1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-3,4-dihydroxy-1,2,3,4,5,6,7,8-octahydronaphthalene | 143121-43-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-3,4-dihydroxy-1,2,3,4,5,6,7,8-octahydronaphthalene
• CAS: 143121-43-1
• 化学式: C₃₄H₄₈O₅Si
• 分子量: 564.838
• InChiKey: LVKKETAGOSKKHE-CDACFMRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-3,4-dihydroxy-1,2,3,4,5,6,7,8-octahydronaphthalene 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以95%的产率得到[(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 2,2-dimethylpropanoate
  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：

  ((1R,2R)-2-Hydroxymethyl-1-methyl-1,2,5,6,7,8-hexahydro-naphthalen-1-yl)-methanol 在 四氧化锇 吡啶 、 咪唑 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 64.25h， 生成 1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-3,4-dihydroxy-1,2,3,4,5,6,7,8-octahydronaphthalene
  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