(-)-2-(4-bromophenyl)chroman-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-2-(4-bromophenyl)chroman-4-one
• 英文别名: (2S)-2-(4-bromophenyl)-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: HFCRUUCITZMIKC-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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 cinchonidine-derived substituted thiourea 哌啶 、 正丁基锂 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 78.5h， 生成 (-)-2-(4-bromophenyl)chroman-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

• Tandem intramolecular oxa-Michael addition/decarboxylation reaction catalyzed by bifunctional cinchona alkaloids: facile synthesis of chiral flavanone derivatives
  作者：Hai-Feng Wang、Hua Xiao、Xiao-Wei Wang、Gang Zhao

  DOI：10.1016/j.tet.2011.05.088

  日期：2011.7

  Bifunctional cinchona alkaloids were used to catalyze a tandem intramolecular oxa-Michael addition/decarboxylation reaction of alkylidene β-ketoesters 1, providing a series of flavanone derivatives with up to 97% yield and 93% ee.

  双功能金鸡纳生物碱用于催化亚烷基β-酮酸酯1的串联分子内氧杂-迈克尔加成/脱羧反应，提供了一系列黄烷酮衍生物，收率高达97％，ee高达93％。
• Enhanced reactivity and selectivity of asymmetric oxa-Michael addition of 2′-hydroxychalcones in carbon confined spaces
  作者：Melad Shaikh、Kiran Kumar Atyam、Mahendra Sahu、Kalluri V. S. Ranganath

  DOI：10.1039/c7cc01096f

  日期：——

  Carbon nanotubes (CNTs) are employed as nanoscale reaction vessels for the asymmetric oxa-Michael addition of 2′-hydroxychalcones.

  碳纳米管（CNTs）被用作纳米级反应容器，用于2'-羟基香豆素的不对称氧-迈克尔加成反应。
• 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.