2-[2-(1,3-dioxolan-2-yl)-ethyl]-3,5,5-trimethylcyclohex-2-en-1-one | 912843-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-(1,3-dioxolan-2-yl)-ethyl]-3,5,5-trimethylcyclohex-2-en-1-one
• 英文别名: 2-[2-(1,3-Dioxolan-2-yl)ethyl]-3,5,5-trimethylcyclohex-2-en-1-one
• CAS: 912843-82-4
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: AICPJTLSYRFQQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  2-[2-(1,3-dioxolan-2-yl)-ethyl]-3,5,5-trimethylcyclohex-2-en-1-one 在 platinum on activated charcoal 三乙胺 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以72.6%的产率得到2-[2-(1,3-dioxolan-2-yl)-ethyl]-3,5,5-trimethylcyclohexan-1-one
  参考文献：
  名称：

  Syntheses and odor of “bulky group”-modified sandalwood odorants: isophorono-β-santalol analogues

  摘要：

  Three osmophoric points have been found to be necessary for the scent of sandalwood odorants. One of these points is the bulky group in a certain distance from the osmophoric hydroxyl group. Such a hydrophobic moiety is part of the trimethylcyclopentenyl derivatives, the so called campholenals, among them many are known to exert a strong and long lasting sandalwood odor. In continuation of our SAR-studies of sandalwood odorants four isophorone analogues of beta-santalol have been synthesized. The hydrophobic region of these new isophorone derivatives is now a trimethylcyclohexene nucleus, so to speak an extension of the cyclopentene part of the campholenals by one methylene group. This modification changes the sandalwood odor drastically to woody odor notes, reminiscent only to sandalwood odor. The environs of the crowded trimethylcyclohexene nucleus demonstrate the sensitivity of sandalwood odor on the shape of the hydrophobic, bulky part of beta-santalol analogues. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.016
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 异佛尔酮 在 sodium amide 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以21.4%的产率得到2-[2-(1,3-dioxolan-2-yl)-ethyl]-3,5,5-trimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  Syntheses and odor of “bulky group”-modified sandalwood odorants: isophorono-β-santalol analogues

  摘要：

  Three osmophoric points have been found to be necessary for the scent of sandalwood odorants. One of these points is the bulky group in a certain distance from the osmophoric hydroxyl group. Such a hydrophobic moiety is part of the trimethylcyclopentenyl derivatives, the so called campholenals, among them many are known to exert a strong and long lasting sandalwood odor. In continuation of our SAR-studies of sandalwood odorants four isophorone analogues of beta-santalol have been synthesized. The hydrophobic region of these new isophorone derivatives is now a trimethylcyclohexene nucleus, so to speak an extension of the cyclopentene part of the campholenals by one methylene group. This modification changes the sandalwood odor drastically to woody odor notes, reminiscent only to sandalwood odor. The environs of the crowded trimethylcyclohexene nucleus demonstrate the sensitivity of sandalwood odor on the shape of the hydrophobic, bulky part of beta-santalol analogues. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.016