methyl 2-<2-oxo-3-butenyl>-(5E,7)-octadienoate | 221661-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 2-<2-oxo-3-butenyl>-(5E,7)-octadienoate
• 英文别名: methyl (5E)-2-(2-oxobut-3-enyl)octa-5,7-dienoate
• CAS: 221661-26-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: SKODADWLUMCGCG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-<2-oxo-3-butenyl>-(5E,7)-octadienoate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl (4aα,7α,9aβ)-2,4a,5,6,7,8,9,9a-octahydro-9-oxo-1H-benzocycloheptene-7-carboxylate 、 methyl (4aα,7β,9aβ)-2,4a,5,6,7,8,9,9a-octahydro-9-oxo-1H-benzocycloheptene-7-carboxylate 、 methyl (4aβ,7α,9aβ)-2,4a,5,6,7,8,9,9a-octahydro-9-oxo-1H-benzocycloheptene-7-carboxylate
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions. 5 [1] Facile synthesis of an octahydrobenzocycloheptenone derivative utilising intramolecular Diels-Alder reaction

  摘要：

  Undecatrienone 4 was prepared in a short sequence via siloxycyclopropanes 1 and 3. Intramolecular Diels-Alder reaction (IMDA) of 4 under various conditions afforded octahydrobenzocycloheptenone derivative 5 as a mixture of three or four diastereomers. High diastereoselectivities in favour of the endo-product cis-5a could be obtained with TiCl4 as promoter. This selectivities were attributed to the formation of a seven-membered ring chelate as intermediate. The configurational assignment of all four diastereomers of 5 was based on isomerisation reactions and NMR analysis.

  DOI：

  10.1002/(sici)1521-3897(199902)341:2<173::aid-prac173>3.0.co;2-m
• 作为产物：
  描述：

  c-2-(Trimethylsiloxy)-t-2-vinyl-r-1-cyclopropancarbonsaeure-methylester 在 1,3-二甲基-2-咪唑啉酮 、 triethylamine tris(hydrogen fluoride) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 methyl 2-<2-oxo-3-butenyl>-(5E,7)-octadienoate
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions. 5 [1] Facile synthesis of an octahydrobenzocycloheptenone derivative utilising intramolecular Diels-Alder reaction

  摘要：

  Undecatrienone 4 was prepared in a short sequence via siloxycyclopropanes 1 and 3. Intramolecular Diels-Alder reaction (IMDA) of 4 under various conditions afforded octahydrobenzocycloheptenone derivative 5 as a mixture of three or four diastereomers. High diastereoselectivities in favour of the endo-product cis-5a could be obtained with TiCl4 as promoter. This selectivities were attributed to the formation of a seven-membered ring chelate as intermediate. The configurational assignment of all four diastereomers of 5 was based on isomerisation reactions and NMR analysis.

  DOI：

  10.1002/(sici)1521-3897(199902)341:2<173::aid-prac173>3.0.co;2-m

文献信息

• Intramolecular Diels-Alder reactions. 5 [1] Facile synthesis of an octahydrobenzocycloheptenone derivative utilising intramolecular Diels-Alder reaction
  作者：Barbara Frey、Hans-Ulrich Reißig

  DOI：10.1002/(sici)1521-3897(199902)341:2<173::aid-prac173>3.0.co;2-m

  日期：1999.2

  Undecatrienone 4 was prepared in a short sequence via siloxycyclopropanes 1 and 3. Intramolecular Diels-Alder reaction (IMDA) of 4 under various conditions afforded octahydrobenzocycloheptenone derivative 5 as a mixture of three or four diastereomers. High diastereoselectivities in favour of the endo-product cis-5a could be obtained with TiCl4 as promoter. This selectivities were attributed to the formation of a seven-membered ring chelate as intermediate. The configurational assignment of all four diastereomers of 5 was based on isomerisation reactions and NMR analysis.