3-(3,4,6,6-tetramethyl-2-oxo-1-cyclohex-3-enyl)-propanal | 912843-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3,4,6,6-tetramethyl-2-oxo-1-cyclohex-3-enyl)-propanal
• 英文别名: 3-(3,4,6,6-Tetramethyl-2-oxocyclohex-3-en-1-yl)propanal
• CAS: 912843-99-3
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: WXAWFDRPSSLSOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±21.0 °C(predicted)
• 密度：
  0.938±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3,4,6,6-tetramethyl-2-oxo-1-cyclohex-3-enyl)-propanal 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 31.0h， 生成 (Z)-2-methyl-5-(3,4,6,6-tetramethyl-2-methylen-1-cyclohex-3-enyl)-2-penten-1-ol
  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：

  ethyl-1-[2-(1,3-dioxolan-2-yl)-ethyl]-4,6,6-trimethyl-2-oxo-1-cyclohex-3-enyl-carboxylate 在 氢氧化钾 、 正丁基锂 、 硫酸 、 N-环己基异丙基胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 水 为溶剂， 反应 68.0h， 生成 3-(3,4,6,6-tetramethyl-2-oxo-1-cyclohex-3-enyl)-propanal
  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

文献信息

• Syntheses and odor of “bulky group”-modified sandalwood odorants: isophorono-β-santalol analogues
  作者：J. Höfinghoff、G. Buchbauer、W. Holzer、P. Wolschann

  DOI：10.1016/j.ejmech.2006.03.016

  日期：2006.8

  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.