3-oxo-1-butenyl acetate | 13945-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxo-1-butenyl acetate
• 英文别名: 4-acetoxy-3-buten-2-one；4-Acetoxy-but-3-en-2-on；Essigsaeure-(3-oxo-but-1-enyl-ester)；4-acetoxy-but-3-en-2-one；4-Acetoxy-3-buten-2-one；3-oxobut-1-enyl acetate
• CAS: 13945-19-2
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: MHBHMMTWDJHYMH-UHFFFAOYSA-N

物化性质

• 沸点：
  60-61 °C(Press: 0.4 Torr)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-1-butenyl acetate 在 phosphate buffer 、 Burkholderia cepacia PS lipase 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (1RS,6RS)-6-acetyl-3-methylcyclohex-3-en-1-yl acetate
  参考文献：
  名称：

  Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol

  摘要：

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.02.012
• 作为产物：
  描述：

  乙酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 作用下， 生成 3-oxo-1-butenyl acetate
  参考文献：
  名称：

  β-Keto Acetals. II. Synthesis of 3-Methyl- and 3-Phenyl-furans

  摘要：

  DOI：

  10.1021/jo01107a021

文献信息

• Reactions of (2-acylvinyl)trialkylammonium salts with nucleophilic reagents
  作者：A. N. Nesmeyanov、M. I. Rybinskaya

  DOI：10.1007/bf00848707

  日期：1966.10
• Benneche,Tore; Undheim,Kjell, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 8, p. 529 - 532
  作者：Benneche,Tore、Undheim,Kjell

  DOI：——

  日期：——
• β-Keto Acetals. II. Synthesis of 3-Methyl- and 3-Phenyl-furans
  作者：D. M. BURNESS

  DOI：10.1021/jo01107a021

  日期：1956.1
• Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol
  作者：Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Marco Perego、Stefano Serra

  DOI：10.1016/j.tetasy.2006.02.012

  日期：2006.3

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.