5,7-dimethyl-oct-6-enal | 55947-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,7-dimethyl-oct-6-enal
• 英文别名: 5,7-Dimethyloct-6-enal
• CAS: 55947-56-3
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: HCMPNZBYQMKTQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-二甲基巴比妥酸 、 5,7-dimethyl-oct-6-enal 在 ethylenediamine Tetraacetic Acid 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以41%的产率得到5-((1R,2S,3R)-2-Isopropenyl-3-methyl-cyclohexyl)-1,3-dimethyl-pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Intra- and intermolecular hetero-Diels-Alder reactions. 45. Simple and induced diastereoselectivity in intramolecular hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes. Experimental data and calculations

  摘要：

  The simple and induced diastereoselectivity of the intramolecular hetero-Diels-Alder reaction of the alkylidene 1,3-dicarbonyl compounds 7a-e, obtained in situ by Knoevenagel condensation of the aldehydes 5a-e and dimethylbarbituric acid 6, was investigated experimentally and theoretically. In all examples the selectivity is very high; thus the domino reaction of 5a and 6 gives nearly exclusively the trans-fused tricyclic dihydropyran 8 (trans/cis = 98.8:1.2). In the similar reactions of the chiral aldehydes 5b-e and 6 the trans-cycloadducts 28, 33, 36, and 41 are the main products out of four possible diastereomers. The induced diastereoselectivity for the reaction of 5b and 5e with 6 is >99:1 and for the reaction of 5e and Sd-with 6, 95.2:3.6 and 94.1:4.7, respectively. Semiempirical AM1 calculations have been used to locate the transition structures of the intramolecular hetero-Diels-Alder reaction of 7a. The results were employed to create new parameters for the MM2-type force-field to determine the transition structures of 7b-e. The obtained data were compared with the experimental results of the cycloadditions and showed an excellent agreement.

  DOI：

  10.1021/jo00080a030
• 作为产物：
  描述：

  4-甲酰基戊酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 反应 57.5h， 生成 5,7-dimethyl-oct-6-enal
  参考文献：
  名称：

  Intra- and intermolecular hetero-Diels-Alder reactions. 45. Simple and induced diastereoselectivity in intramolecular hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes. Experimental data and calculations

  摘要：

  The simple and induced diastereoselectivity of the intramolecular hetero-Diels-Alder reaction of the alkylidene 1,3-dicarbonyl compounds 7a-e, obtained in situ by Knoevenagel condensation of the aldehydes 5a-e and dimethylbarbituric acid 6, was investigated experimentally and theoretically. In all examples the selectivity is very high; thus the domino reaction of 5a and 6 gives nearly exclusively the trans-fused tricyclic dihydropyran 8 (trans/cis = 98.8:1.2). In the similar reactions of the chiral aldehydes 5b-e and 6 the trans-cycloadducts 28, 33, 36, and 41 are the main products out of four possible diastereomers. The induced diastereoselectivity for the reaction of 5b and 5e with 6 is >99:1 and for the reaction of 5e and Sd-with 6, 95.2:3.6 and 94.1:4.7, respectively. Semiempirical AM1 calculations have been used to locate the transition structures of the intramolecular hetero-Diels-Alder reaction of 7a. The results were employed to create new parameters for the MM2-type force-field to determine the transition structures of 7b-e. The obtained data were compared with the experimental results of the cycloadditions and showed an excellent agreement.

  DOI：

  10.1021/jo00080a030

文献信息

• Method for Synthesising Cyclohexenones and the Use of Same in the Perfume Industry
  申请人：V. MANE FILS

  公开号：US20150376103A1

  公开（公告）日：2015-12-31

  The present invention concerns a method for synthesising cyclohexenone and cyclohexenol compounds having specific fragrances and remanence properties, said method consisting in condensing a ketone on an α-methylene-aldehyde in order to obtain, by means of a domino reaction, compounds of formula (I).

  本发明涉及一种合成具有特定香味和残留性能的环己烯酮和环己烯醇化合物的方法，该方法包括在α-亚甲基醛上缩合酮，以通过多米诺反应获得式(I)化合物。
• Cant,P.A.E. et al., Australian Journal of Chemistry, 1975, vol. 28, p. 391 - 397
  作者：Cant,P.A.E. et al.

  DOI：——

  日期：——
• Cant,P.A.E. et al., Australian Journal of Chemistry, 1975, vol. 28, p. 621 - 630
  作者：Cant,P.A.E. et al.

  DOI：——

  日期：——
• PROCÉDÉ DE SYNTHÈSE DE CYCLOHEXÈNONES AINSI QUE LEUR UTILISATION EN PARFUMERIE
  申请人：V. Mane Fils

  公开号：EP2903697A1

  公开（公告）日：2015-08-12
• METHOD FOR SYNTHEZISING CYCLOHEXENONES FOR USE IN THE PERFUME INDUSTRY AND COMPOUNDS OBTAINED THEREBY
  申请人：V. MANE FILS

  公开号：US20170174602A1

  公开（公告）日：2017-06-22

  Cyclohexenone and cyclohexenol compounds are provided having specific fragrances and remanence properties, along with methods for synthesizing these compounds, including obtaining the compound by condensing a ketone on an α-methylene-aldehyde in order to obtain, by means of a domino reaction, compounds of formula (II) as follows: