(4-bromophenyl)methyl (E)-2-oxo-4-phenylbut-3-enoate | 1112238-38-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4-bromophenyl)methyl (E)-2-oxo-4-phenylbut-3-enoate
• CAS: 1112238-38-6
• 化学式: C₁₇H₁₃BrO₃
• 分子量: 345.192
• InChiKey: OZLRGTDZCUQNLS-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基-2-苯基-2-噁唑啉-5-酮 、 (4-bromophenyl)methyl (E)-2-oxo-4-phenylbut-3-enoate 在 4-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(naphthalen-1-ylmethoxy)methyl]quinolin-6-ol 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以96%的产率得到(4R,5S)-4-bromobenzyl 5-benzamido-5-methyl-6-oxo-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylate
  参考文献：
  名称：

  Bifunctional cinchona alkaloids-catalyzed asymmetric [4+2] cycloaddition reaction of β,γ-unsaturated α-keto esters with oxazolones

  摘要：

  A highly enantioselective [4+2] cycloaddition reaction of beta,gamma-unsaturated alpha-keto esters with oxazolones was realized with readily available cinchona alkaloids as the catalysts. Using this reaction, a series of highly functionalized delta-lactones with adjacent alpha-quaternary-beta-tertiary stereocenters were obtained in high yields (up to 97%) and with good-to-excellent enantioselectivities (up to 97% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.069

文献信息

• An unexpected tandem enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β,γ-unsaturated α-keto esters catalyzed by cinchona alkaloids
  作者：Hai-Feng Wang、Chang-Wu Zheng、Ying-Quan Yang、Zhuo Chai、Gang Zhao

  DOI：10.1016/j.tetasy.2008.11.007

  日期：2008.11

  Cinchona alkaloids were found to catalyze an enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β,γ-unsaturated α-keto esters 1 and malonates 2. Using the optimum catalyst quinine 4a, a series of the rearranged products 3 were obtained with up to 98% yield and 82% ee under mild reaction conditions.

  发现金鸡纳生物碱催化β，γ-不饱和α-酮酯1和丙二酸酯2的对映选择性迈克尔加成/氧合亲核重排反应。使用最佳催化剂奎宁4a，在温和的反应条件下获得了一系列重排产物3，产率高达98％，ee达到82％。
• Efficient Enantioselective Synthesis of Dihydropyrans Using a Chiral <i>N</i>,<i>N</i>′-Dioxide as Organocatalyst
  作者：Juhua Feng、Xuan Fu、Zhenling Chen、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/ol400894j

  日期：2013.6.7

  The bifunctional organocatalyst C3 N,N'-dioxide has been successfully applied to the asymmetric cascade Michael/hemiacetalization reaction of alpha-substituted cyano ketones and beta,gamma-unsaturated alpha-ketoesters for the synthesis of multifunctionalized chiral dihydropyrans. The corresponding products were obtained in excellent yields (up to 99%) with high to excellent enantioselectivities (up to 99% ee).
• Bifunctional cinchona alkaloids-catalyzed asymmetric [4+2] cycloaddition reaction of β,γ-unsaturated α-keto esters with oxazolones
  作者：Yin Ying、Zhuo Chai、Hai-Feng Wang、Peng Li、Chang-Wu Zheng、Gang Zhao、Yue-Peng Cai

  DOI：10.1016/j.tet.2011.03.069

  日期：2011.5

  A highly enantioselective [4+2] cycloaddition reaction of beta,gamma-unsaturated alpha-keto esters with oxazolones was realized with readily available cinchona alkaloids as the catalysts. Using this reaction, a series of highly functionalized delta-lactones with adjacent alpha-quaternary-beta-tertiary stereocenters were obtained in high yields (up to 97%) and with good-to-excellent enantioselectivities (up to 97% ee). (C) 2011 Elsevier Ltd. All rights reserved.