1-[1-Dimethylamino-meth-(Z)-ylidene]-10-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-3-oxa-phenanthrene-2,9-dione | 143121-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-[1-Dimethylamino-meth-(Z)-ylidene]-10-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-3-oxa-phenanthrene-2,9-dione
• CAS: 143121-54-4
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: RUKMBTAOHIFMQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[1-Dimethylamino-meth-(Z)-ylidene]-10-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-3-oxa-phenanthrene-2,9-dione 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 10b-Methyl-1,7,8,9,10,10b-hexahydro-2,5-dioxa-acephenanthrylene-3,6-dione
  参考文献：
  名称：

  Synthetic studies on wortmannin and 11-desacetoxywortmannin

  摘要：

  This report describes the first synthesis of the highly reactive furanocyclohexadienone lactone subunit of the natural products wortmannin (1) and 11-desacetoxywortmannin (2). The simplified wortmannin analogue 6 was prepared by acid treatment of aminomethylene lactone 22 in analogy to the known conversion of lactone 3 into wortmannin. Compound 22 was, in turn, prepared from the readily accessible lactone 18 through sequential oxidations and introduction of the aminomethylene unit using tris(dimethylamino)methane.

  DOI：

  10.1021/jo00044a025
• 作为产物：
  描述：

  在 水 、 copper diacetate 作用下， 生成 1-[1-Dimethylamino-meth-(Z)-ylidene]-10-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-3-oxa-phenanthrene-2,9-dione
  参考文献：
  名称：

  Synthetic studies on wortmannin and 11-desacetoxywortmannin

  摘要：

  This report describes the first synthesis of the highly reactive furanocyclohexadienone lactone subunit of the natural products wortmannin (1) and 11-desacetoxywortmannin (2). The simplified wortmannin analogue 6 was prepared by acid treatment of aminomethylene lactone 22 in analogy to the known conversion of lactone 3 into wortmannin. Compound 22 was, in turn, prepared from the readily accessible lactone 18 through sequential oxidations and introduction of the aminomethylene unit using tris(dimethylamino)methane.

  DOI：

  10.1021/jo00044a025