ethyl 2-ethylfuran-3-carboxylate | 83004-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 2-ethylfuran-3-carboxylate
• 英文别名: ethyl 2-ethyl-3-furoate；Ethyl 2-ethyl-3-furancarboxylate
• CAS: 83004-20-0
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: IAMVSJNWMRPQLA-UHFFFAOYSA-N

物化性质

• 沸点：
  234.5±28.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-ethylfuran-3-carboxylate 在 三乙胺 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 20.17h， 生成 benzoic 2-ethyl-3-furoic anhydride
  参考文献：
  名称：

  Syntheses and Pyrolyses of Furan Analogues of α-Oxo-o-quinodimethanes. Formation of Methylenecyclobutenone and 1-Buten-3-yne via a Vinylcarbene–Cyclopropene Rearrangement

  摘要：

  Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3-methyl-2-furoic anhydride (13) at 550 degrees C and ca. 10(-2) Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of alpha-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective carbenes 34 and 36 is proposed. Carbenes 34 and 36 are interconvertible via a cyclopropene intermediate 35. A ring contraction from 36 will give 16, whereas a ring-opening of 34 followed by elimination of a CO molecule then leads to 17. The proposed mechanism is supported by substituent- and deuterium-labeling study on FVP of the derivatives of 12.

  DOI：

  10.1021/jo201743h
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 反应 4.17h， 生成 ethyl 2-ethylfuran-3-carboxylate
  参考文献：
  名称：

  Syntheses and Pyrolyses of Furan Analogues of α-Oxo-o-quinodimethanes. Formation of Methylenecyclobutenone and 1-Buten-3-yne via a Vinylcarbene–Cyclopropene Rearrangement

  摘要：

  Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3-methyl-2-furoic anhydride (13) at 550 degrees C and ca. 10(-2) Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of alpha-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective carbenes 34 and 36 is proposed. Carbenes 34 and 36 are interconvertible via a cyclopropene intermediate 35. A ring contraction from 36 will give 16, whereas a ring-opening of 34 followed by elimination of a CO molecule then leads to 17. The proposed mechanism is supported by substituent- and deuterium-labeling study on FVP of the derivatives of 12.

  DOI：

  10.1021/jo201743h

文献信息

• Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate
  作者：Eloi P Coutant、Vincent Hervin、Glwadys Gagnot、Candice Ford、Racha Baatallah、Yves L Janin

  DOI：10.3762/bjoc.14.264

  日期：——

  We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered

  我们在这里探索了基于古老的丙二酸二乙酯对α-氨基酯的接触范围，该方法涉及丙二酸二乙酯在醛上的Knoevenagel缩合反应，所得亚烷基丙二酸酯的还原，相应α-羟基亚氨基酯的制备及其最终还原。尽管遇到了一些意想不到的限制，但这种合成途径被证明是通用的。在进行肟化步骤之前，使用Suzuki-Miyaura偶联或环加成法对某些中间体进行了合成修饰，从而获得了更多的α-氨基酯。此外，探索了其他通往α-羟基亚氨基酯的途径，包括试图改善乙基β-溴-α-羟基亚氨基羧酸酯与各种烷基呋喃化合物之间的环加成反应。
• Pratesi; Villa; Ferri, Farmaco, Edizione Scientifica, 1982, vol. 37, # 6, p. 398 - 410
  作者：Pratesi、Villa、Ferri、De Micheli、Grana、Santagostino Barbone、Silipo、Vittoria

  DOI：——

  日期：——
• PRATESI, P.;VILLA, L.;FERRI, V.;DE, MICHELI, C.;GRANA, E.;SANTAGOSTINO, B+, FARMACO. ED. SCI., 1982, 37, N 6, 398-410
  作者：PRATESI, P.、VILLA, L.、FERRI, V.、DE, MICHELI, C.、GRANA, E.、SANTAGOSTINO, B+

  DOI：——

  日期：——
• PHOSPHORYLAMIDES, THEIR PREPARATION AND USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0852498A1

  公开（公告）日：1998-07-15
• [EN] PHOSPHORYLAMIDES, THEIR PREPARATION AND USE<br/>[FR] PHOSPHORYLAMIDES, LEUR PREPARATION ET LEUR UTILISATION
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：WO1997011705A1

  公开（公告）日：1997-04-03

  (EN) A phosphorylamide derivative represented by general formula (I), wherein R represents an amino group that may be substituted, or a salt thereof, possesses potent antibacterial activity against $i(Helicobacter) bacterium, especially $i(Helicobacter pylori), and is useful for prevention or treatment of digestive diseases caused by $i(Helicobacter) bacterium, solely or in combination with an antacid or an acid secretion inhibitor.(FR) L'invention concerne un dérivé de phosphorylamide représenté par la formule générale (I), dans laquelle R représente un groupe amino qui peut être substitué, ou un sel de ce dérivé. Ledit dérivé présente une puissante activité antibactérienne contre la bactérie Helicobacter, en particulier Helicobacter pylori, et il est utile pour la prévention ou le traitement de maladies du système digestif causées par la bactérie Helicobacter, seul ou combiné à un antiacide ou à un inhibiteur de sécrétions acides.