(R)-7-methoxy-1-methyl-1-vinyl-1,2,3,4-tetrahydronaphthalene | 161693-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-7-methoxy-1-methyl-1-vinyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: (S)-1-Vinyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene；(4R)-4-ethenyl-6-methoxy-4-methyl-2,3-dihydro-1H-naphthalene
• CAS: 161693-43-2
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: RQPUJJNSGGUFEL-AWEZNQCLSA-N

物化性质

• 沸点：
  283.1±39.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (R)-7-methoxy-1-methyl-1-vinyl-1,2,3,4-tetrahydronaphthalene 在 Wilkinson's catalyst sodium hydroxide 、 草酰氯 、 双氧水 、 二甲基亚砜 、 三乙胺 、 儿萘酚硼烷 作用下， 反应 26.0h， 生成 (R)-2-(7-methoxy-1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)acetaldehyde
  参考文献：
  名称：

  Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine

  摘要：

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.

  DOI：

  10.1021/jo00110a033
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 palladium on activated charcoal 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 吡啶 、 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 四丁基氟化铵 、 氢气 、 溴 、 lithium carbonate 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三乙胺 、 三氟甲烷磺酸甲酯 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 145.42h， 生成 (R)-7-methoxy-1-methyl-1-vinyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine

  摘要：

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.

  DOI：

  10.1021/jo00110a033

文献信息

• Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers
  作者：T. RajanBabu、Craig Smith、Hwan Lim、Aibin Zhang

  DOI：10.1055/s-0029-1216826

  日期：2009.6

  2′-biphenol are almost as good as ligands derived from the more expensive enantiopure 1,1′-bi(2-naphthol)s. The hydrovinylation products, which carry two versatile latent functionalities, an aryl and a vinyl group, are potentially useful for the synthesis of several important natural products containing benzylic all-carbon quaternary centers. alkenes - asymmetric catalysis - hydrovinylation - phosphoramidite

  α-烷基苯乙烯在由 [(烯丙基)NiBr] 2、Na + [BAr 4 ] - [Ar = 3,5-双(三氟甲基)苯基]制备的镍催化剂存在下进行有效的加氢乙烯基化（添加乙烯），并且亚磷酰胺配体以优异的产率和对映选择性提供产品。在许多情况下，衍生自非手性 2,2'-双酚的亚磷酰胺几乎与衍生自更昂贵的对映体纯 1,1'-双（2-萘酚）的配体一样好。氢乙烯基化产物带有两个通用的潜在官能团，一个芳基和一个乙烯基，可用于合成几种含有苄基全碳季中心的重要天然产物。 烯烃 - 不对称催化 - 加氢乙烯基化 - 亚磷酰胺配体 - 镍
• Ethylene in Organic Synthesis: A New Route to Anticholenergic Pyrrolidinoindolines, and Other Molecules with All Carbon-Quaternary Centers via Asymmetric Hydrovinylation
  作者：Hwan Jung Lim、T. V. RajanBabu

  DOI：10.1021/ol203052y

  日期：2011.12.16

  The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3, 3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.
• Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine
  作者：Alison N. Hulme、Steven S. Henry、A. I. Meyers

  DOI：10.1021/jo00110a033

  日期：1995.3

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.