2-isobutyryl-3-methyl-pent-4-enoic acid ethyl ester | 422270-82-4

• 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-isobutyryl-3-methyl-pent-4-enoic acid ethyl ester
• 英文别名: Ethyl 3-methyl-2-(2-methylpropanoyl)pent-4-enoate；ethyl 3-methyl-2-(2-methylpropanoyl)pent-4-enoate
• CAS: 422270-82-4
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: NYOYPNUXLSYAEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-isobutyryl-3-methyl-pent-4-enoic acid ethyl ester 在 碘 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到trans-3-ethoxycarbonyl-5-iodomethyl-2-isopropyl-4-methyl-4,5-dihydrofuran
  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：

  异丁酰乙酸乙酯 在 哌啶 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 4.08h， 生成 2-isobutyryl-3-methyl-pent-4-enoic acid ethyl 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

• Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds
  作者：Roberto Antonioletti、Savina Malancona、Paolo Bovicelli

  DOI：10.1016/s0040-4020(02)01064-5

  日期：2002.10

  A study of the stereochemical aspects of I-2-induced cyclisation of 2-alkenyl-1,3-dicarbonyl compounds reveals that the iodoenolcyclisation is strictly dependent on the dicarbonyl species and the substituents in the allylic position. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.