(E)-ethyl 3-methoxy-2-hexenoate | 112857-49-5

• 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: (E)-ethyl 3-methoxy-2-hexenoate
• 英文别名: Ethyl 3-methoxy-2(E)-hexenoate；ethyl (E)-3-methoxyhex-2-enoate
• CAS: 112857-49-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: XFTGRSYJDWOSLG-BQYQJAHWSA-N

物化性质

• 沸点：
  229.5±23.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-methoxy-2-hexenoate 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 生成 (E,2S,S_S)-1-(p-tolylsulfinyl)-4-methoxy-3-heptene-2-ol
  参考文献：
  名称：

  New insights into the reduction of β,δ-diketo-sulfoxides

  摘要：

  New developments in the reduction of beta,delta-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the beta-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the delta-position) as the major one. We propose a rationale to explain the side reactions occurring during the reduction of unprotected beta,delta-diketo-sulfoxides and showed that judicious protection of the delta-carbonyl group gave all diastereoisomers of beta-hydroxy-delta-ketosulfoxides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00125-3
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 硫酸 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 以95.8%的产率得到(E)-ethyl 3-methoxy-2-hexenoate
  参考文献：
  名称：

  5-arylalkyl-4-alkoxy-2(5H)-furanones, intermediates and processes for

  摘要：

  本发明提供了式子为：##STR1## 的5-芳基烷基-4-烷氧基-2(5H)-呋喃酮，其中C-5和C-.alpha.上的氧原子相对于彼此处于threo位，但不包括当n=0或2时，R.sup.2为H或CH.sub.3，R.sup.o=H，R.sup.1=CH.sub.3，R.sup.3=H和R.sup.4=H的化合物。本发明还提供了制备它们的方法，以及新的3-烷氧基-5-(取代基)苯基-2(E)，4(E)-戊二烯酸酯作为制备新呋喃酮衍生物的反应中间体。threo系列的新呋喃酮衍生物作为抗惊厥/抗癫痫药物具有活性。因此，本发明还提供了含有这些新呋喃酮衍生物的药物，以及已知的呋喃酮，其抗惊厥/抗癫痫药效首次被发现。

  公开号：

  US04855320A1

文献信息

• 5-Arylalkyl-4-alkoxy-2(5H)-furanone, Zwischenprodukte und Verfahren zu ihrer Herstellung sowie ihre Anwendung als therapeutische Wirkstoffe
  申请人：Dr. Willmar Schwabe GmbH & Co.

  公开号：EP0247320B1

  公开（公告）日：1990-12-27
• US4855320A
  申请人：——

  公开号：US4855320A

  公开（公告）日：1989-08-08
• New insights into the reduction of β,δ-diketo-sulfoxides
  作者：Gilles Hanquet、Xavier J. Salom-Roig、Laurence Gressot-Kempf、Steve Lanners、Guy Solladié

  DOI：10.1016/s0957-4166(03)00125-3

  日期：2003.5

  New developments in the reduction of beta,delta-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the beta-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the delta-position) as the major one. We propose a rationale to explain the side reactions occurring during the reduction of unprotected beta,delta-diketo-sulfoxides and showed that judicious protection of the delta-carbonyl group gave all diastereoisomers of beta-hydroxy-delta-ketosulfoxides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 5-arylalkyl-4-alkoxy-2(5H)-furanones, intermediates and processes for
  申请人：Dr. Willmar Schwabe GmbH & Company

  公开号：US04855320A1

  公开（公告）日：1989-08-08

  The present invention provides 5-arylalkyl-4-alkoxy-2(5H)-furanones of the formula: ##STR1## wherein the oxygen atoms on C-5 and C-.alpha., relative to one another, are in the threo-position, with the exclusion of those compounds of the formula (I) wherein R.sup.2 is H or CH.sub.3 when n=0 or 2, R.sup.o =H, R.sup.1 =CH.sub.3, R.sup.3 =H and R.sup.4 =H. The present invention also provides processes for their preparation, as well as new 3-alkoxy-5-(subst.)-phenyl-2(E), 4(E)-pentadienoates as reactive intermediates for the preparation of the new furanone derivatives. The new furanone derivatives of the threo series are active as anticonvulsives/anti-epileptics. Therefore, the present invention also provides medicaments which contain these new furanone derivatives, as well as known furanones, the anticonvulsive/anti-epileptic effectiveness of which has been found for the first time.

  本发明提供了式子为：##STR1## 的5-芳基烷基-4-烷氧基-2(5H)-呋喃酮，其中C-5和C-.alpha.上的氧原子相对于彼此处于threo位，但不包括当n=0或2时，R.sup.2为H或CH.sub.3，R.sup.o=H，R.sup.1=CH.sub.3，R.sup.3=H和R.sup.4=H的化合物。本发明还提供了制备它们的方法，以及新的3-烷氧基-5-(取代基)苯基-2(E)，4(E)-戊二烯酸酯作为制备新呋喃酮衍生物的反应中间体。threo系列的新呋喃酮衍生物作为抗惊厥/抗癫痫药物具有活性。因此，本发明还提供了含有这些新呋喃酮衍生物的药物，以及已知的呋喃酮，其抗惊厥/抗癫痫药效首次被发现。