(2R,6S,7R,12S)-4,4,12-trimethyl-3,5,10-trioxatetracyclo[11.4.0.02,6.07,12]heptadec-1(13)-en-9-one | 143121-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (2R,6S,7R,12S)-4,4,12-trimethyl-3,5,10-trioxatetracyclo[11.4.0.02,6.07,12]heptadec-1(13)-en-9-one
• CAS: 143121-50-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: OCFUQZDUKBMIME-PWXKEOIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6S,7R,12S)-4,4,12-trimethyl-3,5,10-trioxatetracyclo[11.4.0.02,6.07,12]heptadec-1(13)-en-9-one 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以93%的产率得到(4aS,5R,6S,10bR)-5,6-dihydroxy-10b-methyl-4,4a,5,6,7,8,9,10-octahydro-1H-benzo[h]isochromen-3-one
  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：

  [(3aS,4S,5S,9bR)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2,5-trimethyl-4,6,7,8,9,9b-hexahydro-3aH-benzo[e][1,3]benzodioxol-4-yl]methyl methanesulfonate 在 重铬酸吡啶 、 molecular sieve 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 37.0h， 生成 (2R,6S,7R,12S)-4,4,12-trimethyl-3,5,10-trioxatetracyclo[11.4.0.02,6.07,12]heptadec-1(13)-en-9-one
  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

文献信息

• Synthetic studies on wortmannin and 11-desacetoxywortmannin
  作者：Chris A. Broka、Beatrice Ruhland

  DOI：10.1021/jo00044a025

  日期：1992.8

  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.