methyl (R)-2-(naphthalen-1-yl)propionate | 148932-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (R)-2-(naphthalen-1-yl)propionate
• 英文别名: (-)-(R)-Methyl 2-(1-naphthyl)propionate；(R)-methyl 2-(1-naphthyl)propionate；methyl (2R)-2-naphthalen-1-ylpropanoate
• CAS: 148932-66-5
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: XULIAJSFPSQIKV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (2S)-2-[(4-methylbenzenesulfonyl)oxy]propanoate 在 三氯化铝 作用下， 反应 10.0h， 生成 methyl (R)-2-(naphthalen-1-yl)propionate
  参考文献：
  名称：

  Stereospecific Friedel-Crafts alkylation of aromatic compounds: synthesis of optically active 2- and 3-arylalkanoic esters

  摘要：

  The alkylation of aromatic compounds, such as benzene, toluene, chlorobenzene, and naphthalene, with optically active (S)-alkyl 2-(sulfonyloxy)propionates and (R)-alkyl 3-(sulfonyloxy)butanoates in the presence of AlCl3 afforded optically active (S)-alkyl 2-arylpropionates and (S)-alkyl 3-arylbutanoates in fair to good chemical yields (40-84%) and in good to excellent optical yields (61-97%). As usually occurs in Friedel-Crafts alkylation reactions, poor regioselectivity was observed.

  DOI：

  10.1021/jo00001a037

文献信息

• Catalytic Enantioselective Protonation of Lithium Ester Enolates Generated by Conjugate Addition of Arylthiolate to Enoates
  作者：Katsumi Nishimura、Masashi Ono、Yasuo Nagaoka、Kiyoshi Tomioka

  DOI：10.1002/1521-3773(20010119)40:2<440::aid-anie440>3.0.co;2-a

  日期：2001.1.19

  A chiral ligand, a catalytic amount of lithium cation, and no chiral proton source: These are features of the present asymmetric addition-protonation of propenoates with 2-trimethylsilylbenzenethiol. The reaction is catalyzed by a combination of lithium 2-trimethylsilylbenzenethiolate and the chiral ligand 1. Desulfurization of the product affords 2-substituted propanoates with high ee values and without

  手性配体，催化量的锂阳离子和无手性质子源：这些是本酸酯与2-三甲基甲硅烷基苯硫醇的不对称加成质子化的特征。该反应由2-三甲基甲硅烷基苯硫醇锂和手性配体1的组合催化。产物的脱硫得到具有高ee值且没有外消旋作用的2-取代的丙酸酯。此外，可以定量地回收1以便重新使用。
• Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
  作者：Florence Malmedy、Thomas Wirth

  DOI：10.1002/chem.201603022

  日期：2016.11.2

  The first stereoselective version of an iodine(III)‐mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α‐arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid‐based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

  描述了在原酸酯存在下碘（III）介导的芳基酮重排的第一个立体选择性形式。反应产物α-芳基化酯是生物活性化合物（如布洛芬）合成中非常有用的中间体。使用基于手性乳酸的碘（III）试剂，产品选择性高达73％  ee。
• An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters
  作者：Zhiyan Huang、Zheng Liu、Jianrong (Steve) Zhou

  DOI：10.1021/ja2066829

  日期：2011.10.12

  asymmetric α-arylation of carbonyl compounds, formation of tertiary centers with high enantioselectivity is a longstanding problem, due to easy enolization of the monoarylation products. Herein, we report such examples using a palladium catalyst supported by a new, (R)-H(8)-BINOL-derived monophosphine. Silyl ketene acetals, together with a weakly basic activator, were used as equivalents of ester anions

  在过渡金属催化的羰基化合物的不对称α-芳基化中，由于单芳基化产物容易烯醇化，形成具有高对映选择性的三级中心是一个长期存在的问题。在此，我们报告了使用由新的 (R)-H(8)-BINOL 衍生的单膦支持的钯催化剂的示例。甲硅烷基乙烯酮缩醛与弱碱性活化剂一起用作酯阴离子的等价物，它们与芳基三氟甲磺酸酯以优异的对映体过量 (ee) 顺利反应。该反应的有效性在 92% ee 的 (S)-萘普生的克级合成中得到证明。
• Pd/Josiphos-Catalyzed Enantioselective α-Arylation of Silyl Ketene Acetals and Mechanistic Studies on Transmetalation and Enantioselection
  作者：Kenya Kobayashi、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1021/om200945q

  日期：2011.11.28

  5-MePh)2PF-Pcy2) catalyzed the enantioselective arylation of silyl ketene acetals with iodoarenes in the presence of TlOAc to promote transmetalation of silyl ketene acetals. The highest enantioselectivities giving α-arylesters up to 91% ee were achieved when (E)-1-methoxy-1-(trimethylsiloxy)propene (E/Z = 88/12) was used for the silyl ketene acetal. The effect on enantioselection of a chiral ligand is discussed

  在TlOAc存在下，钯/（4-MeO-3,5-MePh）2 PF-Pcy 2）催化硅烷基乙烯酮缩醛与碘芳烃的对映选择性芳基化，以促进硅烷基乙烯酮缩醛的金属转移。当将（E）-1-甲氧基-1-（三甲基甲硅烷氧基）丙烯（E / Z = 88/12）用于甲硅烷基烯酮缩醛时，可获得最高91％ee的α-芳基酯的最高对映选择性。基于钯/（4-MeO-3,5-MePh）2 PF-Pcy 2）配合物的X射线结构以及DFT在机械方面的计算研究结果，讨论了对手性配体对映体选择的影响催化循环。
• Stereospecific Friedel-Crafts alkylation of aromatic compounds: synthesis of optically active 2- and 3-arylalkanoic esters
  作者：Oreste Piccolo、Ugo Azzena、Giovanni Melloni、Giovanna Delogu、Ermanno Valoti

  DOI：10.1021/jo00001a037

  日期：1991.1

  The alkylation of aromatic compounds, such as benzene, toluene, chlorobenzene, and naphthalene, with optically active (S)-alkyl 2-(sulfonyloxy)propionates and (R)-alkyl 3-(sulfonyloxy)butanoates in the presence of AlCl3 afforded optically active (S)-alkyl 2-arylpropionates and (S)-alkyl 3-arylbutanoates in fair to good chemical yields (40-84%) and in good to excellent optical yields (61-97%). As usually occurs in Friedel-Crafts alkylation reactions, poor regioselectivity was observed.