(1S,6S)-2,2-dimethyl-1-(2'-methoxycarbonyl-3'-oxobutyl)-6-methoxymethyloxycyclohexane | 924884-78-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (1S,6S)-2,2-dimethyl-1-(2'-methoxycarbonyl-3'-oxobutyl)-6-methoxymethyloxycyclohexane
• 英文别名: methyl 2-[[(1S,6S)-6-(methoxymethoxy)-2,2-dimethylcyclohexyl]methyl]-3-oxobutanoate
• CAS: 924884-78-6
• 化学式: C₁₆H₂₈O₅
• 分子量: 300.395
• InChiKey: GRFXBPJQVMATPR-IUZLNWEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,6S)-2,2-dimethyl-1-(2'-methoxycarbonyl-3'-oxobutyl)-6-methoxymethyloxycyclohexane 在 sodium hydroxide 、 sodium tetrahydroborate 、 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 12.0h， 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 咪唑 、 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 21.5h， 生成 (1S,6S)-2,2-dimethyl-1-(2'-methoxycarbonyl-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

文献信息

• New total synthesis of (+)-ambrein
  作者：Naoko Fujiwara、Masako Kinoshita、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2006.11.015

  日期：2006.11

  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.