4-Bromo-3-butyl-5-methyl-2(5H)-furanone | 162285-76-9

• 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: 4-Bromo-3-butyl-5-methyl-2(5H)-furanone
• 英文别名: 3-bromo-4-butyl-2-methyl-2H-furan-5-one
• CAS: 162285-76-9
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: UGWBBDQPNDSJHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-Bromo-3-butyl-5-methyl-2(5H)-furanone 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 生成 4,5-Dibromo-3-(1-bromobutyl)-5-methyl-2(5H)-furanone 、 4-Bromo-3-(1-bromobutyl)-5-hydroxy-5-methyl-2(5H)-furanone
  参考文献：
  名称：

  Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

  摘要：

  Treatment of gamma-monosubstituted allenic esters with N-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (1a), acetoxyfimbrolide (1c), and bromobeckerelide (2a).

  DOI：

  10.1021/jo00111a045
• 作为产物：
  描述：

  Methyl 2-butyl-2,3-pentadienoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 反应 16.0h， 以3%的产率得到5-hydroxy-5-methyl-4-bromo-3-n-butyl-2(5H)-furanone
  参考文献：
  名称：

  Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

  摘要：

  Treatment of gamma-monosubstituted allenic esters with N-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (1a), acetoxyfimbrolide (1c), and bromobeckerelide (2a).

  DOI：

  10.1021/jo00111a045

文献信息

• METHOD FOR DIRECTLY CONSTRUCTING TETRA-SUBSTITUTED ALLENIC ACID COMPOUND HAVING HIGH OPTICAL ACTIVITY
  申请人：Fudan University

  公开号：EP3896053A1

  公开（公告）日：2021-10-20

  The present invention discloses a method for directly constructing highly optically active tetrasubstituted allenic acid compounds, i.e., a one-step process for directly constructing highly optically active axially chiral tetrasubstituted allenic acid compounds by using tertiary propargyl alcohol, carbon monoxide and water as reactants in an organic solvent in the presence of palladium catalyst, chiral diphosphine ligand, monophosphine ligand and organic phosphoric acid. The method of the present invention has the following advantages: operations are simple, raw materials and reagents are readily available, the reaction conditions are mild, the substrate has high universality, the functional group has good compatibility, and the reaction has high enantioselectivity (90%∼> 99% ee). The highly optically active allenic acid compounds obtained by the present invention can be used as an important intermediate to construct γ-butyrolactone compounds containing tetrasubstituted chiral quaternary carbon centers, tetrasubstituted allenic alcohol and other compounds.

  本发明公开了一种直接构建高光学活性的四取代亚砷酸化合物的方法，即在有机溶剂中，在钯催化剂、手性二膦配体、单膦配体和有机磷酸存在下，以叔丙炔醇、一氧化碳和水为反应物，一步法直接构建高光学活性的轴向手性四取代亚砷酸化合物。本发明的方法具有以下优点：操作简单，原料和试剂易得，反应条件温和，底物通用性强，官能团相容性好，反应的对映体选择性高（90%∼> 99% ee）。本发明得到的高光学活性的别烯酸化合物可作为一种重要的中间体，用于构建含有四取代手性季碳中心的γ-丁内酯化合物、四取代别烯醇和其他化合物。
• Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide
  作者：Pedro de March、Josep Font、Antonio Gracia、Zheng Qingying

  DOI：10.1021/jo00111a045

  日期：1995.3

  Treatment of gamma-monosubstituted allenic esters with N-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (1a), acetoxyfimbrolide (1c), and bromobeckerelide (2a).

表征谱图