diethyl 2,3-dimethoxybenzylidenemalonate | 39059-74-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: diethyl 2,3-dimethoxybenzylidenemalonate
• 英文别名: Diethyl(2,3-dimethoxybenzylidene)propanedioate；diethyl 2-[(2,3-dimethoxyphenyl)methylidene]propanedioate
• CAS: 39059-74-0
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: VCHSRJSLOQLZKE-UHFFFAOYSA-N

物化性质

• 沸点：
  381.3±37.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  diethyl 2,3-dimethoxybenzylidenemalonate 以96%的产率得到
  参考文献：
  名称：

  SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;HIRATA, TAKEO;MAKI, YOSHITAKA;KAWAMATSU+, CHEM. AND PHARM. BULL., 1983, 31, N 2, 560-569

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl malonate 、 2,3-二甲氧基苯甲醛 在 哌啶 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以85.5%的产率得到diethyl 2,3-dimethoxybenzylidenemalonate
  参考文献：
  名称：

  Antiulcer activity of 5-benzylthiazolidine-2,4-dione derivatives.

  摘要：

  制备了5-苄基-噻唑烷-2,4-二酮衍生物，并通过结扎大鼠幽门和水浸应激大鼠模型进行了抗分泌和抗溃疡活性的检验。其中一些化合物，尤其是5-(2, 4, 5-三丙氧基苄基)噻唑烷-2, 4-二酮（4）和5-(2, 4-二甲氧基苄基)噻唑烷-2, 4-二酮（23），表现出显著的药理活性。结构-活性关系在此进行了讨论。

  DOI：

  10.1248/cpb.31.560

文献信息

• Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation
  作者：Jitendra R Harjani、Susheel J Nara、Manikrao M Salunkhe

  DOI：10.1016/s0040-4039(01)02341-3

  日期：2002.2

  [bpy]Cl·AlCl3, N=0.67 ionic liquids were found to work well as the Lewis acid catalyst and solvent in the Knoevenagel condensations of benzaldehyde and substituted benzaldehydes with diethyl malonate to give benzylidene malonates. The benzylidene malonates subsequently underwent Michael additions with diethyl malonate. The extent of Michael product formed during the reaction was found to vary with the Lewis acidity

  1-丁基-3-甲基咪唑鎓氯铝酸盐，[bmim] Cl·AlCl 3，N = 0.67和1-丁基吡啶鎓氯铝酸盐，[bpy] Cl·AlCl 3，N发现＝ 0.67离子液体在苯甲醛和取代的苯甲醛与丙二酸二乙酯的Knoevenagel缩合反应中作为路易斯酸催化剂和溶剂很好地工作，得到亚苄基丙二酸酯。亚苄基丙二酸酯随后与丙二酸二乙酯进行迈克尔加成。发现反应过程中迈克尔产物的形成程度随路易斯酸度和离子液体的摩尔比而变化。证明了离子液体的路易斯酸度对Knoevenagel和Michael产品的影响。在2-羟基芳基醛的情况下，该反应导致在环境条件下形成3-乙氧基羰基香豆素。
• Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones
  作者：Xianran He、Guanpeng Qiu、Jin Yang、Yuling Xiao、Zhongyuan Wu、Guofu Qiu、Xianming Hu

  DOI：10.1016/j.ejmech.2010.05.034

  日期：2010.9

  In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Their neurotoxicity was determined by the rotorod test. In this series, all of the alkyl- and aryl-substituted 5,5-cyclo-propanespirohydantoins showed more or less protection against MES and/or scPTZ models. The most active of the series was 6-methyl-1-(4-(methylsulfonyl)phenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (6t), which showed a MES ED50 value of 12.5 mg/kg in mice. The median toxic dose (TD50) was 310 mg/kg, providing compound 6t with a protection index (PI = TD50/ED50) of 24.8 in the MES test which is better than phenytoin. (C) 2010 Elsevier Masson SAS. All rights reserved.
• A one-pot synthesis of coumarins from dipotassium O-methoxybenzylidenemalonates
  作者：Osmo E. O. Hormi、Carita Peltonen、Riitta Bergström (née Moisio)

  DOI：10.1039/p19910000219

  日期：——

  o-Methoxybenzylidenemalonates 1, which are available from o-methoxybenzaldehydes and diethyl malonate, were hydrolysed to the dipotassium malonates 2. Treatment of the salts 2 with trifluoroacetic acid-trifluoroacetic anhydride gave the title coumarins by a demethylative ring-closure reaction in 60-80% yield.
• Antiulcer activity of 5-benzylthiazolidine-2,4-dione derivatives.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、TAKEO HIRATA、YOSHITAKA MAKI、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.31.560

  日期：——

  5-Benzylthiazolidine-2, 4-dione derivatives were prepared and examined for antisecretory and antiulcer activities using pylorus-ligated rats and water-immersion stress rats. Some of these compounds, in particular, 5-(2, 4, 5-tripropoxybenzyl) thiazolidine-2, 4-dione (4) and 5-(2, 4-dimethoxybenzyl) thiazolidine-2, 4-dione (23), exhibited pronounced pharmacological activities. Structure-activity relationships are discussed.

  制备了5-苄基-噻唑烷-2,4-二酮衍生物，并通过结扎大鼠幽门和水浸应激大鼠模型进行了抗分泌和抗溃疡活性的检验。其中一些化合物，尤其是5-(2, 4, 5-三丙氧基苄基)噻唑烷-2, 4-二酮（4）和5-(2, 4-二甲氧基苄基)噻唑烷-2, 4-二酮（23），表现出显著的药理活性。结构-活性关系在此进行了讨论。
• SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;HIRATA, TAKEO;MAKI, YOSHITAKA;KAWAMATSU+, CHEM. AND PHARM. BULL., 1983, 31, N 2, 560-569
  作者：SOHDA, TAKASHI、MIZUNO, KATSUTOSHI、HIRATA, TAKEO、MAKI, YOSHITAKA、KAWAMATSU+

  DOI：——

  日期：——