(S,E)-2-acetyl-2-(3-(4-fluorophenyl)allyl)-3,4-dihydronaphthalen-1(2H)-one | 1440773-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S,E)-2-acetyl-2-(3-(4-fluorophenyl)allyl)-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: (1E,2S)-2-acetyl-2-(3-(4-fluorophenyl)allyl)-3,4-dihydronaphthalen-1(2H)-one；(2S)-2-acetyl-2-[(E)-3-(4-fluorophenyl)prop-2-enyl]-3,4-dihydronaphthalen-1-one
• CAS: 1440773-74-9
• 化学式: C₂₁H₁₉FO₂
• 分子量: 322.379
• InChiKey: GMUXEPDOIXZRAH-KTBYTZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰-1-四酮 、 (E)-3-(4-fluorophenyl)allyl acetate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (2S,5S)-naphthalen-1-ylmethyl 1-(dinaphtho[2,1-d:1’,2’-f][1,3,2]dioxaphosphep-in-4-yl)-5-phenylpyrrolidine-2-carboxylate 、 lithium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以97%的产率得到(S,E)-2-acetyl-2-(3-(4-fluorophenyl)allyl)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  A New Class of Non-C₂-Symmetric Ligands for Oxidative and Redox-Neutral Palladium-Catalyzed Asymmetric Allylic Alkylations of 1,3-Diketones

  摘要：

  We report the discovery, synthesis, and application of a new class of non-C-2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.

  DOI：

  10.1021/jacs.5b00786

文献信息

• Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
  作者：Barry M. Trost、David A. Thaisrivongs、Etienne J. Donckele

  DOI：10.1002/anie.201207870

  日期：2013.1.28

  reaction with 2‐acetyl‐1‐tetralones to form quaternary carbon stereocenters. This is a conceptually and mechanistically distinct strategy from traditional methods for the synthesis of enantioenriched allylic substitution products. 2,6‐DMBQ=2,6‐dimethylbenzoquinone.

  一类新的配体：通过发现一类新的亚磷酰胺配体，使标题反应成为可能。各种空间和电子上不同的烯丙基芳烃与2-乙酰基-1-四氢萘酮反应形成季碳立体中心。这是与传统方法在概念和机械上截然不同的策略，用于合成对映体富集的烯丙基取代产物。2,6-DMBQ = 2,6-二甲基苯醌。
• A New Class of Non-<i>C</i>₂-Symmetric Ligands for Oxidative and Redox-Neutral Palladium-Catalyzed Asymmetric Allylic Alkylations of 1,3-Diketones
  作者：Barry M. Trost、Etienne J. Donckele、David A. Thaisrivongs、Maksim Osipov、James T. Masters

  DOI：10.1021/jacs.5b00786

  日期：2015.2.25

  We report the discovery, synthesis, and application of a new class of non-C-2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.