3-(1,3-dioxolan-2-yl)butyric acid

• 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: 3-(1,3-dioxolan-2-yl)butyric acid
• 英文别名: 3-(1,3-Dioxolan-2-yl)butanoic acid；3-(1,3-dioxolan-2-yl)butanoic acid
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: QRNQOIZJEOTWMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对硝基溴化苄 、 3-(1,3-dioxolan-2-yl)butyric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以30.7 mg的产率得到4-nitrobenzyl 3-(1,3-dioxolan-2-yl)butanoate
  参考文献：
  名称：

  α,β-不饱和羧酸在光激发酮催化下的正式加氢甲酰化

  摘要：

  一种容易获得的噻吨酮衍生物，3,6-二甲氧基-9H-噻吨酮-9-one，已被用作1,3-二氧戊环与α,β-不饱和化合物共轭自由基加成的有效催化剂。

  DOI：

  10.1246/cl.190197
• 作为产物：
  描述：

  3-(1,3-dioxolan-2-yl)-butyraldehyde 在 air 作用下， 以 氘代氯仿 为溶剂， 生成 3-(1,3-dioxolan-2-yl)butyric acid
  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.
• Formal Hydroformylation of α,β-Unsaturated Carboxylic Acids under Photoexcited Ketone Catalysis
  作者：Kailong Zhu、Tsuyoshi Ohtani、Chandra Bhushan Tripathi、Daisuke Uraguchi、Takashi Ooi

  DOI：10.1246/cl.190197

  日期：2019.7.5

  A readily available thioxanthone derivative, 3,6-dimethoxy-9H-thioxanthen-9-one, has been utilized as an effective catalyst for the conjugate radical addition of 1,3-dioxolane to α,β-unsaturated ca...

  一种容易获得的噻吨酮衍生物，3,6-二甲氧基-9H-噻吨酮-9-one，已被用作1,3-二氧戊环与α,β-不饱和化合物共轭自由基加成的有效催化剂。