3-(2-methyl-3-oxo-bicyclo[2.2.1]heptan-2-yl)propanal | 131726-08-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(2-methyl-3-oxo-bicyclo[2.2.1]heptan-2-yl)propanal
• 英文别名: 2-keto-ekasantalal；(1R,2S)-3-(2-methyl-3-oxobicyclo<2.2.1>hept-2-yl)propanal
• CAS: 131726-08-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: IBAKHWUUXNNKEP-NGZCFLSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(2-methyl-3-oxo-bicyclo[2.2.1]heptan-2-yl)propanal 在 18-冠醚-6 四氯化钛 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 生成 (Z)-5-(2-methyl-3-methylene-bicyclo[2.2.1]hept-2-yl)-2-ethyl-pent-2-enol
  参考文献：
  名称：

  Synthesis and olfactoric activity of side-chain modified β-santalol analogues

  摘要：

  Three osmophoric points have been postulated to be necessary for the sandalwood scent of beta -santalol derivatives. One of these points, close to the hydroxyl group, is highly specific on the stereochemistry and, in particular, on the molecular shape. The role of the 2-methyl group in the side chain of beta -santalol derivatives was studied by replacement through a hydrogen atom, an ethyl or an isopropyl group. It turns out that any change at the 2-methyl substituent leads to the complete loss of sandalwood odour. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01271-5
• 作为产物：
  描述：

  3-[2-(1,3-dioxolan-2-yl)ethyl]-bicyclo[2.2.1]heptan-2-one 在 硫酸 、 sodium amide 、 六甲基二硅氮烷 作用下， 以 乙醚 、 xylene 为溶剂， 生成 3-(2-methyl-3-oxo-bicyclo[2.2.1]heptan-2-yl)propanal
  参考文献：
  名称：

  Synthesis and olfactoric activity of side-chain modified β-santalol analogues

  摘要：

  Three osmophoric points have been postulated to be necessary for the sandalwood scent of beta -santalol derivatives. One of these points, close to the hydroxyl group, is highly specific on the stereochemistry and, in particular, on the molecular shape. The role of the 2-methyl group in the side chain of beta -santalol derivatives was studied by replacement through a hydrogen atom, an ethyl or an isopropyl group. It turns out that any change at the 2-methyl substituent leads to the complete loss of sandalwood odour. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01271-5

文献信息

• Krotz, Achim; Helmchen, Guenter, Liebigs Annalen der Chemie, 1994, # 6, p. 601 - 610
  作者：Krotz, Achim、Helmchen, Guenter

  DOI：——

  日期：——
• Total syntheses of sandalwood fragrances: (Z)- and (E)-β-santalol and their enantiomers, ent-β-santalene
  作者：Achim Krotz、Günter Helmchen

  DOI：10.1016/s0957-4166(00)80544-3

  日期：1990.1
• Synthesis and olfactoric activity of keto-β-santalol and methoxy-β-santalol
  作者：Gerhard Buchbauer、Helmut Spreitzer、Friederike Zechmeister-Machhart、Alexander Klinsky、Petra Weiβ-Greiler、Peter Wolschann

  DOI：10.1016/s0223-5234(98)80047-0

  日期：1998.6

  In extension of structure-activity relationship investigations on beta-santalol, where the shape of the molecular surface was found to be of high importance, the influence of the electrostatic properties cf the molecules was investigated. Two derivatives of beta-santalol with similar molecular shape but with an oxygen atom instead of carbon atoms were synthesized: keto-beta-santalol and methoxy-beta-santalol. These two oxygen-containing santalol analogues were synthesized by total syntheses starting from apocamphenilone. A common intermediate for both target molecules, an appropriate bicyclic ketoaldehyde, proved to be inapplicable. Therefore methoxy-beta-santalol was prepared by insertion of an ethyldioxolane sidechain into apocamphenilone and completing the synthesis by five additional steps. Keto-beta-santalol was prepared on a convergent route by insertion of the already prefabricated sidechain into the starting ketone, followed by one additional step. The presence of the second oxygen atom leads to the complete loss of the odour, which is the evidence that apart from the molecular shape, the electrostatic potential has to be taken into account in molecular similarity studies of this class of compounds. (C) Elsevier, Paris.