3-(2-furanyl)butanal | 49612-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(2-furanyl)butanal
• 英文别名: 3-(Furan-2-yl)butanal
• CAS: 49612-49-9
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: NKNFZLZSPPPCSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.38
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-furanyl)butanal 在 nickel dichloride chromium dichloride 、 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 (E)-ethyl 6-(2-furanyl)-4-oxo-2-heptenoate
  参考文献：
  名称：

  Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

  摘要：

  The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.

  DOI：

  10.1021/jo9721554
• 作为产物：
  描述：

  methyl 3-(2-furyl)acrylate 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 2.5h， 生成 3-(2-furanyl)butanal
  参考文献：
  名称：

  Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

  摘要：

  The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.

  DOI：

  10.1021/jo9721554

文献信息

• Process for the Preparation of Prostaglandin Analogues and Intermediates Thereof
  申请人：Henschke Julian P.

  公开号：US20090259058A1

  公开（公告）日：2009-10-15

  The present application provides intermediates for preparing prostaglandin analogues and processes for preparing prostaglandin analogues and intermediates thereof. The intermediates include: A compound of formula (6): R 1 represents H, C 1 -C 5 -alkyl, or benzyl, in particular isopropyl.

  本申请提供了用于制备前列腺素类似物的中间体以及制备前列腺素类似物和其中间体的方法。这些中间体包括：化合物的公式（6）： R 1 代表H，C 1 -C 5 -烷基，或苄基，特别是异丙基。
• Morpholinium Trifluoroacetate-Catalyzed Aldol Condensation of Acetone with both Aromatic and Aliphatic Aldehydes
  作者：Kristina Zumbansen、Arno Döhring、Benjamin List

  DOI：10.1002/adsc.200900902

  日期：——

  We report a highly efficient, general and practical method for the aldol condensation of acetone with aromatic and aliphatic aldehydes, using morpholinium trifluoroacetate as a catalyst.

  我们报告了一种高效，通用和实用的方法，用于将丙酮与芳香族和脂肪族醛醛醇醛缩合，使用三氟乙酸吗啉鎓作为催化剂。
• Jenner, Gerard; Rimmelin, Jean; Antoni, Francois, Bulletin de la Societe Chimique de France, 1981, vol. 2, # 1-2, p. 65 - 70
  作者：Jenner, Gerard、Rimmelin, Jean、Antoni, Francois、Libs, Suzanne、Schleiffer, Elisabeth

  DOI：——

  日期：——
• US7897795B2
  申请人：——

  公开号：US7897795B2

  公开（公告）日：2011-03-01
• Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates
  作者：Michael E. Jung、Mehrak Kiankarimi

  DOI：10.1021/jo9721554

  日期：1998.5.1

  The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.