6-heptyl-2,2-dimethyl-4H-1,3-dioxin-4-one | 662151-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-heptyl-2,2-dimethyl-4H-1,3-dioxin-4-one
• 英文别名: 6-heptyl-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 662151-99-7
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: BFGCNBLVNXZUJG-UHFFFAOYSA-N

物化性质

• 沸点：
  326.2±31.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  6-heptyl-2,2-dimethyl-4H-1,3-dioxin-4-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 5-Methyl-3-octanoyl-furan-2,4-dione
  参考文献：
  名称：

  Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids

  摘要：

  3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin alpha-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric beta-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.

  DOI：

  10.1023/b:rujo.0000003193.75790.de
• 作为产物：
  描述：

  6,6-Dimethyl-3-octanoyl-dihydro-pyran-2,4-dione 在 丙酮 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以71%的产率得到6-heptyl-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids

  摘要：

  3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin alpha-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric beta-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.

  DOI：

  10.1023/b:rujo.0000003193.75790.de

文献信息

• Versatile Synthesis of Acylfuranones by Reaction of Acylketenes with α-Hydroxy Ketones: Application to the One-Step Multicomponent Synthesis of Cadiolide B and Its Analogues
  作者：Philippe Alexandre Peixoto、Agathe Boulangé、Stéphane Leleu、Xavier Franck

  DOI：10.1002/ejoc.201300166

  日期：2013.6

  Functionalized acylfuranones have been prepared in a one-step procedure by thermal fragmentation of the corresponding dioxinones in the presence of hydroxy ketones in basic conditions. Multicomponent reactions also occur on addition of an aldehyde as a third reaction partner resulting in an expeditious access to cadiolide B and its analogues.

  在碱性条件下，在羟基酮的存在下，通过相应的二恶英酮的热裂解，以一步法制备了官能化的酰基呋喃酮。添加醛作为第三个反应伙伴时也会发生多组分反应，从而快速获得卡地内酯 B 及其类似物。
• Design and Synthesis of Epicocconone Analogues with Improved Fluorescence Properties
  作者：Philippe A. Peixoto、Agathe Boulangé、Malcolm Ball、Bertrand Naudin、Thibault Alle、Pascal Cosette、Peter Karuso、Xavier Franck

  DOI：10.1021/ja506914p

  日期：2014.10.29

  product by an aromatic ring. This design element is general and the synthesis is straightforward, providing ready access to libraries of polyfunctional fluorophores with long Stokes shifts based on the epicocconone core. Our structural modifications resulted in analogues with increased photostability and quantum yields compared with the natural product. Staining proteomic gels with these new analogues

  Epicocconone 是一种天然的潜在荧光团，由于其较大的斯托克斯位移和在未结合状态下缺乏荧光而广泛用于生物技术。然而，epicocconone 的低光稳定性和量子产率限制了其更广泛的应用，并且在没有全合成的情况下，这种限制一直是一个长期存在的问题。在这里，我们报告了一种合成 Epiocconone 类似物的一般策略，该策略依赖于 2-碘氧基苯甲酸介导的脱芳构化和用芳香环替换天然产物的三烯尾。这种设计元素是通用的，合成很简单，可以随时访问基于epicocconone 核心的具有长斯托克斯位移的多功能荧光团库。与天然产物相比，我们的结构修改导致类似物具有更高的光稳定性和量子产率。用这些新类似物对蛋白质组凝胶染色显示检测限显着降低，检测到的低丰度蛋白质数量增加了 30%。这些epiccoconone 类似物将大大提高蛋白质组大海捞针中生物标志物针的发现率。
• Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products
  作者：Joshua B. Pyser、Summer A. Baker Dockrey、Attabey Rodríguez Benítez、Leo A. Joyce、Ren A. Wiscons、Janet L. Smith、Alison R. H. Narayan

  DOI：10.1021/jacs.9b09385

  日期：2019.11.20

  Selective access to a targeted isomer is often critical in the synthesis of biologically active molecules. Whereas small-molecule reagents and catalysts often act with anticipated site- and stereoselectivity, this predictability does not extend to enzymes. Further, the lack of access to catalysts that provide complementary selectivity creates a challenge in the application of biocatalysis in synthesis

  在生物活性分子的合成中，选择性地获取目标异构体通常是至关重要的。尽管小分子试剂和催化剂通常具有预期的位点和立体选择性，但这种可预测性并没有扩展到酶。此外，缺乏提供互补选择性的催化剂给生物催化在合成中的应用带来了挑战。在这里，我们报告了一种获得与蛋白质工程正交的具有互补选择性的生物催化剂的方法。通过使用序列相似性网络（SSN），选择了多个序列，并评估了相应的生物催化剂的反应性和选择性。确定了许多具有互补位点和立体选择性的生物催化剂，这些催化剂用于 azaphilone 天然产物的立体发散化学酶合成。具体而言，首次合成了 trichoflectin、deflectin-1a 和月桂酸 A。此外，这些 azaphilones 的化学酶促合成提供了富含对映体的材料，用于基于旋光、CD 光谱和 X 射线晶体学重新分配 trichoflectin 和 deflectin-1a 的绝对构型。