(5,6,7,8-Tetrahydro-4-methyl-1-naphthalenyl)-1-ethanone | 13577-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (5,6,7,8-Tetrahydro-4-methyl-1-naphthalenyl)-1-ethanone
• 英文别名: 1-(4-Methyl-5,6,7,8-tetrahydronaphthalen-1-yl)ethanone
• CAS: 13577-42-9
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: WUXYPEYNVPBBPK-UHFFFAOYSA-N

物化性质

• 沸点：
  329.8±31.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (7Z)-7-[isocyano-(4-methylphenyl)sulfonylmethylidene]-4a-methyl-1,2,3,4,5,6-hexahydronaphthalene 、 碘甲烷 生成 (5,6,7,8-Tetrahydro-4-methyl-1-naphthalenyl)-1-ethanone 、 (+/-)-(4,4a,5,6,7,8-Hexahydro-4a-methyl-2-naphthalenyl)-1-ethanone
  参考文献：
  名称：

  Regioselective intramolecular base-Induced synthesis of .alpha.,.beta.-Unsaturated. Acyldecalins from Decalones via Carbon Homologation with isocyanomethyl Tosylate (TosMIC). Synthesis of (.+-.)-6-Eudesmen-4.alpha.-ol and (.+-.)-Vetiselinene

  摘要：

  Reaction of decalones 6a-e with TosMIC gives adducts 7a-e which can be methylated concomitant with regioselective migration of the double bond to an endocyclic position. The regioselectivity of the double bond migration is determined by the presence or absence of a free hydroxyl group at C(4). Base-catalyzed methylation of TosMIC adducts 7b-d, possessing a free hydroxyl group at C(4), and subsequent acid-catalyzed hydrolysis led preferentially to the C(6)-C(7) double bond isomers 10b-d, respectively. An intramolecular deprotonation of H-6 is considered to be responsible for this regioselectivity. If the hydroxyl group at C(4) is absent or protected as in 7a and 7e, respectively, the C(7)-C(8) double bond isomers 9a and 9c are obtained via an intermolecular abstraction of a sterically less shielded proton at C(8). The usefulness of this methodology is illustrated by the total synthesis of (+/-)-6-eudesmen-4 alpha-ol (18) and (+/-)-vetiselinene (22).

  DOI：

  10.1021/jo00112a044