2-(1-hydroxy-3,3-dimethyl-4-pentenyl)furan | 133420-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(1-hydroxy-3,3-dimethyl-4-pentenyl)furan
• 英文别名: 1-(Furan-2-yl)-3,3-dimethylpent-4-en-1-ol
• CAS: 133420-08-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: WJKHGUQONHACCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  呋喃 、 3,3-二甲基戊-4-烯醛 在 正丁基锂 作用下， 生成 2-(1-hydroxy-3,3-dimethyl-4-pentenyl)furan
  参考文献：
  名称：

  The synthesis of 2,3,3a,4,5,7a-hexahydro-1H-inden-1-ols by intramolecular Diels-Alder reactions of 1,3,8-nonatrien-5-ols. Dependence of product stereochemistry on the substitution pattern

  摘要：

  A short and efficient synthesis of the title compounds is described, starting from readily available alpha,beta-unsaturated carbonyl compounds 5 and beta,gamma-unsaturated ketones 4. Their directed aldol condensation yields the unsaturated hydroxy ketones 6 which are dehydrated to the trienones 7. Although these fail to cyclize on heating, the intramolecular Diels-Alder reaction can be brought about after reduction or alkyllithium addition to the carbonyl group. Alkyl substitution in the positions 1,2,3,5, and 7 has little influence on the ease and yield of cyclization, whereas a methyl group at C-4 hinders it considerably. The title compounds are obtained as mixtures of usually all four stereoisomers, of which one predominates (greater-than-or-equal-to 50%) in most cases. O-Alkylation in 8b has little effect on the isomer distribution. The major isomer of the 6-bromo derivative forms a highly crystalline p-nitrobenzoate 27, which permits stereochemical assignment through X-ray crystallography; for most other products assignments can be made by comparison and further evaluation of their H-1 NMR spectra. The results are discussed in terms of a simple transition state model. The intramolecular Diels-Alder reaction fails when the length of the tethering chain is reduced by one, or when the diene unit becomes part of a furan ring. Trienones 7 are sensitive to autoxidation, of which some products are described.

  DOI：

  10.1021/jo00008a045

文献信息

• KOZIKOWSKI, ALAN P.;TUCKMANTEL, WERNER, J. ORG. CHEM., 56,(1991) N, C. 2826-2837
  作者：KOZIKOWSKI, ALAN P.、TUCKMANTEL, WERNER

  DOI：——

  日期：——
• The synthesis of 2,3,3a,4,5,7a-hexahydro-1H-inden-1-ols by intramolecular Diels-Alder reactions of 1,3,8-nonatrien-5-ols. Dependence of product stereochemistry on the substitution pattern
  作者：Alan P. Kozikowski、Werner Tuckmantel

  DOI：10.1021/jo00008a045

  日期：1991.4

  A short and efficient synthesis of the title compounds is described, starting from readily available alpha,beta-unsaturated carbonyl compounds 5 and beta,gamma-unsaturated ketones 4. Their directed aldol condensation yields the unsaturated hydroxy ketones 6 which are dehydrated to the trienones 7. Although these fail to cyclize on heating, the intramolecular Diels-Alder reaction can be brought about after reduction or alkyllithium addition to the carbonyl group. Alkyl substitution in the positions 1,2,3,5, and 7 has little influence on the ease and yield of cyclization, whereas a methyl group at C-4 hinders it considerably. The title compounds are obtained as mixtures of usually all four stereoisomers, of which one predominates (greater-than-or-equal-to 50%) in most cases. O-Alkylation in 8b has little effect on the isomer distribution. The major isomer of the 6-bromo derivative forms a highly crystalline p-nitrobenzoate 27, which permits stereochemical assignment through X-ray crystallography; for most other products assignments can be made by comparison and further evaluation of their H-1 NMR spectra. The results are discussed in terms of a simple transition state model. The intramolecular Diels-Alder reaction fails when the length of the tethering chain is reduced by one, or when the diene unit becomes part of a furan ring. Trienones 7 are sensitive to autoxidation, of which some products are described.