2-methyl-3-pentanoylfuran | 137304-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-pentanoylfuran
• 英文别名: 1-(2-Methylfuran-3-yl)pentan-1-one
• CAS: 137304-19-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: MPTWFOHVEPEVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-methyl-3-pentanoylfuran 在 氨 、 sodium 、 溶剂黄146 作用下， 反应 1.0h， 以70%的产率得到3-(1-hydroxypentyl)-2-methylfuran
  参考文献：
  名称：

  杂环化合物的桦木还原。IV †。3-酰基呋喃的桦木还原。环还原，羰基还原和二聚体形成之间的竞争

  摘要：

  描述了3-酰基呋喃1、3和10的桦木还原及其反应途径。

  DOI：

  10.1002/jhet.5570350608
• 作为产物：
  描述：

  3-糠酸 在 正丁基锂 、 氘代甲醇-d 作用下， 反应 2.0h， 生成 2-methyl-3-pentanoylfuran
  参考文献：
  名称：

  Yu, Shuyuan; Keay, Brian A., Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2600 - 2601

  摘要：

  DOI：

文献信息

• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2.¹ Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings
  作者：Edward Bures、James A. Nieman、Shuyuan Yu、Patrick G. Spinazzé、Jean-Louis J. Bontront、Ian R. Hunt、Arvi Rauk、Brian A. Keay

  DOI：10.1021/jo971098b

  日期：1997.12.1

  A new method for the preparation of 3,4- and 2,5-disubstituted furan rings is described. A variety of 2-silylated-3-(hydroxymethyl)furans and 2-silylated-3-furoic acids lithiate exclusively at C-4 when treated with 2.2 equivs of BuLi. The resulting dianions were quenched with a variety of electrophiles to provide 2-silylated-3-(hydroxymethyl)-substituted furans and 2-silylated-4-substituted 3-furoic acids in good to excellent yields. Removal of the silyl group (n-Bu4NF) provided a variety of 4-substituted-3-(hydroxymethyl)furans and methyl 4-substituted-3-furoates, respectively. The latter esters were prepared due to difficulties encountered in isolating 4-substituted-3-furoic acids. The site of lithiation was altered by protecting the 3-hydroxyl group with a triethylsilane. Lithiation of 2-silylated-3-(((triethylsilyl)oxy)methyl)furan with 1.2 equivs of BuLi followed by the addition of electrophiles provided 2-silylated-3-(((triethylsilyl)oxy)methyl)-5-substituted furan rings. Subsequent removal of both silyl groups provided 2,4-disubstituted furan rings in moderate to good yields. A rationale is provided to explain why protection of the hydroxyl group at C-3 leads to a change in lithiation from the C-4 to the C-5 position of the furan ring. In addition, an explanation for the observed effect of adding HMPA or LiCl to the solution during the lithiation of 2-(tert-butyldimethylsilyl)-3-(hydroxymethyl)furan is provided.
• Yu, Shuyuan; Keay, Brian A., Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2600 - 2601
  作者：Yu, Shuyuan、Keay, Brian A.

  DOI：——

  日期：——
• The birch reduction of heterocyclic compounds.<b>IV</b>. Birch reduction of 3-acylfurans. Competition between ring reduction, carbonyl reduction, and dimer formation
  作者：Daisuke Takano、Yoshitaka Nakajima、Ikuko Miyahara、Ken Hirotsu、Rika Tanaka、Keiji Okada、Yoshiki Morimoto、Takamasa Kinoshita、Kazuo Yoshihara

  DOI：10.1002/jhet.5570350608

  日期：1998.11

  The Birch reduction of 3-acylfurans 1, 3 and 10 and their reaction path ways are described.

  描述了3-酰基呋喃1、3和10的桦木还原及其反应途径。