(3R,3aS,7R,7aS)-3-Hydroxymethyl-3a,7,7a-trimethyl-octahydro-inden-5-ol | 342794-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,3aS,7R,7aS)-3-Hydroxymethyl-3a,7,7a-trimethyl-octahydro-inden-5-ol
• 英文别名: (3R,3aS,7R,7aS)-3-(hydroxymethyl)-3a,7,7a-trimethyl-2,3,4,5,6,7-hexahydro-1H-inden-5-ol
• CAS: 342794-75-6
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: JQZHMURPMPEUIZ-ATQWOEOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,3aS,7R,7aS)-3-Hydroxymethyl-3a,7,7a-trimethyl-octahydro-inden-5-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (3R,3aS,7R,7aS)-3,3a,7,7a-Tetramethyl-octahydro-inden-5-ol
  参考文献：
  名称：

  Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone

  摘要：

  A homochiral bicyclic ketone having a pinguisane skeleton has: been synthesised starting from homochiral methyl 3-[(1 'S,6 'R)-1 ' ,6 ' -dimethyl-2 ' -oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi-Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00041-6
• 作为产物：
  描述：

  (1R,3aS,4R,7aS)-3a,4,7a-Trimethyl-6-oxo-octahydro-indene-1-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以79%的产率得到(3R,3aS,7R,7aS)-3-Hydroxymethyl-3a,7,7a-trimethyl-octahydro-inden-5-ol
  参考文献：
  名称：

  Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone

  摘要：

  A homochiral bicyclic ketone having a pinguisane skeleton has: been synthesised starting from homochiral methyl 3-[(1 'S,6 'R)-1 ' ,6 ' -dimethyl-2 ' -oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi-Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00041-6