(1S,6S)-(+)-2,2-dimethyl-1-(3'-oxobutyl)-6-methoxymethyloxycyclohexane | 924884-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,6S)-(+)-2,2-dimethyl-1-(3'-oxobutyl)-6-methoxymethyloxycyclohexane
• CAS: 924884-79-7
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: ODOFRCPTKRRYCF-OLZOCXBDSA-N

物化性质

• 沸点：
  302.4±12.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (1S,6S)-(+)-2,2-dimethyl-1-(3'-oxobutyl)-6-methoxymethyloxycyclohexane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以3.686 g的产率得到(1S,6S)-2,2-dimethyl-1-(3'-hydroxybutyl)-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 咪唑 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 碘 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 29.0h， 生成 (1S,6S)-(+)-2,2-dimethyl-1-(3'-oxobutyl)-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