(1R,6S)-(+)-2,2-dimethyl-1-hydroxymethyl-6-methoxymethyloxycyclohexane | 924884-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,6S)-(+)-2,2-dimethyl-1-hydroxymethyl-6-methoxymethyloxycyclohexane
• 英文别名: [(1R,6S)-6-(methoxymethoxy)-2,2-dimethylcyclohexyl]methanol
• CAS: 924884-76-4
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: XHCNZMOIGBOQJS-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,6S)-(+)-2,2-dimethyl-1-hydroxymethyl-6-methoxymethyloxycyclohexane 在 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 碘 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 32.0h， 生成 (1S,6S)-(+)-2,2-dimethyl-1-[3'-(benzothiazole-2''-sulfanyl)butyl]-6-methoxymethyloxycyclohexane
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015
• 作为产物：
  描述：

  (1S,6S)-(-)-2,2-dimethyl-1-methoxycarbonyl-6-methoxymethyloxycyclohexane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以97%的产率得到(1R,6S)-(+)-2,2-dimethyl-1-hydroxymethyl-6-methoxymethyloxycyclohexane
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015