3-(2-[1,3]Dioxolan-2-yl-ethyl)-bicyclo[2.2.2]octan-2-one | 197150-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 3-(2-[1,3]Dioxolan-2-yl-ethyl)-bicyclo[2.2.2]octan-2-one
• 英文别名: 3-[2-(1,3-Dioxolan-2-yl)ethyl]bicyclo[2.2.2]octan-2-one；3-[2-(1,3-dioxolan-2-yl)ethyl]bicyclo[2.2.2]octan-2-one
• CAS: 197150-02-0
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: CHHLLDAKJVOAIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-[1,3]Dioxolan-2-yl-ethyl)-bicyclo[2.2.2]octan-2-one 在 18-冠醚-6 硫酸 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 4.0h， 生成 5-(3-Oxo-2-methyl-bicyclo[2.2.2]oct-2-yl)-2-methyl-2-pentensaeureethylester
  参考文献：
  名称：

  (Z)-homo-?-Santalol: Synthese und Geruch

  摘要：

  The synthesis of the title compound is described. Starting with the a-alkylation of homo-norcamphor followed by a I Wittig reaction, a Tebbe transformation, and a DIBAH ester-reduction as the most important reactions of a 5 step sequence, (Z)-homo-beta-santalol was obtained, which exhibits the typical precious sandalwood odour. The moderate increase of the volume of the bulky group obviously does not alter the odour quality ''sandalwood'' of this new beta-santalol analogue.

  DOI：

  10.1007/bf00807592
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 双环[2.2.2]辛烷-3-酮 在 sodium amide 、 六甲基二硅氮烷 作用下， 生成 3-(2-[1,3]Dioxolan-2-yl-ethyl)-bicyclo[2.2.2]octan-2-one
  参考文献：
  名称：

  (Z)-homo-?-Santalol: Synthese und Geruch

  摘要：

  The synthesis of the title compound is described. Starting with the a-alkylation of homo-norcamphor followed by a I Wittig reaction, a Tebbe transformation, and a DIBAH ester-reduction as the most important reactions of a 5 step sequence, (Z)-homo-beta-santalol was obtained, which exhibits the typical precious sandalwood odour. The moderate increase of the volume of the bulky group obviously does not alter the odour quality ''sandalwood'' of this new beta-santalol analogue.

  DOI：

  10.1007/bf00807592

文献信息

• (Z)-homo-?-Santalol: Synthese und Geruch
  作者：G. Buchbauer、H. Spreitzer、U. Koller

  DOI：10.1007/bf00807592

  日期：——

  The synthesis of the title compound is described. Starting with the a-alkylation of homo-norcamphor followed by a I Wittig reaction, a Tebbe transformation, and a DIBAH ester-reduction as the most important reactions of a 5 step sequence, (Z)-homo-beta-santalol was obtained, which exhibits the typical precious sandalwood odour. The moderate increase of the volume of the bulky group obviously does not alter the odour quality ''sandalwood'' of this new beta-santalol analogue.