(4RS)-4,7-Dimethyloct-6-enal | 132927-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4RS)-4,7-Dimethyloct-6-enal
• 英文别名: 4,7-Dimethyloct-6-enal
• CAS: 132927-13-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: NJWZVYIVEHDYQI-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：

  3-溴丙炔 、 (4RS)-4,7-Dimethyloct-6-enal 、 氢溴酸 生成 7,10-Dimethyl-undec-9-en-1-yn-4-ol
  参考文献：
  名称：

  WU, SHIHU;HUANG, BANGZHOU;GAO, XIANG, SYNTH. COMMUN., 20,(1990) N, C. 1279-1286

  摘要：

  DOI：
• 作为产物：
  描述：

  (4RS)-4,7-Dimethyloct-6-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (4RS)-4,7-Dimethyloct-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

• Wu, Shihui; Huang, Bangzhou; Gao, Xiang, Synthetic Communications, 1990, vol. 20, # 9, p. 1279 - 1286
  作者：Wu, Shihui、Huang, Bangzhou、Gao, Xiang

  DOI：——

  日期：——
• WU, SHIHU;HUANG, BANGZHOU;GAO, XIANG, SYNTH. COMMUN., 20,(1990) N, C. 1279-1286
  作者：WU, SHIHU、HUANG, BANGZHOU、GAO, XIANG

  DOI：——

  日期：——
• 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
  作者：Lutz F. Tietze、Holger Geissler、Jens Fennen、Thomas Brumby、Siegbert Brand、Gerhard Schulz

  DOI：10.1021/jo00080a030

  日期：1994.1

  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.