2-(2-methyl-3-furanyl)acetic acid | 30012-00-1

• 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: 2-(2-methyl-3-furanyl)acetic acid
• 英文别名: (2-methyl-furan-3-yl)-acetic acid；2-(2-Methylfuran-3-yl)acetic acid
• CAS: 30012-00-1
• 化学式: C₇H₈O₃
• mdl: MFCD19160718
• 分子量: 140.139
• InChiKey: SLTDWNOILKUZKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸糠酯 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 22.08h， 生成 2-(2-methyl-3-furanyl)acetic acid
  参考文献：
  名称：

  Nemoto, Hideo; Shitara, Eiki; Fukumoto, Keiichiro, Heterocycles, 1985, vol. 23, # 3, p. 549 - 551

  摘要：

  DOI：

文献信息

• Intramolecular Carbenoid Insertions:  Reactions of α-Diazo Ketones Derived from Furanyl-, Thienyl-, (Benzofuranyl)-, and (Benzothienyl)acetic Acids with Rhodium(II) Acetate
  作者：Kelvin Yong、Mohamed Salim、Alfredo Capretta

  DOI：10.1021/jo9814593

  日期：1998.12.1

  alpha-Diazo ketones tethered to furan, benzofuran, thiophene, and benzothiophene by a single methylene spacer have been shown to undergo atypical, rhodium(II) acetate catalyzed chemistry. For example, while treatment of 1-diazo-3-(3-furanyl)-2-propanone with Rh-2(OAc)(4) resulted in the expected 2-(4-oxo-2-cyclopentenylidene)acetaldehyde, isomeric 1-diazo-3-(2-furanyl)-2-propanone undergoes a vinylogous Wolff rearrangement and in the presence of water gives a mixture of 6a-methyl-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-one and 2-(2-methyl-3-furyl)acetic acid. Rhodium acetate catalyzed decomposition of 1-diazo-3-(3-benzofuranyl)-2-propanone and 1-diazo-3-(2-benzofuranyl)-2-propanone are also shown to undergo vinylogous Wolff rearrangement despite the fact that this chemistry is not observed with homologous benzofuranyl systems. alpha-Diazo ketones derived from benzothienyl propionic acids undergo the expected cyclization with 1-diazo-4-(3-benzothienyl)-2-butanone and 1-diazo-4-(2-benzothienyl)-2-butanone giving rise to 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-3-one and 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-2-one, respectively. While decomposition of 1-diazo-3-(3-benzothienyl)-2-propanone resulted in the formation of 2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-a-one, the isomeric 1-diazo-3-(2-benzothienyl)-2-propanone gave a dimer which resulted from a [3 + 2] cycloaddition followed by a [1,3]-alkyl shift. Overall, the results from this study of intramolecular carbenoid insertion into five-membered heteroaromatic systems show that the resultant chemistry is dependent on the nature of the heteroatom, position of substitution, and the length of the aliphatic tether.
• NEMOTO, HIDEO;SHITARA, EIKI;FUKUMOTO, KEIICHIRO;KAMETANI, TETSUJI, HETEROCYCLES, 1985, 23, N 3, 549-551
  作者：NEMOTO, HIDEO、SHITARA, EIKI、FUKUMOTO, KEIICHIRO、KAMETANI, TETSUJI

  DOI：——

  日期：——
• Dioxo-tetrahydroquinoline derivatives
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0459561B1

  公开（公告）日：1995-09-20
• US5268378A
  申请人：——

  公开号：US5268378A

  公开（公告）日：1993-12-07