(1S,7aS)-1-(methoxymethoxymethyl)-7a-methyl-3,5,6,7-tetrahydro-2H-indene-1,5,6-triol | 959470-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,7aS)-1-(methoxymethoxymethyl)-7a-methyl-3,5,6,7-tetrahydro-2H-indene-1,5,6-triol
• CAS: 959470-18-9
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: ATCCTUMHOMFJDE-IFWUJCSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,7aS)-1-(methoxymethoxymethyl)-7a-methyl-3,5,6,7-tetrahydro-2H-indene-1,5,6-triol 、 三氟甲磺酸三甲基硅酯 在 2,3,5-三甲基吡啶 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以75%的产率得到
  参考文献：
  名称：

  A Domino-Based Approach toward Stereodefined Heavily Functionalized Cyclohexanes:  Synthesis of Iridal's Core Structure

  摘要：

  A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.

  DOI：

  10.1021/ol702056s
• 作为产物：
  描述：

  (1S,7aS)-1-((methoxymethoxy)methyl)-7a-methyl-5,6-bis((trimethylsilyl)oxy)-2,3,5,6,7,7a-hexahydro-1H-inden-1-ol 在 四丁基氟化铵 作用下， 生成 (1S,7aS)-1-(methoxymethoxymethyl)-7a-methyl-3,5,6,7-tetrahydro-2H-indene-1,5,6-triol
  参考文献：
  名称：

  A Domino-Based Approach toward Stereodefined Heavily Functionalized Cyclohexanes:  Synthesis of Iridal's Core Structure

  摘要：

  A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.

  DOI：

  10.1021/ol702056s