(2S)-(7-methoxy-4-oxo-chroman-3-yl)-acetic acid ethyl ester | 1016976-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S)-(7-methoxy-4-oxo-chroman-3-yl)-acetic acid ethyl ester
• 英文别名: ethyl (S)-2-(7-methoxy-4-oxochroman-3-yl)acetate；ethyl 2-[(3S)-7-methoxy-4-oxo-2,3-dihydrochromen-3-yl]acetate
• CAS: 1016976-53-6
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: QKFZWGPNVLJSQS-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 4-(2-formyl-5-methoxyphenoxy)but-2-enoate 在 C₁₈H₁₇F₅N₃O⁽¹⁺⁾*C₂₄H₂₀B^(1-) 、 N,N-二异丙基乙胺 作用下， 以 环己烷 为溶剂， 反应 20.0h， 以95%的产率得到(2S)-(7-methoxy-4-oxo-chroman-3-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  新型（-）-β-P烯衍生的三唑盐：合成及其在不对称Stetter反应中的应用

  摘要：

  合成了一系列从（-）-β-pine烯衍生的新型手性三唑鎓盐，发现它们是对映选择性分子内Stetter反应的高效预催化剂。由单一前体（-）-β-pine烯制得的三唑鎓盐在Stetter反应中与对映体对面的脸部选择性反应，以优异的收率和优异的立体选择性提供单，二和三取代的苯并二氢呋喃酮。

  DOI：

  10.1002/cctc.201600498

文献信息

• Mechanistic Investigation of the Enantioselective Intramolecular Stetter Reaction: Proton Transfer Is the First Irreversible Step
  作者：Jennifer L. Moore、Anthony P. Silvestri、Javier Read de Alaniz、Daniel A. DiRocco、Tomislav Rovis

  DOI：10.1021/ol200256a

  日期：2011.4.1

  A study on the mechanism of the asymmetric intramolecular Stetter reaction is reported. This investigation includes the determination of the rate law, kinetic isotope effects, and competition experiments. The reaction was found to be first order in aldehyde and azolium catalyst or free carbene. A primary kinetic isotope effect was found for the proton of the aldehyde. Taken together with a series of

  报道了对不对称分子内 Stetter 反应机理的研究。该调查包括速率定律的确定、动力学同位素效应和竞争实验。发现反应在醛和唑鎓催化剂或游离卡宾中是一级反应。发现了醛质子的主要动力学同位素效应。结合一系列竞争实验，这些结果表明，从卡宾亲核攻击形成的四面体中间体到醛上的质子转移是第一个不可逆的步骤。
• Scope of the Asymmetric Intramolecular Stetter Reaction Catalyzed by Chiral Nucleophilic Triazolinylidene Carbenes
  作者：Javier Read de Alaniz、Mark S. Kerr、Jennifer L. Moore、Tomislav Rovis

  DOI：10.1021/jo702313f

  日期：2008.3.1

  A highly enantioselective intramolecular Stetter reaction of aromatic and aliphatic aldehydes tethered to different Michael acceptors has been developed. Two triazolium scaffolds have been identified that catalyze the intramolecular Stetter reaction with good reactivity and enantioselectivity. The substrate scope has been examined and found to be broad; both electron-rich and -poor aromatic aldehydes

  芳香族和脂肪族醛与不同迈克尔受体的高度对映选择性分子内 Stetter 反应已被开发出来。已鉴定出两种三唑鎓支架以良好的反应性和对映选择性催化分子内 Stetter 反应。底物范围已经过检查，发现范围很广；富电子和贫电子芳香醛均以高产率和对映选择性进行环化。系链可以包括氧、硫、氮和碳连接体而没有不利影响。此外，各种束缚迈克尔受体的结合包括酰胺、酯、硫酯、酮、醛和腈。催化剂负载量可以降低到 3 mol%，而不会显着影响反应的反应性或选择性。
• Design and synthesis of novel chiral dihydroimidazolium cyclophanes as N-heterocyclic carbene precatalysts
  作者：Ting Lu、Liuqun Gu、Qiang Kang、Yugen Zhang

  DOI：10.1016/j.tetlet.2012.09.116

  日期：2012.11

  A series of novel diphenyl ethylenediamine (DPEN) derived C-2 symmetric dihydroimidazolium cyclophanes were designed and synthesized as organo NHC precatalysts. The resultant organo NHC-catalyzed reactions with superior enantioselectivity than traditional C-2 dihydroimidazolidine NHCs as exemplified by NHC-catalyzed asymmetric intramolecular Stetter reactions. (C) 2012 Elsevier Ltd. All rights reserved.
• An asymmetric intramolecular Stetter reaction catalyzed by a chiral triazolium precatalyst bearing a pyridine moiety
  作者：Takahiro Soeta、Yuhta Tabatake、Yutaka Ukaji

  DOI：10.1016/j.tet.2012.09.095

  日期：2012.12

  A number of chiral triazolium salts incorporating pyridine rings have been investigated as precatalysts for an asymmetric intramolecular Stetter reaction. The salt structure and reaction parameters were optimized, resulting in very good yield and enantioselectivity. This reaction was found to be applicable to a wide range of salicylaldehyde-derived substrates. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel (−)-β-Pinene-Derived Triazolium Salts: Synthesis and Application in the Asymmetric Stetter Reaction
  作者：Zbigniew Rafiński

  DOI：10.1002/cctc.201600498

  日期：2016.8.22

  from (−)‐β‐pinene were synthesized and found to be highly efficient precatalysts for the enantioselective intramolecular Stetter reaction. The triazolium salts prepared from a single precursor, (−)‐β‐pinene, react with antipodal enantiofacial selectivity in the Stetter reaction to afford mono‐, di‐, and trisubstituted chromanones in excellent yields with excellent stereoselectivity.

  合成了一系列从（-）-β-pine烯衍生的新型手性三唑鎓盐，发现它们是对映选择性分子内Stetter反应的高效预催化剂。由单一前体（-）-β-pine烯制得的三唑鎓盐在Stetter反应中与对映体对面的脸部选择性反应，以优异的收率和优异的立体选择性提供单，二和三取代的苯并二氢呋喃酮。