3-(2-methyl-1,3-dioxolan-2-yl)-hexanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-methyl-1,3-dioxolan-2-yl)-hexanal
• 英文别名: 3-(2-Methyl-1,3-dioxolan-2-yl)hexanal
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: GCAGHUONFXPNKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1,3-二氧戊环 、 2-已烯醛 在 二苯甲酮 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 以49%的产率得到3-(2-methyl-1,3-dioxolan-2-yl)-hexanal
  参考文献：
  名称：

  A convenient route to 1,4-monoprotected dialdehydes, 1,4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α,β-unsaturated aldehydes in organic and organic-aqueous media

  摘要：

  alpha,beta-Unsaturated aldehydes were smoothly alkylated by radicals generated through photosensitised hydrogen abstraction of benzophenone. In this way, and by using 1,3-dioxolane as radical precursor, monoprotected 1,4-dialdehydes were obtained from crotonaldehyde, 2-hexenal, 4-methyl-2-pentenal and cyclohexenearboxyaldehyde in a moderate yield, and in a low yield from beta-aryl-alpha,beta-unsaturated aldehydes. With 2-alkyl-1,3-dioxolanes, monoprotected 1,4-ketoaldehydes were analogously prepared. By using methanol, ethanol and isopropanol as radical precursors gamma-lactols were likewise obtained from the above aliphatic aldehydes. These single-step syntheses compared favorably with multi-step approaches previously proposed for some of these compounds. The lactols were conveniently oxidized to the corresponding gamma-lactones. An alternative to the photosensitisation in organic medium was the use of mixed aqueous-organic solvent and a hydrosoluble photosensitiser (benzophenone disodium disulfonate was prepared for this purpose and successfully used), which allowed a more convenient work up. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01659-9

文献信息

• A convenient route to 1,4-monoprotected dialdehydes, 1,4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α,β-unsaturated aldehydes in organic and organic-aqueous media
  作者：Daniele Dondi、Ilaria Caprioli、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1016/s0040-4020(02)01659-9

  日期：2003.2

  alpha,beta-Unsaturated aldehydes were smoothly alkylated by radicals generated through photosensitised hydrogen abstraction of benzophenone. In this way, and by using 1,3-dioxolane as radical precursor, monoprotected 1,4-dialdehydes were obtained from crotonaldehyde, 2-hexenal, 4-methyl-2-pentenal and cyclohexenearboxyaldehyde in a moderate yield, and in a low yield from beta-aryl-alpha,beta-unsaturated aldehydes. With 2-alkyl-1,3-dioxolanes, monoprotected 1,4-ketoaldehydes were analogously prepared. By using methanol, ethanol and isopropanol as radical precursors gamma-lactols were likewise obtained from the above aliphatic aldehydes. These single-step syntheses compared favorably with multi-step approaches previously proposed for some of these compounds. The lactols were conveniently oxidized to the corresponding gamma-lactones. An alternative to the photosensitisation in organic medium was the use of mixed aqueous-organic solvent and a hydrosoluble photosensitiser (benzophenone disodium disulfonate was prepared for this purpose and successfully used), which allowed a more convenient work up. (C) 2003 Elsevier Science Ltd. All rights reserved.