(S)-4-(2-oxo-2-phenylethyl)chroman-2-one | 1403743-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-(2-oxo-2-phenylethyl)chroman-2-one
• 英文别名: (4S)-4-phenacyl-3,4-dihydrochromen-2-one
• CAS: 1403743-67-8
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: FLRIOMDNGFPPHU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetaldehyde 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 邻硝基苯甲酸 、 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 邻二甲苯 、 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到(S)-4-(2-oxo-2-phenylethyl)chroman-2-one
  参考文献：
  名称：

  Enantioselective Formation of Substituted 3,4-Dihydrocoumarins by a Multicatalytic One-Pot Process

  摘要：

  The formation of optically active 3,4-dihydrocoumarins is presented by merging aminocatalysis with an N-heterocyclic carbene-catalyzed internal redox reaction. The products are formed in good to excellent yields and in general with excellent enantioselectivities. Moreover, the developed procedure demonstrates the potential of enantioselective, multicatalytic sequences. By employing an enantiopure aminocatalyst in the enantiodifferentiating step, the challenges related to achieving high stereoinductions by deployment of optically active NHC-catalysts can be circumvented.

  DOI：

  10.1021/ol302627u

文献信息

• Organocatalytic Enantioselective Conjugate Addition of Malonic Acid Half Thioesters to Coumarin-3-carboxylic Acids Using<i>N</i>-Heteroarenesulfonyl<i>Cinchona</i>Alkaloid Amides
  作者：Shuichi Nakamura、Ayaka Toda、Masahide Sano、Tsubasa Hatanaka、Yasuhiro Funahashi

  DOI：10.1002/adsc.201600040

  日期：2016.3.31

  disclose herein an efficient enantioselective conjugate addition reaction between coumarin‐3‐carboxylic acids and malonic acid half thioesters (MAHTs). The reaction was catalyzed by N‐heteroarenesulfonyl Cinchona alkaloid amides to afford double‐decarboxylative conjugate addition products in good yield with high enantioselectivity. The reaction of various coumarin‐3‐carboxylic acids with MAHTs gave products

  我们在本文中公开了香豆素-3-羧酸与丙二酸半硫酯（MAHT）之间的有效对映选择性共轭加成反应。N-杂芳烃磺酰基金鸡纳生物碱酰胺催化该反应，以高收率和高对映选择性提供双脱羧共轭加成产物。各种香豆素-3-羧酸与MAHT的反应可高收率和高对映选择性地产生产物。