ethyl (Z)-3-(furan-2-yl)but-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 (Z)-3-(furan-2-yl)but-2-enoate
• 英文别名: ethyl 3-(2-furanyl)-2-butenoate
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: YYBVPARBUHYQJD-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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 (Z)-3-(furan-2-yl)but-2-enoate 、 Γ-十八碳三烯酸 在 高氯酸 、 三氟乙酸酐 作用下， 生成 ether 3-[5-(1-oxo-9,12,15-octadecatrienyl)-2-furanyl]-2-butenoate
  参考文献：
  名称：

  Acylated furanyl and thienyl acrylic acids

  摘要：

  这项发明涉及到酰化呋喃丙烯酸、盐、酯和酰胺，酰化噻吩基丙烯酸、盐、酯和酰胺，以及它们作为降脂药剂的用途，以及生产这些化合物的过程。

  公开号：

  US04335098A1
• 作为产物：
  描述：

  2-呋喃乙醛 在 sodium hydride 、 维生素 B2 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 49.0h， 生成 ethyl (Z)-3-(furan-2-yl)but-2-enoate
  参考文献：
  名称：

  A Bio-Inspired, CatalyticE→ZIsomerization of Activated Olefins

  摘要：

  Herein, Nature's flavin-mediated activation of complex (poly)enes has been translated to a small molecule paradigm culminating in a highly (Z)-selective, catalytic isomerization of activated olefins using (-)-ribo-flavin (up to 99:1 Z/E). In contrast to the prominent Z -> E isomerization of the natural system, it was possible to invert the directionality of the isomerization (E -> Z) by simultaneously truncating the retinal scaffold, and introducing a third olefin substituent to augment A1,3-strain upon isomerization. Consequently, conjugation is reduced in the product chromophore leading to a substrate/product combination with discrete photophysical signatures. The operationally simple isomerization protocol has been applied to a variety of enone-derived substrates and showcased in the preparation of the medically relevant 4-substituted coumarin scaffold. A correlation of sensitizer triplet energy (ET) and reaction efficiency, together with the study of additive effects and mechanistic probes, is consistent with a triplet energy transfer mechanism.

  DOI：

  10.1021/jacs.5b07136

文献信息

• Acylated furanyl and thienyl acrylic acids, process for their production, and pharmaceutical compositions
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0046595A1

  公开（公告）日：1982-03-03

  This invention relates to acylated furanyl acrylic acids, salts, esters and amides, to acylated thienyl acrylic acids, salts, esters and amides, and to the process for producing said compounds. Furthermore, the invention relates to pharmaceutical compositions having hypolipidemic activity, which contain such compounds.

  本发明涉及酰化呋喃丙烯酸、盐、酯和酰胺，涉及酰化噻吩丙烯酸、盐、酯和酰胺，以及生产上述化合物的工艺。此外，本发明还涉及含有此类化合物的具有降血脂活性的药物组合物。
• US4335098A
  申请人：——

  公开号：US4335098A

  公开（公告）日：1982-06-15
• A Bio-Inspired, Catalytic<i>E</i>→<i>Z</i>Isomerization of Activated Olefins
  作者：Jan B. Metternich、Ryan Gilmour

  DOI：10.1021/jacs.5b07136

  日期：2015.9.9

  Herein, Nature's flavin-mediated activation of complex (poly)enes has been translated to a small molecule paradigm culminating in a highly (Z)-selective, catalytic isomerization of activated olefins using (-)-ribo-flavin (up to 99:1 Z/E). In contrast to the prominent Z -> E isomerization of the natural system, it was possible to invert the directionality of the isomerization (E -> Z) by simultaneously truncating the retinal scaffold, and introducing a third olefin substituent to augment A1,3-strain upon isomerization. Consequently, conjugation is reduced in the product chromophore leading to a substrate/product combination with discrete photophysical signatures. The operationally simple isomerization protocol has been applied to a variety of enone-derived substrates and showcased in the preparation of the medically relevant 4-substituted coumarin scaffold. A correlation of sensitizer triplet energy (ET) and reaction efficiency, together with the study of additive effects and mechanistic probes, is consistent with a triplet energy transfer mechanism.
• Acylated furanyl and thienyl acrylic acids
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04335098A1

  公开（公告）日：1982-06-15

  This invention relates to acylated furanyl acrylic acids, salts, esters and amides, to acylated thienyl acrylic acids, salts, esters and amides, and to their use as hypolipidemic agents, and to the processes for producing said compounds.

  这项发明涉及到酰化呋喃丙烯酸、盐、酯和酰胺，酰化噻吩基丙烯酸、盐、酯和酰胺，以及它们作为降脂药剂的用途，以及生产这些化合物的过程。