(R)-2-phenethylchroman-4-one

• 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: (R)-2-phenethylchroman-4-one
• 英文别名: (2R)-2-(2-phenylethyl)-2,3-dihydrochromen-4-one
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: JSZHKARAUAIUIV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  水杨酸乙酯 在 quinone-thiourea derivative 正丁基锂 、 4 A molecular sieve 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 58.5h， 生成 (R)-2-phenethylchroman-4-one
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of Flavanones and Chromanones

  摘要：

  The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a beta-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the beta-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.

  DOI：

  10.1021/ja070394v

文献信息

• Catalytic asymmetric conjugate addition of Grignard reagents to chromones
  作者：Carlos Vila、Valentín Hornillos、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1039/c3cc43105c

  日期：——

  highly regio- and enantioselective copper catalysed direct conjugate addition of Grignard reagents to chromones has been developed taking advantage of the reduced reactivity of the resulting magnesium enolates. This methodology tolerates a broad scope of alkyl Grignards including secondary alkyl magnesium reagents as well as functionalised chromones.

  利用所得到的烯醇镁的降低的反应性，已经开发了格尼雅试剂向色酮的高度区域选择性和对映选择性铜催化的直接共轭加成。这种方法可以耐受各种烷基格氏试剂，包括仲烷基镁试剂以及功能化的色酮。
• Ruthenium-NHC-Catalyzed Asymmetric Hydrogenation of Flavones and Chromones: General Access to Enantiomerically Enriched Flavanones, Flavanols, Chromanones, and Chromanols
  作者：Dongbing Zhao、Bernhard Beiring、Frank Glorius

  DOI：10.1002/anie.201302573

  日期：2013.8.5

  Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O‐heterocycles—flavanones, chromanones, flavanols, and chromanols—by means of an enantioselective Ru/NHC‐catalyzed hydrogenation process (see scheme; NHC=N‐heterocyclic carbene, PCC=pyridinium chlorochromate).

  二到四！现成的黄酮和色酮通过对映选择性Ru / NHC催化的加氢过程有效地转化为四种有价值的O-杂环手性类别-黄酮，色酮，黄烷醇和色醇-参见表; NHC = N-杂环卡宾， PCC =吡啶鎓氯铬酸盐）。
• Asymmetric Synthesis of Flindersiachromanone Using Lipase-catalyzed Reaction
  作者：Masashi Kawasaki、Hikaru Yoshikai、Hiroko Kakuda、Naoki Toyooka、Akira Tanaka、Michimasa Goto、Tadashi Kometani

  DOI：10.3987/com-05-10652

  日期：——

  The (R)- and (S)-enantiomers of flindersiachromanone (2-(2-phenylethyl)-4-chromanone) were synthesized from the enantiomerically pure 1-phenyl-5-hexen-3-ol obtained via the lipase-catalyzed enantioselective transesterification.
• Catalytic Enantioselective Synthesis of Flavanones and Chromanones
  作者：Margaret M. Biddle、Michael Lin、Karl A. Scheidt

  DOI：10.1021/ja070394v

  日期：2007.4.1

  The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a beta-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the beta-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.