((1R,2S)-2-Hydroxymethyl-2-methyl-1,2,5,6,7,8-hexahydro-naphthalen-1-yl)-methanol | 143121-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2S)-2-Hydroxymethyl-2-methyl-1,2,5,6,7,8-hexahydro-naphthalen-1-yl)-methanol
• 英文别名: [(1R,2S)-2-(hydroxymethyl)-2-methyl-5,6,7,8-tetrahydro-1H-naphthalen-1-yl]methanol
• CAS: 143121-41-9
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: UEPPWMVWUQTYTC-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  柠康酸酐 、 5,6,7,8-tetrahydrocoumarin 在 红铝 作用下， 生成 ((1R,2R)-2-Hydroxymethyl-1-methyl-1,2,5,6,7,8-hexahydro-naphthalen-1-yl)-methanol 、 ((1R,2S)-2-Hydroxymethyl-2-methyl-1,2,5,6,7,8-hexahydro-naphthalen-1-yl)-methanol
  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.