力约为0.5至200个大气压下运行。此反应还可以用酸性化合物作为加速增强剂进行操作。
• US5442119A
  申请人：——

  公开号：US5442119A

  公开（公告）日：1995-08-15
• US5491233A
  申请人：——

  公开号：US5491233A

  公开（公告）日：1996-02-13
• 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.