3-(1,3-dioxolan-2-yl)-butyraldehyde | 161559-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 3-(1,3-dioxolan-2-yl)-butyraldehyde
• 英文别名: 3-(1,3-Dioxolan-2-yl)butanal
• CAS: 161559-09-7
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: WCZRLBLPIWVEBI-UHFFFAOYSA-N

物化性质

• 沸点：
  211.2±15.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (E)-2-methyl-5-phenylpent-4-enal 在 四氧化锇 吡啶 、 lead(IV) acetate 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 5.75h， 生成 3-(1,3-dioxolan-2-yl)-butyraldehyde
  参考文献：
  名称：

  Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles

  摘要：

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.

  DOI：

  10.1021/jo00052a015

文献信息

• Synthesis of γ-lactols, γ-lactones and 1,4-monoprotected succinaldehydes under moderately concentrated sunlight
  作者：Daniele Dondi、Stefano Protti、Angelo Albini、Sonia Mañas Carpio、Maurizio Fagnoni

  DOI：10.1039/b904427b

  日期：——

  The usefulness of solar light for carrying out photocatalytic reactions involving the formation of a carbon–carbon bond has been explored. Thus, some radical alkylations of α,β-unsaturated acids or aldehydes have been carried out in a mixed aqueous solution. Under these conditions, alkyl radicals are generated from i-PrOH and 1,3-dioxolane by photocatalyzed hydrogen abstraction. A water soluble photocatalyst (disodium benzophenondisulfonate, BPSS) was used, which greatly simplifies work up. With reasonably efficient radical traps (e.g. maleic acid), the syntheses could be carried out up to completion on a 10 gram scale within 10–15 hours exposure to sunlight in a solar concentrator (SOLFIN apparatus) in November in Almeria (Spain). The alkylation of some α,β-unsaturated aldehydes have been likewise performed under the same conditions.

  人们已经探索了太阳光在进行涉及碳-碳键形成的光催化反应中的有用性。因此，一些α，β-不饱和酸或醛的自由基烷基化是在混合水溶液中进行的。在这些条件下，i-PrOH 和 1,3-二氧戊环通过光催化夺氢生成烷基自由基。使用水溶性光催化剂（二苯甲酮二磺酸二钠，BPSS），大大简化了操作。借助相当有效的自由基捕获器（例如马来酸），11 月在阿尔梅里亚（西班牙）的太阳能聚光器（SOLFIN 装置）中，在阳光照射下 10-15 小时内即可完成 10 克规模的合成。一些α,β-不饱和醛的烷基化也在相同的条件下进行。
• Henke Brad R., Kouklis Andrew J., Heathcock Clayton H., J. Org. Chem., 57 (1992) N 26, S 7056-7066
  作者：Henke Brad R., Kouklis Andrew J., Heathcock Clayton H.

  DOI：——

  日期：——
• US4044026A
  申请人：——

  公开号：US4044026A

  公开（公告）日：1977-08-23
• 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.
• Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles
  作者：Brad R. Henke、Andrew J. Kouklis、Clayton H. Heathcock

  DOI：10.1021/jo00052a015

  日期：1992.12

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.