<7R-<1α,4aα,7α(S*),8aα>>-decahydro-1-hydroxy-1,4a-dimethyl-7-(1-methyl-2-iodoethyl)naphthalene | 136631-18-0

• 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: <7R-<1α,4aα,7α(S*),8aα>>-decahydro-1-hydroxy-1,4a-dimethyl-7-(1-methyl-2-iodoethyl)naphthalene
• 英文别名: (1S,4aR,7R,8aS)-7-[(2S)-1-iodopropan-2-yl]-1,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-ol
• CAS: 136631-18-0
• 化学式: C₁₅H₂₇IO
• 分子量: 350.283
• InChiKey: YNTIFAAEXNWDEI-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <7R-<1α,4aα,7α(S*),8aα>>-decahydro-1-hydroxy-1,4a-dimethyl-7-(1-methyl-2-iodoethyl)naphthalene 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 9.0h， 以98%的产率得到(+)-5-epi-neointermedeol
  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
• 作为产物：
  描述：

  methyl (2S)-2-[(3aS,6R,7aS)-3a,7b-dimethyl-1a,2,3,4,5,6,7,7a-octahydronaphtho[1,2-b]oxiren-6-yl]propanoate 在 吡啶 、 lithium aluminium tetrahydride 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 68.67h， 生成 <7R-<1α,4aα,7α(S*),8aα>>-decahydro-1-hydroxy-1,4a-dimethyl-7-(1-methyl-2-iodoethyl)naphthalene
  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