1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-1,2,5,6,7,8-hexahydronaphthalene | 143121-42-0

• 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>-1,2,5,6,7,8-hexahydronaphthalene
• CAS: 143121-42-0
• 化学式: C₃₄H₄₆O₃Si
• 分子量: 530.823
• InChiKey: IZOJQFMULLVDED-NDOVKIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-1,2,5,6,7,8-hexahydronaphthalene 在 四氧化锇 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 以64%的产率得到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
• 作为产物：
  描述：

  ((1R,2R)-2-Hydroxymethyl-1-methyl-1,2,5,6,7,8-hexahydro-naphthalen-1-yl)-methanol 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 1-<<(diphenyl-tert-butylsilyl)oxy>methyl>-1-methyl-2-<(pivaloyloxy)methyl>-1,2,5,6,7,8-hexahydronaphthalene
  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