ethyl 3-hydroxy-5-methylhex-4-enoate | 126416-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 3-hydroxy-5-methylhex-4-enoate
• 英文别名: 3-hydroxy-5-methyl-hex-4-enoic acid ethyl ester；3-Hydroxy-5-methyl-hex-4-ensaeure-aethylester
• CAS: 126416-16-8
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: DIUVRMCAJBVTPS-UHFFFAOYSA-N

物化性质

• 沸点：
  253.1±20.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-5-methylhex-4-enoate 在 lithium aluminium tetrahydride 作用下， 生成 5,5-dimethyl-4-pentene-1,3-diol
  参考文献：
  名称：

  具有1,2,4-三恶烷结构的双环过氧化物和原酸酯。

  摘要：

  DOI：

  10.1002/anie.200701397
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 乙酸乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 ethyl 3-hydroxy-5-methylhex-4-enoate
  参考文献：
  名称：

  The substrate scope of dehydratases in antibiotic biosynthesis and their application in kinetic resolutions

  摘要：

  从硼菌素生物合成中发现的脱水酶BorDH2在3D醇的脱水中具有广泛的底物耐受性，并应用于动力学分辨率中。

  DOI：

  10.1039/d2ob01879a

文献信息

• Fischer; Loewenberg, Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 283
  作者：Fischer、Loewenberg

  DOI：——

  日期：——
• Reformatsky Reaction in Water:  Evidence for a Radical Chain Process
  作者：Lothar W. Bieber、Ivani Malvestiti、Elisabeth C. Storch

  DOI：10.1021/jo970827k

  日期：1997.12.1

  The Reformatsky reaction of 2-bromo esters and carbonyl compounds in the presence of zinc can be carried out in concentrated aqueous salt solutions without any cosolvent. The reaction of bromoacetates is greatly enhanced by catalytic amounts of benzoyl peroxide or peracids and gives satisfactory yields with aromatic aldehydes. Preparative yields comparable to those of the traditional procedure are obtained with ethyl 2-bromoisobutyrate. This ester needs no catalyst and reacts even with saturated aldehydes and aromatic ketones, although in law yields. A radical chain mechanism, initiated by electron abstraction from the organometallic Reformatsky reagent, is proposed. Two nonchain pathways, involving radicals directly produced od the metal surface, may compete, especially in the case of secondary and tertiary halides.
• Bortolussi, Michel; Seyden-Penne, Jacqueline, Synthetic Communications, 1989, vol. 19, # 13-14, p. 2355 - 2362
  作者：Bortolussi, Michel、Seyden-Penne, Jacqueline

  DOI：——

  日期：——
• Antimalarial Peroxide Dyads from Natural Artemisinin and Hydroxyalkylated 1,2,4-Trioxanes
  作者：Axel G. Griesbeck、Jörg Neudörfl、Achim Hörauf、Sabine Specht、Angela Raabe

  DOI：10.1021/jm9002523

  日期：2009.5.28

  Three synthetic approaches to highly antimalarial peroxide dyads that are composed of the natural artemisinin part (either as dihydroartemisinin or artesunic acid components) and synthetic 1,2,4-trioxanes linked by ether or ester bridges are described. Photooxygenation is the key step to introduce the trioxane group initially or at the end of the reaction sequence, respectively. Dihydroartemisinin or artesunate coupling to hydroxyethyltrioxanes are the two processes that use intact peroxide units from the beginning, whereas the dihydroartemisinin-coupling to an allylic alcohol is a postphotooxygenation route, where the second trioxane ring is installed in the last step of the procedure.