2-methoxyacrolein | 18218-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxyacrolein
• 英文别名: 2-methoxypropenal；α-methoxyacrolein；2-Propenal, 2-methoxy-；2-methoxyprop-2-enal
• CAS: 18218-93-4
• 化学式: C₄H₆O₂
• 分子量: 86.0904
• InChiKey: BNBWSNNWJPEFDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxyacrolein 在 盐酸 、 对苯二酚 作用下， 以 水 、 乙腈 为溶剂， 反应 0.83h， 生成 丙酮醛
  参考文献：
  名称：

  2-alkoxypropenals as synthetic equivalents of methylglyoxal in the synthesis of heterocycles

  摘要：

  One-pot synthesis of 2-methylquinoxaline, 3-hydroxy-2-methylimidazo[1,2-a]pyridine, and 2-methyl-3,7-dihydroimidazo[1,2-a]pyrazin-3-one via cycloaddition of N,N-binucleophilic o-phenylenediamine, 2-aminopyridine, and 2-aminopyrazine, respectively, to methylglyoxal generated in situ by hydrolysis of 2-alkoxypropenals is reported for the first time. Thus 2-alkoxypropenals in weakly acidic medium (25-80A degrees C, 1-4 h) are convenient synthetic equivalents of methylglyoxal in the synthesis of heterocyclic compounds.

  DOI：

  10.1134/s1070428013030196
• 作为产物：
  描述：

  2,3-di-O-methyl-DL-glyceraldehyde 生成 2-methoxyacrolein
  参考文献：
  名称：

  PETRUSOVA-POLAKOVA, M.;FEDORONKO, M.

  摘要：

  DOI：

文献信息

• PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH INSECTICIDAL ACTIVITIES
  申请人：Li Zhong

  公开号：US20090111847A1

  公开（公告）日：2009-04-30

  The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhopper, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus , carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.

  本发明公开了一种亚硝基甲烯衍生物，以及它们的制备方法和用途。杀虫活性测试表明，本发明的亚硝基甲烯衍生物不仅对具有刺吸型或擦伤型口器的昆虫（如蚜虫、叶蝉、植食蝗、蓟马和烟粉虱及其抗性品系）表现出高杀虫活性，而且对水稻纵卷叶象、胭脂蜘蛛螨等也表现出高杀虫活性，它们还可用于预防卫生害虫和白蚁。
• Process for preparing substituted chroman derivatives
  申请人：BASF Aktiengesellschaft

  公开号：US06136986A1

  公开（公告）日：2000-10-24

  The invention relates to a process for preparing substituted chroman derivatives of the general formula VII, ##STR1## where X is the group --CN, --COOR.sup.3, --CHO, --CH.sub.2 OR.sup.7 or --CH(OR.sup.8).sub.2, R.sup.2 is a C.sub.1 -C.sub.23 -alkyl, C.sub.2 -C.sub.23 -alkenyl, C.sub.6 -C.sub.18 -aryl or C.sub.7 -C.sub.18 -aralkyl radical, R.sup.3 is hydrogen or an optionally substituted C.sub.1 -C.sub.4 -alkyl radical, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, hydrogen or a C.sub.1 -C.sub.4 -alkyl radical, R.sup.7 is hydrogen or a C.sub.1 -C.sub.4 -alkyl radical, R.sup.8 is a C.sub.1 -C.sub.4 -alkyl radical, or the two radicals are a C.sub.2 -C.sub.6 -alkylene radical which links the two oxygen atoms to form a cyclic acetal and is optionally branched or may carry one or two carboxyl groups, cyclohexyl or phenyl radicals, and to the novel intermediates of the process.

  该发明涉及制备通式VII的取代色苷衍生物的过程，其中X是基团--CN，--COOR.sup.3，--CHO，--CH.sub.2 OR.sup.7或--CH(OR.sup.8).sub.2，R.sup.2是C.sub.1-C.sub.23-烷基，C.sub.2-C.sub.23-烯基，C.sub.6-C.sub.18-芳基或C.sub.7-C.sub.18-芳基烷基基团，R.sup.3是氢或可选择取代的C.sub.1-C.sub.4-烷基基团，R.sup.4，R.sup.5，R.sup.6是独立的氢或C.sub.1-C.sub.4-烷基基团，R.sup.7是氢或C.sub.1-C.sub.4-烷基基团，R.sup.8是C.sub.1-C.sub.4-烷基基团，或两个基团是将两个氧原子连接起来形成环状缩醛的C.sub.2-C.sub.6-烷基基团，可选择支链或带有一个或两个羧基，环己基或苯基基团，并涉及该过程的新中间体。
• Reaction of 2-Alkoxypropenals with α-Hydroxyamino Oximes and 1,2-Bis(hydroxyamino)cyclohexane
  作者：N. A. Keiko、E. A. Funtikova、L. I. Larina、G. I. Sarapulova、D. G. Mazhukin、T. V. Rybalova、A. Ya. Tikhonov

  DOI：10.1007/s11178-005-0361-1

  日期：2005.10

  Reactions of 2-alkoxypropenals with α-hydroxyamino oximes in neutral medium involve the aldehyde group of the former to afford both acyclic and cyclic azomethine oxides: N-(2-hydroxyiminoalkyl)-N-(2-alkoxy-2-propenylidene)amine oxides and 1-hydroxy-2,5-dihydroimidazole 3-oxides. The state of tautomeric equilibrium between the cyclic and acyclic products depends on the solvent nature and temperature. The reaction in acidic aqueous medium is accompanied by hydrolysis of the vinyl ether moiety in 2-alkoxy-propenals with formation of 2-oxopropionaldehyde which reacts with α-hydroxyamino oxime at the hydroxy-amino group to give substituted pyrazine 1,4-dioxides. The reaction of 2-alkoxypropenals with 1,2-bis-(hydroxyamino)cyclohexane leads to formation of 2-(1-alkoxyvinyl)-1,3-dihydroxyperhydrobenzimidazoles. The structure of the products was proved by IR, UV, and 1H and 13C NMR spectroscopy and X-ray analysis.

  2-烷氧丙烯醛与α-羟基氨基肟在中性介质中的反应涉及前者的醛基，生成无环和环状的亚胺氧化物：N-(2-羟基亚胺烷基)-N-(2-烷氧基-2-丙烯基)胺氧化物和1-羟基-2,5-二氢咪唑-3-氧化物。环状和无环产物之间的并置平衡状态取决于溶剂的性质和温度。在酸性水相中反应伴随着2-烷氧基丙烯醛中乙烯醚部分的水解，形成2-氧丙醛，该醛与α-羟基氨基肟在羟基氨基组上反应，生成取代的吡嗪1,4-二氧化物。2-烷氧丙烯醛与1,2-双(羟基氨基)环己烷的反应生成2-(1-烷氧基乙烯基)-1,3-二羟基全氟苯并咪唑。产品的结构通过红外光谱、紫外光谱、1H和13C核磁共振光谱以及X射线分析得到了验证。
• Acid-catalyzed hydrolysis of 2-methoxypropenal
  作者：Michal Fedoroňko、Mária Petrušová、Igor Tvaroška

  DOI：10.1016/0008-6215(83)88137-3

  日期：1983.4

  undergoes general acid-catalyzed hydrolysis with formation of 2-oxopropanal. The kinetics of this reaction were studied, the rate constants established, and a reaction mechanism is suggested. Hydrolysis of 2-methoxypropenal is governed by a mechanism of the vinyl ether type, and the presence of the aldehyde group causes a decrease in the reaction rate. The analogy of the acid-catalyzed hydrolysis of 2-methoxypropenal

  摘要酸性介质中的2-甲氧基丙醛经过一般的酸催化水解，生成2-氧杂丙醛。研究了该反应的动力学，确定了速率常数，并提出了反应机理。2-甲氧基丙烯醛的水解受乙烯基醚类型的机理支配，并且醛基的存在导致反应速率降低。溶剂同位素效应kD / kH = 0.41，布朗斯台德指数α= 0.60，表明了2-甲氧基丙烯醛与乙烯基醚的酸催化水解反应的相似性。所发现的活化参数以及2-甲氧基丙烯和其他模型化合物中电荷分布的量子化学计算也用于解释标题化合物酸催化水解的机理。
• Reactions of alcohols with α-alkoxyacroleins at room temperature
  作者：N. A. Keiko、Yu. A. Chuvashev、L. G. Stepanova、M. G. Voronkov

  DOI：10.1007/bf02641546

  日期：1998.12

  medium at 20°C under kinetically controlled conditions is the Markovnikoff addition at the C=C bond to form 2,2-dialkoxypropanals (methylglyoxal ketals). Under conditions of thermodynamic control, subsequent acetalization of the aldehyde group occurs to form 1,1,2,2-tetraalkoxypropanes. When the duration of the reaction is further increased in the absence of a water acceptor, the ketal group undegroes hydrolysis

  醇与 α-烷氧基丙烯醛在酸性介质中在动力学控制条件下于 20°C 反应的第一阶段是在 C=C 键上进行马尔可夫尼科夫加成以形成 2,2-二烷氧基丙醛（甲基乙二醛缩酮）。在热力学控制条件下，醛基随后发生缩醛化以形成 1,1,2,2-四烷氧基丙烷。当在不存在水受体的情况下进一步增加反应持续时间时，缩酮基团不进行水解并形成甲基乙二醛缩醛。开发了一种制备甲基乙二醛缩酮的方法。