(S)-7-(3-hydroxybutoxy)-2H-1-benzopyran-2-one | 209400-07-7

• 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-(3-hydroxybutoxy)-2H-1-benzopyran-2-one
• 英文别名: 7-[(3S)-3-hydroxybutoxy]chromen-2-one
• CAS: 209400-07-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: RLYAABZSQAJJTG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-7-(3-hydroxybutoxy)-2H-1-benzopyran-2-one 在 苯磺酰胺 、 borate buffer 、 horse liver dehydrogenase 、 nicotinamide adenine dinucleotide 作用下， 生成 7-羟基香豆素
  参考文献：
  名称：

  Enantioselective Fluorogenic Assay of Acetate Hydrolysis for Detecting Lipase Catalytic Antibodies

  摘要：

  An enantioselective fluorogenic assay for the kinetic resolution of chiral alkyl acetates is demonstrated with 7-(3-aceroxybutoxy)-2H-1-henzopyran-2-ones (R)- and (S)-4 or 7-(3-acetoxy-2-methylpropoxy)-2H-1-benzopyran-2-ones (R)-4 and (S)-6. The alcohols released by hydrolysis of these acetates are oxidized by horse-liver alcohol dehydrogenase to unstable beta-(aryloxy)carbonyl compounds: which undergo beta-elimination of the strongly fluorescent product umbelliferone (= 7-hydroxy-2H-1-benzopyran-2-one; 3) (lambda(em) = 460 +/- 20 nm, lambda(ex) = 360 +/- 20 nm). Enantioselectivities are calculated from the reaction rates for each enantiomeric acetate. For a series of representative lipases, the reactivities and enantioselectivities under preparative conditions are predicted accurately. This highly sensitive enantioselective assay detects as little as 10 mu g/ml of hydrolytic enzyme, can be carried out in 96-well microtiter plates. and is compatible with cell-cult Ire media. It is, therefore, suited for screening libraries of antibodies for enantioselective lipase catalytic antibodies.

  DOI：

  10.1002/(sici)1522-2675(19990310)82:3<400::aid-hlca400>3.0.co;2-c
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (S)-7-(3-hydroxybutoxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Enantioselective Fluorogenic Assay of Acetate Hydrolysis for Detecting Lipase Catalytic Antibodies

  摘要：

  An enantioselective fluorogenic assay for the kinetic resolution of chiral alkyl acetates is demonstrated with 7-(3-aceroxybutoxy)-2H-1-henzopyran-2-ones (R)- and (S)-4 or 7-(3-acetoxy-2-methylpropoxy)-2H-1-benzopyran-2-ones (R)-4 and (S)-6. The alcohols released by hydrolysis of these acetates are oxidized by horse-liver alcohol dehydrogenase to unstable beta-(aryloxy)carbonyl compounds: which undergo beta-elimination of the strongly fluorescent product umbelliferone (= 7-hydroxy-2H-1-benzopyran-2-one; 3) (lambda(em) = 460 +/- 20 nm, lambda(ex) = 360 +/- 20 nm). Enantioselectivities are calculated from the reaction rates for each enantiomeric acetate. For a series of representative lipases, the reactivities and enantioselectivities under preparative conditions are predicted accurately. This highly sensitive enantioselective assay detects as little as 10 mu g/ml of hydrolytic enzyme, can be carried out in 96-well microtiter plates. and is compatible with cell-cult Ire media. It is, therefore, suited for screening libraries of antibodies for enantioselective lipase catalytic antibodies.

  DOI：

  10.1002/(sici)1522-2675(19990310)82:3<400::aid-hlca400>3.0.co;2-c