ethyl 3-methyl-3-(2-furyl)-2-propenoate | 59562-22-0

• 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 3-methyl-3-(2-furyl)-2-propenoate
• 英文别名: ethyl (E)-3-(furan-2-yl)but-2-enoate
• CAS: 59562-22-0
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: YYBVPARBUHYQJD-BQYQJAHWSA-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 3-methyl-3-(2-furyl)-2-propenoate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以71.4%的产率得到ethyl 4-bromo-3-(2-furyl)-2-butenoate
  参考文献：
  名称：

  Spirkova, Katarina; Kovac, Jaroslav; Konecny, Vaclav, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 1, p. 142 - 149

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (2E)-3-(furan-2-yl)acrylate 以 乙醚 为溶剂， 反应 0.5h， 生成 ethyl 3-methyl-3-(2-furyl)-2-propenoate
  参考文献：
  名称：

  Spirkova, Katarina; Kovac, Jaroslav; Konecny, Vaclav, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 1, p. 142 - 149

  摘要：

  DOI：

文献信息

• Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers
  作者：Jae Hun Sim、Choong Eui Song

  DOI：10.1002/anie.201611466

  日期：2017.2.6

  new catalytic reactions for otherwise unreactive substrate systems. Under the “on water” reaction conditions, extremely unreactive β,β‐disubstituted nitroalkenes smoothly underwent enantioselective Michael addition reactions with dithiomalonates using a chiral squaramide catalyst, affording both enantiomers of highly enantioenriched Michael adducts with all‐carbon‐substituted quaternary centers. The

  水可以使原本没有反应的底物系统发生新的催化反应。在“水上”反应条件下，极度不活泼的β，β-二取代硝基烯烃通过手性方酰胺催化剂与二硫代丙二酸酯平稳地进行对映选择性Michael加成反应，提供了具有全碳取代的季中心的高度对映体丰富的Michael加合物的对映异构体。已开发的“在水上”方案已成功应用于手性GABA类似物的可扩展的一锅合成，该手性GABA类似物在β位置具有全碳四元立体异构中心，这可能显示出非常有趣的药物特性。
• Nickel-catalyzed cross-coupling of β-carbonyl alkenyl pivalates with arylzinc chlorides
  作者：Wen-Jing Pan、Zhong-Xia Wang

  DOI：10.1039/c7ob02947k

  日期：——

  The nickel-catalyzed cross-coupling reaction of β-carbonyl alkenyl pivalates with arylzinc reagents generates 3-aryl-substituted α,β-unsaturated carbonyl compounds via C–O bond cleavage. The reaction features mild reaction conditions, a wide scope of substrates, and good functional group tolerance.

  镍催化的β-羰基链烯基新戊酸酯与芳基锌试剂的交叉偶联反应可通过C–O键裂解生成3-芳基取代的α，β-不饱和羰基化合物。该反应具有温和的反应条件，广泛的底物范围和良好的官能团耐受性。
• 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。
• ——
  作者：

  DOI：——

  日期：——
• 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.