2(5H)-呋喃酮,3-辛基- | 124083-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 2(5H)-呋喃酮,3-辛基-
• 英文名称: 5-n-octyl-2(5H)-furanone
• 英文别名: 3-octyl-5H-furan-2-one；3-octylfuran-2(5H)-one；4-octyl-2H-furan-5-one
• CAS: 124083-32-5
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: FOYYVKFKVOHANS-UHFFFAOYSA-N

物化性质

• 熔点：
  27 °C
• 沸点：
  320.5±11.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Octanoyl-furan-2,4-dione 在 盐酸 、 silica gel 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 2(5H)-呋喃酮,3-辛基-
  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

• The bioinspired design of a reagent allows the functionalization of C_α–H of α,β-unsaturated carbonyl compounds via the Baylis–Hillman chemistry under ambient conditions
  作者：Palwinder Singh、Arun Kumar、Sukhmeet Kaur、Jagroop Kaur、Harpreet Singh

  DOI：10.1039/c5cc08830e

  日期：——

  A rationally designed reagent capable to affect alkylation at C[small alpha] of [small alpha], [small beta]-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-Bond...

  报道了合理设计的试剂，其能够影响[小α]，[小β]-不饱和羰基化合物的C [小α]处的烷基化。反应在室温下进行，没有任何添加剂。pH和H键...
• A new efficient synthesis of alkyl substituted Δ 2 -butenolides
  作者：Felix S Pashkovsky、Yadviga M Katok、Tatyana S Khlebnicova、Fedor A Lakhvich

  DOI：10.1016/s0040-4039(01)00534-2

  日期：2001.5

  A new three-step route to 2-alkyl substituted Δ2-butenolides from 3-alkyltetronic acids is described.

  一种新的三步路线2 -烷基取代的Δ 2个从3- alkyltetronic酸-butenolides进行说明。
• Practical Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols in 2,4,6-Collidine Leading to α,β-Unsaturated Lactones: Concise Stereoselective Synthesis of (+)-Isomintlactone
  作者：Masayoshi Tsubuki、Kazunori Takahashi、Toshio Honda

  DOI：10.1021/jo8025127

  日期：2009.2.6

  We have found that ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine under atmospheric pressure of carbon monoxide smoothly proceeds to afford alpha,beta-unsaturated five- and six-membered lactones in moderate to good yields. Furthermore, we have completed a highly stereoselective synthesis of (+)-isomintlactone by the cyclocarbonylation of allenyl alcohol using 2,4,6-collidine.
• Nitrodienic-like reactivity of 2-nitrofuran with organometallic reagents: one-step synthesis of alkylfuranones
  作者：Angelo Pecunioso、Elena Galoppini、Rita Menicagli

  DOI：10.1016/s0040-4020(01)89063-3

  日期：1990.1
• Menicagli, Rita; Pecunioso, Angelo; Galoppini, Elena, Gazzetta Chimica Italiana, 1989, vol. 119, # 2, p. 141 - 142
  作者：Menicagli, Rita、Pecunioso, Angelo、Galoppini, Elena

  DOI：——

  日期：——