(9R)-1-(methoxyethyl)anthracene | 901773-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (9R)-1-(methoxyethyl)anthracene
• 英文别名: (R)-9-(1-methoxyethyl)anthracene；9-(1-(1R)-methoxyethyl)anthracene；9-[(1R)-1-methoxyethyl]anthracene
• CAS: 901773-16-8
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: SJGPOUFALJZJIS-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (9R)-1-(methoxyethyl)anthracene 、 N-(4-硝基苯基)马来酰亚胺 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到(3aR,9aR)-3a,4,9,9a-tetrahydro-4-[(1R)-1-methoxyethyl]-2-(N-4'-nitrophenyl)-4,9-[1',2']benzeno-1H-benzo[f]isoindole-1,3-(2H)-dione
  参考文献：
  名称：

  Diastereoselective Cycloadditions and Transformations ofN-Alkyl andN-Aryl Maleimides with Chiral 9-Anthrylethanol Derivatives

  摘要：

  Thermal Diels-Alder reactions of chiral 9-methoxyethyl and 9-hydroxyethyl anthracene have been investigated both experimentally and computationally with a range of N-substituted maleimides. Whereas cycloadditions with 9-methoxyethyl anthracene proceeded with almost complete diastereselectivity, those with 1-anthracenc-9-yl-ethanol resulted in essentially no diastereoselectivity. Subsequent regio- and stereoselective transformations with reducing agents and carbon nucleophiles demonstrated the synthetic utility of this methodology, which was applied to the enantioselective synthesis of pyrrolo[2,1-a]isoquinolines and an attempted synthesis of the alkaloid crispine A. Computational studies supported the proposed hypotheses for the stereoselectivity observed in the transformations described.

  DOI：

  10.1021/jo101437b
• 作为产物：
  描述：

  (4aS,9aR)-4a,9,9a,10-tetrahydro-9-[(1R)-1-methoxyethyl]-9,10-[1',2']-benzenoanthracene-1,4-dione 以 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到(9R)-1-(methoxyethyl)anthracene
  参考文献：
  名称：

  9R-（1-甲氧基乙基）蒽与对苯醌的非对映选择性Diels-Alder环加成反应。

  摘要：

  当在二甲苯中加热回流时，对苯醌与9R-（1-甲氧基乙基）蒽的Diels-Alder环加成反应可提供60:40的环加合物比率。探索这种选择性起源的机理研究表明，在较低温度下，动力学产物占主导地位，环加合物的比率为96：4。

  DOI：

  10.1039/b603819k

文献信息

• A tandem asymmetric synthesis approach for the efficient preparation of enantiomerically pure 9-(hydroxyethyl) anthracene
  作者：Jennifer C. Ball、Paul Brennan、Tareg M. Elsunaki、Alexis Jaunet、Simon Jones

  DOI：10.1016/j.tetasy.2011.01.019

  日期：2011.2

  A tandem approach for the preparation of gram quantities of enantiomerically pure 9-(hydroxyethyl)-anthracene is presented using an asymmetric reduction followed by kinetic resolution that has potential applicability to other chiral alcohols.

  提出了一种串联方法，用于制备克量的对映体纯的9-（羟乙基）-蒽，方法是不对称还原，随后进行动力学拆分，该动力学拆分对其他手性醇具有潜在的适用性。
• Synthesis of quaternary stereogenic centres via stereoselective intermolecular Friedel–Crafts reactions
  作者：Jennifer C. Ball、Robert Gleave、Simon Jones

  DOI：10.1039/c1ob05129f

  日期：——

  Highly stereoselective Friedel–Crafts reactions have been performed using a chiral anthracene template to control the selectivity of the reaction. In the case of additions to fully substituted N-acyliminium ions, competitive elimination and condensation reactions were observed. Retro-Diels–Alder reaction of one of the reaction products led to a precursor that could be used for the construction of pyroglutamic

  使用手性蒽模板进行了高度立体选择性的Friedel-Crafts反应，以控制反应的选择性。在添加到完全取代的N-酰基亚胺离子的情况下，观察到竞争性消除和缩合反应。其中一种反应产物的Retro-Diels-Alder反应产生了一种前体，可用于构建带有季位立体中心的焦谷氨酸。
• Diastereoselective Cycloadditions and Transformations of<i>N</i>-Alkyl and<i>N</i>-Aryl Maleimides with Chiral 9-Anthrylethanol Derivatives
  作者：Harry Adams、Tareg M. Elsunaki、Isaac Ojea-Jiménez、Simon Jones、Anthony J. H. M. Meijer

  DOI：10.1021/jo101437b

  日期：2010.9.17

  Thermal Diels-Alder reactions of chiral 9-methoxyethyl and 9-hydroxyethyl anthracene have been investigated both experimentally and computationally with a range of N-substituted maleimides. Whereas cycloadditions with 9-methoxyethyl anthracene proceeded with almost complete diastereselectivity, those with 1-anthracenc-9-yl-ethanol resulted in essentially no diastereoselectivity. Subsequent regio- and stereoselective transformations with reducing agents and carbon nucleophiles demonstrated the synthetic utility of this methodology, which was applied to the enantioselective synthesis of pyrrolo[2,1-a]isoquinolines and an attempted synthesis of the alkaloid crispine A. Computational studies supported the proposed hypotheses for the stereoselectivity observed in the transformations described.
• Highly diastereoselective Diels–Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone
  作者：Harry Adams、Simon Jones、Isaac Ojea-Jimenez

  DOI：10.1039/b603819k

  日期：——

  Diels-Alder cycloadditions of p-benzoquinone with 9R-(1-methoxyethyl)anthracene provides a 60:40 ratio of cycloadducts when heated at reflux in xylene. Mechanistic studies to explore the origins of this selectivity have shown that at lower temperatures the kinetic product predominates, giving a 96:4 ratio of cycloadducts.

  当在二甲苯中加热回流时，对苯醌与9R-（1-甲氧基乙基）蒽的Diels-Alder环加成反应可提供60:40的环加合物比率。探索这种选择性起源的机理研究表明，在较低温度下，动力学产物占主导地位，环加合物的比率为96：4。