5-n-dodecyl-2(3H)-furanone | 83469-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-n-dodecyl-2(3H)-furanone
• 英文别名: 5-dodecylfuran-2(3H)-one；5-dodecyl-3H-furan-2-one
• CAS: 83469-92-5
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: HPHWIBIBURYBSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  色胺 、 5-n-dodecyl-2(3H)-furanone 在 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 (11bS)-11b-dodecyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one 、 (11bR)-11b-dodecyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885
• 作为产物：
  描述：

  trans-2-hexadecen-1-al-4-one 以28%的产率得到
  参考文献：
  名称：

  DAURIA, M.;DE, MICO, A.;PIANCATELLI, G.;SCETTRI, A., TETRAHEDRON, 1982, 38, N 11, 1661-1666

  摘要：

  DOI：

文献信息

• Synergistic Lewis base and anion-binding catalysis for the enantioselective vinylogous addition of deconjugated butenolides to allenoates
  作者：Vikas Kumar、Santanu Mukherjee

  DOI：10.1039/c3cc46858e

  日期：——

  An enantioselective vinylogous umpolung addition of deconjugated butenolides to allenoates has been developed for the first time with the help of synergistic combination of an achiral phosphine and a chiral squaramide, and represents the first example of a catalytic enantioselective Cγ–Cγ bond formation between two different carbonyl partners.

  在无手性膦和手性方酰胺协同作用的帮助下，首次开发出了将脱共轭丁烯内酯与异烯酸酯进行对映选择性乙烯基仲醇加成的方法，这也是在两个不同的羰基伙伴之间催化对映选择性 Cγ-Cγ 键形成的首个实例。
• A facile route to 5-alkyl-2(3H)-furanones by photoisomerisation of enedicarbonyl compounds
  作者：M. D'Auria、A. De Mico、G. Piancatelli、A. Scettri

  DOI：10.1016/0040-4020(82)80143-9

  日期：1982.1

  A new and useful synthesis of a title compounds is reported. They can be obtained easily by photocyclization of enedicarbonyl compounds 3 and 4. A different behaviour, ascribed to the geometry of a double bond, is observed; 3 are converted only to butenolides 5, while trans-isomers 4 are converted into alkyl-furyl-ketones 5 and 6. A possible mechanism is described.

  报道了标题化合物的新的和有用的合成。它们可以通过烯二羰基化合物3和4的光环化而容易地获得。观察到归因于双键的几何形状的不同行为。图3中的化合物仅转化为丁烯内酯5，而反式异构体4则转化为烷基-呋喃酮5和6。描述了一种可能的机制。