(7S,8S,8aS)-8-hydroxy-7-methyl-7-phenylmethoxy-3-[(E)-prop-1-enyl]-8,8a-dihydro-1H-isochromen-6-one | 1395877-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂非酮类
• 英文名称: (7S,8S,8aS)-8-hydroxy-7-methyl-7-phenylmethoxy-3-[(E)-prop-1-enyl]-8,8a-dihydro-1H-isochromen-6-one
• CAS: 1395877-90-3
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: LGCFWWGZMYXFPA-ZWOYOGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (7S,8S,8aS)-8-hydroxy-7-methyl-7-phenylmethoxy-3-[(E)-prop-1-enyl]-8,8a-dihydro-1H-isochromen-6-one 在 4-二甲氨基吡啶 、 三氯化硼 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 sch 725680
  参考文献：
  名称：

  Total Synthesis of (+)-Sch 725680: Inhibitor of Mammalian A–, B–, and Y–Family DNA Polymerases

  摘要：

  The total synthesis of (+)-Sch 725680, a member of the hydrogenated azaphilone family, has been accomplished. The synthesis confirmed the absolute configuration and biological activities of the natural product. A key reaction to construct a hydrogenated azaphilone core skeleton is a Ti-mediated aldol reaction.

  DOI：

  10.1021/ol301865u
• 作为产物：
  描述：

  在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以78%的产率得到(7S,8S,8aS)-8-hydroxy-7-methyl-7-phenylmethoxy-3-[(E)-prop-1-enyl]-8,8a-dihydro-1H-isochromen-6-one
  参考文献：
  名称：

  Total Synthesis of (+)-Sch 725680: Inhibitor of Mammalian A–, B–, and Y–Family DNA Polymerases

  摘要：

  The total synthesis of (+)-Sch 725680, a member of the hydrogenated azaphilone family, has been accomplished. The synthesis confirmed the absolute configuration and biological activities of the natural product. A key reaction to construct a hydrogenated azaphilone core skeleton is a Ti-mediated aldol reaction.

  DOI：

  10.1021/ol301865u

文献信息

• Total Synthesis of (+)-Sch 725680: Inhibitor of Mammalian A–, B–, and Y–Family DNA Polymerases
  作者：Toshifumi Takeuchi、Yoshiyuki Mizushina、Satoshi Takaichi、Natsuki Inoue、Kouji Kuramochi、Satomi Shimura、Yusuke Myobatake、Yuri Katayama、Kenji Takemoto、Shogo Endo、Shinji Kamisuki、Fumio Sugawara

  DOI：10.1021/ol301865u

  日期：2012.9.7

  The total synthesis of (+)-Sch 725680, a member of the hydrogenated azaphilone family, has been accomplished. The synthesis confirmed the absolute configuration and biological activities of the natural product. A key reaction to construct a hydrogenated azaphilone core skeleton is a Ti-mediated aldol reaction.