(+/-)-1,3,4,5,6,7-hexahydro-4a(2H)-naphthaleneacetaldehyde | 39832-80-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1,3,4,5,6,7-hexahydro-4a(2H)-naphthaleneacetaldehyde
• 英文别名: Δ⁴⁽¹⁰⁾-9-Octalyl-acetaldehyd；Bicyclo<4.4.0>dec-1(2)-en-6-acetaldehyd；(1,3,4,5,6,7-hexahydro-2H-[4a]naphthyl)-acetaldehyde；1,3,4,5,6,7-hexahydro-4a(2H)-naphthalenylacetaldehyde；2-(2,3,4,5,6,7-hexahydro-1H-naphthalen-4a-yl)acetaldehyde
• CAS: 39832-80-9
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: YDRJWGVVWNOZCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-1,3,4,5,6,7-hexahydro-4a(2H)-naphthaleneacetaldehyde 在 lithium aluminium tetrahydride 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (+/-)-4a-(2-bromoethyl)-1,2,3,4,4a,5,6,7-octanaphthalene
  参考文献：
  名称：

  Cyclopentannulation by an Iterative Process of Sequential Claisen Rearrangement and Enyne Radical Closure:  Routes to Triquinane and Propellane Systems and Use in the Synthesis of (±)-Ceratopicanol

  摘要：

  Cycloalkenyl acetylenes 4, which are easily prepared from allylic alcohols by Claisen rearrangement and homologation (1 --> 4), generally undergo radical cyclization (4 --> 6) on treatment with stannyl radicals. The products (6) can themselves be converted into allylic alcohols, so that the annulation sequence can then be repeated. In certain cases enyne cyclization initiated by stannyl radicals does not work, but an alternative process (cf. Scheme 9) of epoxide opening with bis(cyclopentadienyl)titanium(III) chloride can then be used. Di- and triquinanes (Scheme 3) were made by the stannyl radical approach; the epoxide route was used to prepare a simple propellane (Scheme 4) and in a synthesis of (+)-ceratopicanol (Schemes 5 and 9).

  DOI：

  10.1021/jo951930h
• 作为产物：
  描述：

  3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 potassium hydride 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 paraffin 、 萘烷 为溶剂， 反应 130.0h， 生成 (+/-)-1,3,4,5,6,7-hexahydro-4a(2H)-naphthaleneacetaldehyde
  参考文献：
  名称：

  Cyclopentannulation by an Iterative Process of Sequential Claisen Rearrangement and Enyne Radical Closure:  Routes to Triquinane and Propellane Systems and Use in the Synthesis of (±)-Ceratopicanol

  摘要：

  Cycloalkenyl acetylenes 4, which are easily prepared from allylic alcohols by Claisen rearrangement and homologation (1 --> 4), generally undergo radical cyclization (4 --> 6) on treatment with stannyl radicals. The products (6) can themselves be converted into allylic alcohols, so that the annulation sequence can then be repeated. In certain cases enyne cyclization initiated by stannyl radicals does not work, but an alternative process (cf. Scheme 9) of epoxide opening with bis(cyclopentadienyl)titanium(III) chloride can then be used. Di- and triquinanes (Scheme 3) were made by the stannyl radical approach; the epoxide route was used to prepare a simple propellane (Scheme 4) and in a synthesis of (+)-ceratopicanol (Schemes 5 and 9).

  DOI：

  10.1021/jo951930h

文献信息

• Stereospecific Angular Alkylation. A New Application of the Claisen Rearrangement¹
  作者：Albert W. Burgstahler、Ivan C. Nordin

  DOI：10.1021/ja01462a039

  日期：1961.1
• STEREOSPECIFIC INTRODUCTION OF ANGULAR SUBSTITUENTS BY THE CLAISEN REARRANGEMENT
  作者：Albert W. Burgstahler、Ivan C. Nordin

  DOI：10.1021/ja01521a064

  日期：1959.6
• Cyclopentannulation by an Iterative Process of Sequential Claisen Rearrangement and Enyne Radical Closure:  Routes to Triquinane and Propellane Systems and Use in the Synthesis of (±)-Ceratopicanol
  作者：D. L. J. Clive、Steven R. Magnuson、Hartford W. Manning、Darrin L. Mayhew

  DOI：10.1021/jo951930h

  日期：1996.1.1

  Cycloalkenyl acetylenes 4, which are easily prepared from allylic alcohols by Claisen rearrangement and homologation (1 --> 4), generally undergo radical cyclization (4 --> 6) on treatment with stannyl radicals. The products (6) can themselves be converted into allylic alcohols, so that the annulation sequence can then be repeated. In certain cases enyne cyclization initiated by stannyl radicals does not work, but an alternative process (cf. Scheme 9) of epoxide opening with bis(cyclopentadienyl)titanium(III) chloride can then be used. Di- and triquinanes (Scheme 3) were made by the stannyl radical approach; the epoxide route was used to prepare a simple propellane (Scheme 4) and in a synthesis of (+)-ceratopicanol (Schemes 5 and 9).