(2α,4aβ,8β,8aα)-(+/-)-1-(decahydro-8-hydroxy-4a,8-dimethyl-2-naphthalenyl)ethanone | 136734-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2α,4aβ,8β,8aα)-(+/-)-1-(decahydro-8-hydroxy-4a,8-dimethyl-2-naphthalenyl)ethanone
• CAS: 136734-32-2
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: WUXBKEFKDNZEEO-ZOBORPQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (4aα,8α,8aβ)-(+/-)-octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenone 在 氢氧化钾 、 sodium hydroxide 、 重铬酸吡啶 、 硼烷四氢呋喃络合物 、 双氧水 作用下， 以 二甲基亚砜 为溶剂， 反应 114.0h， 生成 (2α,4aβ,8β,8aα)-(+/-)-1-(decahydro-8-hydroxy-4a,8-dimethyl-2-naphthalenyl)ethanone
  参考文献：
  名称：

  Synthesis of all stereoisomers of eudesm-11-en-4-ol. 2. Total synthesis of selin-11-en-4.alpha.-ol, intermedeol, neointermedeol, and paradisiol. First total synthesis of amiteol

  摘要：

  The syntheses of (+/-)-selin-11-en-4-alpha-ol (5), (+/-)-intermedeol (6), (+/-)-neointermedeol (7), (+/-)-amiteol (9), and the four remaining unnatural stereoisomers (+/-)-paradisiol (8), (+/-)-7-epi-amiteol (10), (+/-)-5-epi-neointermedeol (11), and (+/-)-5-epi-paradisiol (12) are described. In addition, the related (+/-)-evuncifer ether (25) has been prepared. The syntheses started from the octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenones 1-4. The reaction sequence employed for the synthesis of 5, 7, 9, and 12 involved Wittig reaction, oxidative hydroboration, oxidation, equilibration, and olefination. For the synthesis of 6, 8, 10, and 11 the interim equilibration step was omitted. The oxidative hydroboration was the key step in these syntheses.

  DOI：

  10.1021/jo00026a012

文献信息

• Synthesis of all stereoisomers of eudesm-11-en-4-ol. 2. Total synthesis of selin-11-en-4.alpha.-ol, intermedeol, neointermedeol, and paradisiol. First total synthesis of amiteol
  作者：Ronald P. W. Kesselmans、Joannes B. P. A. Wijnberg、Adriaan J. Minnaard、Robert E. Walinga、Aede De Groot

  DOI：10.1021/jo00026a012

  日期：1991.12

  The syntheses of (+/-)-selin-11-en-4-alpha-ol (5), (+/-)-intermedeol (6), (+/-)-neointermedeol (7), (+/-)-amiteol (9), and the four remaining unnatural stereoisomers (+/-)-paradisiol (8), (+/-)-7-epi-amiteol (10), (+/-)-5-epi-neointermedeol (11), and (+/-)-5-epi-paradisiol (12) are described. In addition, the related (+/-)-evuncifer ether (25) has been prepared. The syntheses started from the octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenones 1-4. The reaction sequence employed for the synthesis of 5, 7, 9, and 12 involved Wittig reaction, oxidative hydroboration, oxidation, equilibration, and olefination. For the synthesis of 6, 8, 10, and 11 the interim equilibration step was omitted. The oxidative hydroboration was the key step in these syntheses.