(E)-2,7-Dimethyl-octa-2,6-dienoic acid methyl ester | 66052-33-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2,7-Dimethyl-octa-2,6-dienoic acid methyl ester
• 英文别名: (Z)-2,7-Dimethyl-2,6-octadiensaeuremethylester；Methyl-(E)-2,7-dimethyl-2,6-octadienoat；Methyl (E)-2,7-dimethyl-2,6-octadienoate；methyl (2E)-2,7-dimethylocta-2,6-dienoate
• CAS: 66052-33-3
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: KPAGCKZCXNAZPD-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Methyl (Z,E)-farnesoate 、 四氯化碳 生成 (E)-2,7-Dimethyl-octa-2,6-dienoic acid methyl ester
  参考文献：
  名称：

  Synthesis of isoprenoid 1,5-dienes

  摘要：

  含有异戊二烯基1,5-二烯基基团的脂肪族酸可通过α，β-不饱和酸与烯丙基电子亲和体的选择性γ-烷基化反应高产得到。使用从α，β-不饱和酸制备的二铜（I）双烯酸盐控制烷基化的γ-区域选择性。该方法特别适用于合成异戊二烯基1,5-二烯基天然产物，例如通过将松叶酸与戊二烯基溴烷烷基化合成芳烃酸；通过将松叶酸与3,3-二甲基烯丙基溴烷烷基化合成戊二烯酸；通过将丁烯酸与从dl-柠檬烯衍生的烯丙基溴烷烷基化合成dl-兰斯酸。这些产品在合成昆虫信息素、昆虫幼激素和香水成分方面有用。

  公开号：

  US04064150A1

文献信息

• 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.
• Selective .gamma. alkylation of dienolate anions derived from .alpha.,.beta.-unsaturated acids. Applications to the synthesis of isoprenoid olefins
  作者：John A. Katzenellenbogen、Ann L. Crumrine

  DOI：10.1021/ja00432a038

  日期：1976.8
• Synthesis of isoprenoid 1,5-dienes
  申请人：University of Illinois Foundation

  公开号：US04064150A1

  公开（公告）日：1977-12-20

  Aliphatic acids containing an isoprenoid 1,5-diene moiety are prepared in high yields by the selective gamma alkylation of .alpha.,.beta.-unsaturated acids with allylic electrophiles. The gamma-regioselectivity of the alkylation is controlled by the use of the dicopper(I) dienolates prepared from the .alpha.,.beta.-unsaturated acids. The method offers a particularly facile means for synthesizing isoprenoid 1,5-diene natural products such as farnesoic acid by alkylation of senecioic acid with geranyl bromide; geranoic acid by alkylation of senecioic acid with 3,3-dimethallyl bromide; and dl-lanceol by alkylation of tiglic acid with an allylic bromide derived from dl-limonene. Such products find use in the synthesis of insect pheremones, insect juvenile hormones, and components of perfumes.

  含有异戊二烯基1,5-二烯基基团的脂肪族酸可通过α，β-不饱和酸与烯丙基电子亲和体的选择性γ-烷基化反应高产得到。使用从α，β-不饱和酸制备的二铜（I）双烯酸盐控制烷基化的γ-区域选择性。该方法特别适用于合成异戊二烯基1,5-二烯基天然产物，例如通过将松叶酸与戊二烯基溴烷烷基化合成芳烃酸；通过将松叶酸与3,3-二甲基烯丙基溴烷烷基化合成戊二烯酸；通过将丁烯酸与从dl-柠檬烯衍生的烯丙基溴烷烷基化合成dl-兰斯酸。这些产品在合成昆虫信息素、昆虫幼激素和香水成分方面有用。