6-methoxy-1-methyl-1,2,3,4-tetrahydronaphthalene | 1730-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-methoxy-1-methyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: tetrahydro-6-methoxy-1-methylnaphthalene；6-methoxy-1-methyltetralin；methyl-(5-methyl-5,6,7,8-tetrahydro-[2]naphthyl)-ether；Methyl-(5-methyl-5,6,7,8-tetrahydro-[2]naphthyl)-aether；1-methyl-6-methoxy-tetralin
• CAS: 1730-57-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: ZWHPNHBMKJDFAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-1-methyl-1,2,3,4-tetrahydronaphthalene 在 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以66%的产率得到7-methoxy-4-methyl-1,2-dihydronaphthalene
  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
• 作为产物：
  描述：

  6-methoxy-1-methylene-1,2,3,4-tetrahydronaphthalene 在 铂 氢气 作用下， 以 甲醇 为溶剂， 生成 6-methoxy-1-methyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Moreau,C.; Rouessac,F., Bulletin de la Societe Chimique de France, 1973, p. 3427 - 3432

  摘要：

  DOI：

文献信息

• Benzylic C(sp³)–H Functionalization for C–N and C–O Bond Formation via Visible Light Photoredox Catalysis
  作者：Ganesh Pandey、Ramkrishna Laha、Deepak Singh

  DOI：10.1021/acs.joc.6b00970

  日期：2016.8.19

  A visible light mediated highly selective benzylic C–H bond functionalization for intermolecular C–N and C–O bond formation is reported. This cross-dehydrogenative coupling reaction demonstrates a straightforward protocol for incorporating the heteroaromatics to the benzylic position. Benzylic oxidation of various alkyl aryls to corresponding carbonyl compounds has also been reported.

  可见光介导的高选择性苄基CH键对分子间CN和CO键形成的作用。该交叉脱氢偶联反应证明了将杂芳族化合物并入苄基位置的简单方法。也已经报道了各种烷基芳基被苄基氧化为相应的羰基化合物。
• Zwitterionic Iridium Complexes with P,N-Ligands as Catalysts for the Asymmetric Hydrogenation of Alkenes
  作者：Axel Franzke、Andreas Pfaltz

  DOI：10.1002/chem.201003314

  日期：2011.4.4

  Several zwitterionic iridium complexes based on chiral P,N‐ligands with imidazoline or oxazoline donors and anionic tetraarylborate or aryltrifluoroborate substituents have been synthesized. The corresponding cationic analogues have also been prepared, to evaluate the effect of the covalent linkage between the anion and the cationic metal complex in catalytic reactions. The respective pairs of structurally

  已经合成了几种基于手性P，N-配体与咪唑啉或恶唑啉供体以及阴离子四芳基硼酸酯或芳基三氟硼酸酯取代基的两性离子铱配合物。还制备了相应的阳离子类似物，以评估阴离子与阳离子金属络合物之间的共价键在催化反应中的作用。已经比较了各对结构类似的预催化剂在未官能化烯烃的不对称氢化中的功效。在大多数情况下，阴离子衍生化实际上对铱络合物的不对称诱导没有影响。这与X射线结构研究一致，该研究表明，阳离子金属中心的手性环境不受阴离子取代基的影响。
• Asymmetric hydrogenation of aromatic olefins catalyzed by iridium complexes of proline derived phosphine–oxazoline ligands
  作者：Guopin Xu、Scott R. Gilbertson

  DOI：10.1016/s0040-4039(02)02747-8

  日期：2003.1

  phosphine–oxazoline ligands is reported. This ligands are synthesized by reaction of a phosphine chloride with the secondary nitrogen of proline. Upon coordination to iridium the resulting complexes can be used in the asymmetric hydrogenation of simple olefins. The effect of different counter ions and substitution at the oxazoline and the phosphine is reported.

  报道了一系列膦-恶唑啉配体的合成。该配体通过氯化膦与脯氨酸的仲氮反应合成。与铱配位后，所得络合物可用于简单烯烃的不对称氢化。报道了不同的​​抗衡离子和在恶唑啉和膦处的取代作用。
• Chiral ligands
  申请人：Solvias AG

  公开号：EP2202236A1

  公开（公告）日：2010-06-30

  Chiral compounds of the formula (1), which are optically pure or highly optically enriched in which R0 is C1-C12-alkyl which is unsubstituted or substituted by 1 to 2 C1-C4-alkoxy; cyclopentyl or cyclohexyl, which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl or C1-C4-alkoxy; or benzyl, phenyl or naphtyl which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl or C1-C4-fluoroalkoxy, F or Cl, each of R1 and R'1 independently is hydrogen or has the meaning of R0 whereby R1, R'1 and R0 can be same or different, R2 and R3 are independently a C-bonded hydrocarbon radical or a heterohydrocarbon radical, and each of both R4 is C1-C6-alkyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, methylbenzyl or benzyl, or both R4 together form an aliphatic C4-C6 carbocycle. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reaction, particularly hydrogenations.

  化学式（1）的手性化合物，其光学纯度高或光学富集，其中R0是未取代或取代1至2个C1-C4-烷氧基的C1-C12-烷基；环戊基或环己基，未取代或取代1至3个C1-C4-烷基或C1-C4-烷氧基；或苄基，苯基或萘基，未取代或取代1至3个C1-C4-烷基，C1-C4-烷氧基，C1-C4-氟烷基或C1-C4-氟烷氧基，F或Cl，R1和R'1中的每一个独立地是氢或具有R0的含义，其中R1，R'1和R0可以相同也可以不同，R2和R3独立地是C键合的碳氢基团或杂原子碳氢基团，R4中的每一个都是C1-C6-烷基，环戊基，环己基，苯基，甲基苯基，甲基苄基或苄基，或者两个R4一起形成一个脂肪族C4-C6碳环。这些配体的金属络合物是对不对称加成反应，尤其是氢化反应的均相催化剂。
• A novel skeletal rearrangement of bicyclo(2.2.2)octenes through bicyclo(3.2.1)octene system: synthesis of (±)-hinesol and (±)-10--hinesol
  作者：G.S.R.Subba Rao、Seenivasaga N Janaki

  DOI：10.1016/0040-4039(88)85097-4

  日期：1988.1

  Acid catalysed rearrangement of the -alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties. An efficient entry into spiro(4.5)decane and eremane system, as exemplified by the total synthesis of (±)-hinesol (2) and its 10-epimer (3) is reported.

  -醇（9）的酸催化重排导致具有双环（3.2.1）和双环（2.2.2）部分的酮（11）和（12）。据报道，可以高效地进入螺（4.5）癸烷和乙二胺系统，以（±）-海因溶胶（2）及其10-受体（3）的全合成为例。