(S)-7-(2-methyl-3-oxoprop-1-yloxy)-2H-benzopyran-2-one | 325855-85-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (S)-7-(2-methyl-3-oxoprop-1-yloxy)-2H-benzopyran-2-one
• CAS: 325855-85-4
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: VUIBVLPWOYGDCA-SECBINFHSA-N

物化性质

• 沸点：
  422.2±45.0 °C(predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  56.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(三甲基硅氧基)丙烯 、 (S)-7-(2-methyl-3-oxoprop-1-yloxy)-2H-benzopyran-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-7-(3-hydroxy-2-methyl-5-oxohex-1-yloxy)-2H-benzopyran-2-one 、 (2S,3S)-7-(3-hydroxy-2-methyl-5-oxohex-1-yloxy)-2H-benzopyran-2-one
  参考文献：
  名称：

  Fluorogenic Polypropionate Fragments for Detecting Stereoselective Aldolases

  摘要：

  A series of fluorogenic polypropionate fragments has been prepared. These undergo retroaldolization to an intermediate aldehyde that liberates the fluorescent product umbelliferone by a secondary beta-elimination reaction. leading to a >20-fold increase in fluorescence (lambda(em) = 460 +/- 20 nm, lambdaex = 360 +/- 20 nm). By applying the principle of microscopic reversibility to the reversible aldol reaction, we can use these substrates to detect stereoselective aldolases. Test substrates are available to probe the classical cases of syn- and anti-selective aldolization (11a-d), Cram/ anti-Cram-selective aldolization (10a-d), and double stereoselective aldolization (3a-h). The selectivity of aldolase antibody 38C2 for these substrates is demonstrated as an example. The assay is suitable for high-throughput screening for catalysis in microtiter plates, and therefore provides a convenient tool for the isolation of new stereoselective aldolases from catalyst libraries.

  DOI：

  10.1002/1521-3765(20001117)6:22<4154::aid-chem4154>3.0.co;2-g
• 作为产物：
  描述：

  (R)-7-(3-hydroxy-2-methylpropoxy)-2H-1-benzopyran-2-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以70%的产率得到(S)-7-(2-methyl-3-oxoprop-1-yloxy)-2H-benzopyran-2-one
  参考文献：
  名称：

  Fluorogenic Polypropionate Fragments for Detecting Stereoselective Aldolases

  摘要：

  A series of fluorogenic polypropionate fragments has been prepared. These undergo retroaldolization to an intermediate aldehyde that liberates the fluorescent product umbelliferone by a secondary beta-elimination reaction. leading to a >20-fold increase in fluorescence (lambda(em) = 460 +/- 20 nm, lambdaex = 360 +/- 20 nm). By applying the principle of microscopic reversibility to the reversible aldol reaction, we can use these substrates to detect stereoselective aldolases. Test substrates are available to probe the classical cases of syn- and anti-selective aldolization (11a-d), Cram/ anti-Cram-selective aldolization (10a-d), and double stereoselective aldolization (3a-h). The selectivity of aldolase antibody 38C2 for these substrates is demonstrated as an example. The assay is suitable for high-throughput screening for catalysis in microtiter plates, and therefore provides a convenient tool for the isolation of new stereoselective aldolases from catalyst libraries.

  DOI：

  10.1002/1521-3765(20001117)6:22<4154::aid-chem4154>3.0.co;2-g