ethyl (E)-3-(5-hydroxymethylfuran-2-yl)-prop-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-3-(5-hydroxymethylfuran-2-yl)-prop-2-enoate
• 英文别名: ethyl (E)-3-[5-(hydroxymethyl)furan-2-yl]prop-2-enoate
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: ASSLJVOYLPMDES-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-羟甲基糠醛 、 磷酰基乙酸三乙酯 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.3h， 以90%的产率得到ethyl (E)-3-(5-hydroxymethylfuran-2-yl)-prop-2-enoate
  参考文献：
  名称：

  Mouloungui, Zephirin; Delmas, Michel; Gaset, Antoine, Synthetic Communications, 1984, vol. 14, # 8, p. 701 - 706

  摘要：

  DOI：

文献信息

• One-Pot, Fluoride-Promoted Wittig Reaction
  作者：Tiziano Fumagalli、Guido Sello、Fulvia Orsini

  DOI：10.1080/00397910802654633

  日期：2009.5.22

  ethyl α-bromoacetate with aliphatic, aromatic, and heteroaromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced α,β-unsaturated esters in good to excellent yields and E-stereoselectivity. Under the same conditions, reactions of ethyl α-bromopropionate, α-bromo acetonitrile, and α-bromoacetophenone with aliphatic and aromatic aldehydes in the presence of tri-n-butylphosphine

  摘要 开发了一种一锅法、氟化物促进的 Wittig 反应。在三正丁基膦和四丁基氟化铵的存在下，α-溴乙酸乙酯与脂肪族、芳香族和杂芳香族醛的反应产生了 α,β-不饱和酯，收率和 E-立体选择性都非常好。在相同条件下，α-溴丙酸乙酯、α-溴乙腈和 α-溴苯乙酮与脂肪族和芳香族醛在三正丁基膦和四丁基氟化铵的存在下反应，在良好的 E 中产生了预期的 α,β-不饱和衍生物-立体选择性。该协议扩展到半稳定叶立德并应用于一些考布他汀类似物的合成。
• MOULOUNGUL, Z.;DELMAS, M.;GASET, A., SYNTH. COMMUN., 1984, 14, N 8, 701-705
  作者：MOULOUNGUL, Z.、DELMAS, M.、GASET, A.

  DOI：——

  日期：——
• PRODUCTION AND USE OF FURAN COMPOUNDS
  申请人：Coöperatie Koninklijke Cosun U.A.

  公开号：US20200123122A1

  公开（公告）日：2020-04-23

  The present invention, relates to processes for the production and conversion of furan compounds. In certain embodiments the invention concerns the conversion of furfural compounds into a so-called Knoevenagel products and for the further conversion of such Knoevenagel products into furan commodities. The reactions involved, generally speaking, use benign chemicals and conditions and have good yields and selectivity, and it is expected that they can be implemented on a large (industrial) scale in an economically feasible manner. Also, with the processes developed by the present inventors, various highly interesting new furan commodities become available. The invention also provides various intermediate and end-products obtained with the processes of the invention.