((R)-2-2,3-Dihydro-benzofuran-2-yl-2-oxo-ethyl)-phosphonic acid dimethyl ester | 66598-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: ((R)-2-2,3-Dihydro-benzofuran-2-yl-2-oxo-ethyl)-phosphonic acid dimethyl ester
• CAS: 66598-85-4
• 化学式: C₁₂H₁₅O₅P
• 分子量: 270.222
• InChiKey: DQYZFHZDPCAZEZ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((R)-2-2,3-Dihydro-benzofuran-2-yl-2-oxo-ethyl)-phosphonic acid dimethyl ester 在 正丁基锂 、 zinc borohydride 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.42h， 生成 (3aR,4R,5R,6aS)-4-[(E)-(R)-3-(R)-2,3-Dihydro-benzofuran-2-yl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol
  参考文献：
  名称：

  Structure-activity studies of configurationally rigid arylprostaglandins

  摘要：

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.

  DOI：

  10.1021/jm00357a004
• 作为产物：
  描述：

  苯并二氢呋喃-2-羧酸 在 正丁基锂 、 硫酸 作用下， 反应 1.08h， 生成 ((R)-2-2,3-Dihydro-benzofuran-2-yl-2-oxo-ethyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Structure-activity studies of configurationally rigid arylprostaglandins

  摘要：

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.

  DOI：

  10.1021/jm00357a004