3-[2-(1,3-Dioxolan-2-yl)-ethyl]-bicyclo[3.2.2]-non-8-en-2-on | 183792-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-(1,3-Dioxolan-2-yl)-ethyl]-bicyclo[3.2.2]-non-8-en-2-on
• 英文别名: 7-[2-(1,3-Dioxolan-2-yl)ethyl]bicyclo[3.2.2]non-8-en-6-one；7-[2-(1,3-dioxolan-2-yl)ethyl]bicyclo[3.2.2]non-8-en-6-one
• CAS: 183792-09-8
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: QTECROIJNMWZJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 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[3.2.2]-non-8-en-2-on 在 palladium on activated charcoal 18-冠醚-6 、 硫酸 、 氢气 、 四氯化钛 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 锌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 、 xylene 为溶剂， 反应 64.25h， 生成 (Z)-2-Methyl-5-((1S,5R,6R)-6-methyl-7-methylene-bicyclo[3.2.2]non-6-yl)-pent-2-en-1-ol
  参考文献：
  名称：

  Synthese und Geruch von (E)- und (Z)-bis-homo-�-Santalol

  摘要：

  The synthesis of the title compounds is described. Guided by theoretical considerations and molecular modeling studies, the influence of the bulky group opposite to the osmophorically important primary hydroxyl function on the odour impression is determined. The organoleptic evaluation proved the predicted sandal like odour of the (Z)-isomer and its also predicted absence with (E)-isomer. A moderate increase of the volume of the bulky group shows no influence on the sandalwood odour of the new analogue.

  DOI：

  10.1007/bf00817266
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 Bicyclo<3.2.2>non-8-en-6-one 在 sodium amide 、 六甲基二硅氮烷 作用下， 以 xylene 为溶剂， 以64.7%的产率得到3-[2-(1,3-Dioxolan-2-yl)-ethyl]-bicyclo[3.2.2]-non-8-en-2-on
  参考文献：
  名称：

  Synthese und Geruch von (E)- und (Z)-bis-homo-�-Santalol

  摘要：

  The synthesis of the title compounds is described. Guided by theoretical considerations and molecular modeling studies, the influence of the bulky group opposite to the osmophorically important primary hydroxyl function on the odour impression is determined. The organoleptic evaluation proved the predicted sandal like odour of the (Z)-isomer and its also predicted absence with (E)-isomer. A moderate increase of the volume of the bulky group shows no influence on the sandalwood odour of the new analogue.

  DOI：

  10.1007/bf00817266

文献信息

• Synthese und Geruch von (E)- und (Z)-bis-homo-�-Santalol
  作者：G. Buchbauer、H. Spreitzer、F. Zechmeister-Machhart、C. Haunschmidt、F. Tr�scher

  DOI：10.1007/bf00817266

  日期：——

  The synthesis of the title compounds is described. Guided by theoretical considerations and molecular modeling studies, the influence of the bulky group opposite to the osmophorically important primary hydroxyl function on the odour impression is determined. The organoleptic evaluation proved the predicted sandal like odour of the (Z)-isomer and its also predicted absence with (E)-isomer. A moderate increase of the volume of the bulky group shows no influence on the sandalwood odour of the new analogue.