(+/-)-(1R,5S,7r)-7-(3-benzyloxy-3-oxido-2,4-dioxa-3-phospha-bicyclo[3.3.0]octyl)-2H-1-benzopyran-2-one | 474087-23-5

• 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: (+/-)-(1R,5S,7r)-7-(3-benzyloxy-3-oxido-2,4-dioxa-3-phospha-bicyclo[3.3.0]octyl)-2H-1-benzopyran-2-one
• CAS: 474087-23-5
• 化学式: C₂₁H₁₉O₇P
• 分子量: 414.351
• InChiKey: JZIFCLMCYWJYLG-PGOVJWPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.2
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R,5S,7r)-7-(3-benzyloxy-3-oxido-2,4-dioxa-3-phospha-bicyclo[3.3.0]octyl)-2H-1-benzopyran-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、98.07 kPa 条件下， 反应 3.0h， 以67%的产率得到(+/-)-(1r,3R,4S)-7-(3-phosphonoxy-4-hydroxycyclopentyloxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Enzyme Fingerprints of Activity, and Stereo- and Enantioselectivity from Fluorogenic and Chromogenic Substrate Arrays

  摘要：

  A series of stereochemically and structurally diverse fluorogenic and chromogenic substrates for hydrolytic enzymes has been synthesized and used to characterize enzyme activity profiles of esterases, lipases, proteases, peptidases, phosphatases, and epoxide hydrolases. The substrates used are particularly resilient to nonspecific reactions due to their mechanism of activation. The activities recorded with the individual substrates are therefore remarkably reproducible, and enable us to use the overall pattern of activity as a specific fingerprint for the enzyme sample. Fingerprints of activity, and enantio- and stereoselectivity are displayed as arrays of color-scale squares that are easily analyzed visually. Such fingerprints might be useful for quality control, enzyme discovery, and possibly for addressing the issue of functional convergence in enzymes.

  DOI：

  10.1002/1521-3765(20020715)8:14<3211::aid-chem3211>3.0.co;2-g
• 作为产物：
  描述：

  3-环戊烯-1-醇 在 吡啶 、 四氮唑 、 AD-mix-α 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 54.75h， 生成 (+/-)-(1R,5S,7r)-7-(3-benzyloxy-3-oxido-2,4-dioxa-3-phospha-bicyclo[3.3.0]octyl)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Enzyme Fingerprints of Activity, and Stereo- and Enantioselectivity from Fluorogenic and Chromogenic Substrate Arrays

  摘要：

  A series of stereochemically and structurally diverse fluorogenic and chromogenic substrates for hydrolytic enzymes has been synthesized and used to characterize enzyme activity profiles of esterases, lipases, proteases, peptidases, phosphatases, and epoxide hydrolases. The substrates used are particularly resilient to nonspecific reactions due to their mechanism of activation. The activities recorded with the individual substrates are therefore remarkably reproducible, and enable us to use the overall pattern of activity as a specific fingerprint for the enzyme sample. Fingerprints of activity, and enantio- and stereoselectivity are displayed as arrays of color-scale squares that are easily analyzed visually. Such fingerprints might be useful for quality control, enzyme discovery, and possibly for addressing the issue of functional convergence in enzymes.

  DOI：

  10.1002/1521-3765(20020715)8:14<3211::aid-chem3211>3.0.co;2-g