(1'R,1S,2R,3R,6R)-2-(1'-hydroxypropyl)-6-isopropyl-3-methylcyclohexanol | 210291-39-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1'R,1S,2R,3R,6R)-2-(1'-hydroxypropyl)-6-isopropyl-3-methylcyclohexanol
• 英文别名: (1S,2R,3R,6R)-2-[(1R)-1-hydroxypropyl]-3-methyl-6-propan-2-ylcyclohexan-1-ol
• CAS: 210291-39-7
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: XERXDKRPNBNZGU-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  2,2-二甲氧基丙烷 、 (1'R,1S,2R,3R,6R)-2-(1'-hydroxypropyl)-6-isopropyl-3-methylcyclohexanol 在 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以75%的产率得到(4R,4aR,5R,8R,8aS)-4-Ethyl-8-isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine
  参考文献：
  名称：

  Synthesis and proof of stereostructure of a new (+)-isomenthone-derived homochiral 1,3-diol

  摘要：

  Diastereopure (+)-isomenthone-derived ketoalcohol 2 was converted to the homochiral 1,3-diol 6 either by direct reduction or reduction of silyl protected derivatives. The diastereomeric preference of the reduction was the same in all cases. Reduction of 2 with NaBH4 gave essentially a single diastereomer, while reduction with LiAlH4 gave similar to 6:1 selectivity in favour of the same diastereomer. Reduction of the silyl protected substrates 7 and 8 gave, after column chromatography, 98% yield of a single diastereomer, desilylation of which established this to be the same; diastereomer as obtained through hydride reductions of unprotected 2. The structure of diol 6 was proven through coupling data and NOE experiments at 600 MHz. Overall, two stereochemistry introducing steps have elaborated the two stereogenic centres of (+)-isomenthone to the five contiguous stereogenic centres of 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00013-5
• 作为产物：
  描述：

  (1S,2S,3R,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-cyclohexanol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以94%的产率得到(1'R,1S,2R,3R,6R)-2-(1'-hydroxypropyl)-6-isopropyl-3-methylcyclohexanol
  参考文献：
  名称：

  Synthesis and proof of stereostructure of a new (+)-isomenthone-derived homochiral 1,3-diol

  摘要：

  Diastereopure (+)-isomenthone-derived ketoalcohol 2 was converted to the homochiral 1,3-diol 6 either by direct reduction or reduction of silyl protected derivatives. The diastereomeric preference of the reduction was the same in all cases. Reduction of 2 with NaBH4 gave essentially a single diastereomer, while reduction with LiAlH4 gave similar to 6:1 selectivity in favour of the same diastereomer. Reduction of the silyl protected substrates 7 and 8 gave, after column chromatography, 98% yield of a single diastereomer, desilylation of which established this to be the same; diastereomer as obtained through hydride reductions of unprotected 2. The structure of diol 6 was proven through coupling data and NOE experiments at 600 MHz. Overall, two stereochemistry introducing steps have elaborated the two stereogenic centres of (+)-isomenthone to the five contiguous stereogenic centres of 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00013-5