4,5,6,7-tetrahydrocyclopenta-1,3-dioxin-4-one | 32961-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6,7-tetrahydrocyclopenta-1,3-dioxin-4-one
• 英文别名: 2,2-dimethyl-6,7-dihydro-5H-cyclopenta[1,3]dioxin-4-one；2,2-dimethyl-6,7-dihydro-5H-cyclopenta[d][1,3]dioxin-4-one
• CAS: 32961-64-1
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: ZBAWQNCLJFFUKY-UHFFFAOYSA-N

物化性质

• 沸点：
  295.8±29.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4,5,6,7-tetrahydrocyclopenta-1,3-dioxin-4-one 以 四氯化碳 为溶剂， 生成 2-甲氧羰基环戊酮
  参考文献：
  名称：

  Direct observation of .alpha.-oxo ketenes from the photolysis of .alpha.-diazo .beta.-diketones

  摘要：

  Monitoring by IR spectroscopy of the broad-band irradiation of the symmetrically substituted 2-diazo-cyclohexane-1,3-dione (I 1), 3-diazopentane-2,4-dione (19), and 4-diazo-2,2,6,6-tetramethylheptane-3,5-dione (24) in Ar matrices at 12 K showed the formation of 2-carbonylcyclopentanone (s-Z-12), acetyl(methyl)ketene (s-E-20), and tert-butyl(pivaloyl)ketene (s-E-25), respectively, in less than 10 min. On increasing the photolysis time to >3 h, the alpha-oxo ketenes 12,20, and 25 decarbonylated to the corresponding oxocarbenes which underwent Wolff rearrangement to carbonylcyclobutane (15), dimethylketene (23), and di-tert-butylketene (28), respectively. The reaction of 2-carbonylcyclopentanone (12) with CH3OH was monitored by IR spectroscopy. Thus, it was found that the reaction started at ca. 100 K and was essentially complete at 140 K, involving the initial formation of the enol form (9) of methyl 2-oxocyclopentanecarboxylate.

  DOI：

  10.1021/jo00044a019
• 作为产物：
  描述：

  环戊酮 在 六甲基磷酰三胺 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 三氟乙酸 为溶剂， 反应 13.0h， 生成 4,5,6,7-tetrahydrocyclopenta-1,3-dioxin-4-one
  参考文献：
  名称：

  一种合成二氧杂环戊烯酮与茴香酸氰基甲酸酯羧化酮烯酸酯的新方法

  摘要：

  我们描述的分子内二氧戊烯酮光环加成反应的普遍性取决于所需官能化的二氧杂环戊烯酮的可用性。我们在此报告了通过酮烯酸酯与茴香基氰基甲酸酯的羧化以及所得酮酯与丙酮的缩合来制备二氧杂环戊酮的一般方法。

  DOI：

  10.1016/s0040-4039(00)95908-2

文献信息

• Sythesis of 1,3-dioxin-4-ones and their use in synthesis. XVIII. Synthesis of azetidin-2-ones from 1,3-dioxin-4-ones via 3-hydroxycarboxamides.
  作者：Jun-ichi SAKAKI、Satoshi KOBAYASHI、Masayuki SATO、Chikasra KANEKO

  DOI：10.1248/cpb.37.2952

  日期：——

  A general method for the synthesis of azetidin-2-ones from 1, 3-dioxin-4-ones is described. The method consists of 1) the formatin of β-ketocarboxamides, 2) their reduction to 3-hydroxycarboxamides, 3) mesylationg, and 4) base-mediated cyclization of 3-mesyloxycarboxamides to the final azetidinones. Stereochemical demand in the cyclizatino step has been clarified by using 5, 6-tri- and -tetramethylene derivatives of 2, 2-dimethyl-1, 3-dioxin-4-one. Microbiological reduction of the acetoacetamides by baker's yeast gave (S)-3-hydroxybutanamides of ≥98% optical purity, whose cyclization afforded (R)-4-methylazetidin-2-ones.

  描述了一种从1,3-二氧戊环-4-酮合成氮杂环丁-2-酮的一般方法。该方法包括：1）形成β-酮羧酰胺，2）将其还原为3-羟基羧酰胺，3）甲磺酰化，以及4）3-甲磺酰氧基羧酰胺在碱介导下环化，得到最终的氮杂环丁酮。通过使用2,2-二甲基-1,3-二氧戊环-4-酮的5,6-三甲基和四甲基衍生物，阐明了环化步骤中的立体化学需求。利用面包酵母对乙酰乙酰胺进行微生物还原，得到了光学纯度≥98%的(S)-3-羟基丁酰胺，其环化产物为(R)-4-甲基氮杂环丁-2-酮。
• Jaeger,G.; Wenzelburger,J., Justus Liebigs Annalen der Chemie, 1976, p. 1689 - 1712
  作者：Jaeger,G.、Wenzelburger,J.

  DOI：——

  日期：——
• Jaeger,G., Chemische Berichte, 1972, vol. 105, p. 137 - 149
  作者：Jaeger,G.

  DOI：——

  日期：——
• US3931171A
  申请人：——

  公开号：US3931171A

  公开（公告）日：1976-01-06
• Direct observation of .alpha.-oxo ketenes from the photolysis of .alpha.-diazo .beta.-diketones
  作者：Regis Leung-Toung、Curt Wentrup

  DOI：10.1021/jo00044a019

  日期：1992.8

  Monitoring by IR spectroscopy of the broad-band irradiation of the symmetrically substituted 2-diazo-cyclohexane-1,3-dione (I 1), 3-diazopentane-2,4-dione (19), and 4-diazo-2,2,6,6-tetramethylheptane-3,5-dione (24) in Ar matrices at 12 K showed the formation of 2-carbonylcyclopentanone (s-Z-12), acetyl(methyl)ketene (s-E-20), and tert-butyl(pivaloyl)ketene (s-E-25), respectively, in less than 10 min. On increasing the photolysis time to >3 h, the alpha-oxo ketenes 12,20, and 25 decarbonylated to the corresponding oxocarbenes which underwent Wolff rearrangement to carbonylcyclobutane (15), dimethylketene (23), and di-tert-butylketene (28), respectively. The reaction of 2-carbonylcyclopentanone (12) with CH3OH was monitored by IR spectroscopy. Thus, it was found that the reaction started at ca. 100 K and was essentially complete at 140 K, involving the initial formation of the enol form (9) of methyl 2-oxocyclopentanecarboxylate.