2-acetyl-3-propyl-pent-4-enoic acid methyl ester | 283610-82-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-acetyl-3-propyl-pent-4-enoic acid methyl ester
• 英文别名: methyl 2-acetyl-3-vinylhexanoate；Methyl 2-acetyl-3-ethenylhexanoate
• CAS: 283610-82-2
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: DUVSQTBXBRKVAK-UHFFFAOYSA-N

物化性质

• 沸点：
  245.3±20.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  2-acetyl-3-propyl-pent-4-enoic acid methyl ester 在 碘 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以84%的产率得到(4S,5S)-5-Iodomethyl-2-methyl-4-propyl-4,5-dihydro-furan-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Iodoenolcyclization of 2-Allyl Substituted b-Keto Esters under Thermodynamic Conditions

  摘要：

  An improved procedure for the synthesis of diastereo-enriched tetrasubstituted 4,5-dihydrofurans by using I-2-induced enolcyclization of beta-keto esters is reported. The reactions using I-2 in anhydrous MeCN are considered under thermodynamic control and the more stable trans isomers are preferentially produced.

  DOI：

  10.3987/com-04-10081
• 作为产物：
  描述：

  乙酰乙酸甲酯 在 哌啶 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 5.08h， 生成 2-acetyl-3-propyl-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans

  摘要：

  A two step synthetic strategy for obtaining 2-alkenyl-1,3-dicarbonyl compounds from the corresponding 1,3-dicarbonyl compounds is reported. The method is based on a Knoevenagel condensation and a Michael addition using a high order organocuprate procedure, and proves to be of general value, Obtained compounds are useful starting materials for the synthesis of furan derivatives, (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01173-5

文献信息

• Regioselective Rhodium-Catalyzed Addition of β-Keto Esters, β-Keto Amides, and 1,3-Diketones to Internal Alkynes
  作者：Thorsten M. Beck、Bernhard Breit

  DOI：10.1002/ejoc.201601230

  日期：2016.12

  The first rhodium-catalyzed regioselective addition of 1,3-dicarbonyl compounds, including β-keto esters, β-keto amides, and 1,3-diketones, to internal alkynes furnishes branched allylic compounds. By applying RhI/DPEphos/TFA as the catalytic system, aliphatic as well as aromatic internal methyl-substituted alkynes act as suitable substrates to yield valuable branched α-allylated 1,3-dicarbonyl compounds

  第一铑催化的区域选择性加入1,3-二羰基化合物，包括β酮酯，β - 酮酰胺和1,3-二酮，到内部炔烃配料支链的烯丙基化合物。通过应用 RhI/DPEphos/TFA 作为催化体系，脂肪族和芳香族内部甲基取代的炔烃作为合适的底物，以良好到优异的产率区域选择性地产生有价值的支链 α-烯丙基化 1,3-二羰基化合物。一个简单的基本皂化-脱羧程序提供了获得有价值的 γ,δ-不饱和酮的途径。该反应显示出广泛的官能团耐受性，并且两个反应伙伴的众多结构变化突出了该方法的合成潜力和灵活性。
• A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans
  作者：Roberto Antonioletti、Paolo Bovicelli、Savina Malancona

  DOI：10.1016/s0040-4020(01)01173-5

  日期：2002.1

  A two step synthetic strategy for obtaining 2-alkenyl-1,3-dicarbonyl compounds from the corresponding 1,3-dicarbonyl compounds is reported. The method is based on a Knoevenagel condensation and a Michael addition using a high order organocuprate procedure, and proves to be of general value, Obtained compounds are useful starting materials for the synthesis of furan derivatives, (C) 2002 Elsevier Science Ltd. All rights reserved.
• Iodoenolcyclization of 2-Allyl Substituted b-Keto Esters under Thermodynamic Conditions
  作者：Roberto Antonioletti、Savina Malancona、Paolo Bovicelli

  DOI：10.3987/com-04-10081

  日期：——

  An improved procedure for the synthesis of diastereo-enriched tetrasubstituted 4,5-dihydrofurans by using I-2-induced enolcyclization of beta-keto esters is reported. The reactions using I-2 in anhydrous MeCN are considered under thermodynamic control and the more stable trans isomers are preferentially produced.