(1'R,3'aR,4'aR,8'aR,9'S,9'aS)-1'-methyl-9'-[(E)-2-[5-tri(propan-2-yl)silyloxypyridin-2-yl]ethenyl]spiro[1,3-dioxolane-2,6'-1,3a,4,4a,5,7,8,8a,9,9a-decahydrobenzo[f][2]benzofuran]-3'-one | 618386-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1'R,3'aR,4'aR,8'aR,9'S,9'aS)-1'-methyl-9'-[(E)-2-[5-tri(propan-2-yl)silyloxypyridin-2-yl]ethenyl]spiro[1,3-dioxolane-2,6'-1,3a,4,4a,5,7,8,8a,9,9a-decahydrobenzo[f][2]benzofuran]-3'-one
• CAS: 618386-07-5
• 化学式: C₃₁H₄₇NO₅Si
• 分子量: 541.803
• InChiKey: URCRJKJVMZNBSI-QMLCAOFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'R,3'aR,4'aR,8'aR,9'S,9'aS)-1'-methyl-9'-[(E)-2-[5-tri(propan-2-yl)silyloxypyridin-2-yl]ethenyl]spiro[1,3-dioxolane-2,6'-1,3a,4,4a,5,7,8,8a,9,9a-decahydrobenzo[f][2]benzofuran]-3'-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以100%的产率得到(1'R,3'aR,4'aR,8'aR,9'S,9'aS)-9'-[(E)-2-(5-hydroxypyridin-2-yl)ethenyl]-1'-methylspiro[1,3-dioxolane-2,6'-1,3a,4,4a,5,7,8,8a,9,9a-decahydrobenzo[f][2]benzofuran]-3'-one
  参考文献：
  名称：

  Discovery of a Novel, Orally Active Himbacine-Based Thrombin Receptor Antagonist (SCH 530348) with Potent Antiplatelet Activity

  摘要：

  The discovery of an exceptionally potent series of thrombin receptor (PAR-1) antagonists based on the natural product himbacine is described. Optimization of this series has led to the discovery of 4 (SCH 530348), a potent, oral antiplatelet agent that is currently undergoing Phase-III clinical trials for acute coronary syndrome (unstable angina/non-ST segment elevation myocardial infarction) and secondary prevention of cardiovascular events in high-risk patients.

  DOI：

  10.1021/jm800180e
• 作为产物：
  描述：

  硫酸沃拉帕沙中间体 、 (1'R,3'aR,4'aR,8'aR,9'S,9'aS)-9'-acetyl-1'-methylspiro[1,3-dioxolane-2,6'-1,3a,4,4a,5,7,8,8a,9,9a-decahydrobenzo[f][2]benzofuran]-3'-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 (1'R,3'aR,4'aR,8'aR,9'S,9'aS)-1'-methyl-9'-[(E)-2-[5-tri(propan-2-yl)silyloxypyridin-2-yl]ethenyl]spiro[1,3-dioxolane-2,6'-1,3a,4,4a,5,7,8,8a,9,9a-decahydrobenzo[f][2]benzofuran]-3'-one
  参考文献：
  名称：

  Discovery of a Novel, Orally Active Himbacine-Based Thrombin Receptor Antagonist (SCH 530348) with Potent Antiplatelet Activity

  摘要：

  The discovery of an exceptionally potent series of thrombin receptor (PAR-1) antagonists based on the natural product himbacine is described. Optimization of this series has led to the discovery of 4 (SCH 530348), a potent, oral antiplatelet agent that is currently undergoing Phase-III clinical trials for acute coronary syndrome (unstable angina/non-ST segment elevation myocardial infarction) and secondary prevention of cardiovascular events in high-risk patients.

  DOI：

  10.1021/jm800180e