methyl p-[N-(2-methoxycarbonylallyl)-N-methylamino]benzoate | 213256-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl p-[N-(2-methoxycarbonylallyl)-N-methylamino]benzoate
• 英文别名: Methyl 4-((2-(methoxycarbonyl)allyl)(methyl)amino)benzoate；methyl 4-[2-methoxycarbonylprop-2-enyl(methyl)amino]benzoate
• CAS: 213256-72-5
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: NNRGDYVLERSNHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl p-[N-(2-methoxycarbonylallyl)-N-methylamino]benzoate 以 甲醇 为溶剂， 生成 methyl 4-[N-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-methylamino]benzoate
  参考文献：
  名称：

  Synthesis and Biological Activity of 7-Oxo Substituted Analogues of 5-Deaza-5,6,7,8-tetrahydrofolic Acid (5-DATHF) and 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF)

  摘要：

  We recently described the syntheses of 12a-c, 4-amino-7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF), and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), in six steps from commercially available p-substituted methyl benzoates in: 20-27% overall yields; Such analogues were tested in vitro against CCRF-CEM leukemia cells and showed that they are completely devoid of any activity, the IC50 being higher than 20 mug/mL for all cases. To clarify if the presence of the carbonyl group in position C7, the distinctive feature of our synthetic. methodology, is the reason for this lack of activity, we have now obtained the 7-oxo substituted analogues of 5-DATHF and DDATHF, 18a-c, in 10-30% overall yield. Testing of 18a-c in vitro against CCRF-CEM leukemia cells revealed that these compounds are totally inactive. A molecular modeling study of 18b inside the active site of the complex El coli GARTFase-5-DATHF-GAR pointed to an electronic repulsion between the atoms of the 7-ore group and the carbonyl group of Arg90 as a possible explanation for the inactivity of 18a-c.

  DOI：

  10.1021/jm990411u
• 作为产物：
  描述：

  2-(羟甲基)丙烯酸甲酯 在 三溴化磷 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 15.0h， 生成 methyl p-[N-(2-methoxycarbonylallyl)-N-methylamino]benzoate
  参考文献：
  名称：

  Synthesis and Biological Activity of 4-Amino-7-oxo-Substituted Analogues of 5-Deaza-5,6,7,8-tetrahydrofolic Acid and 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid

  摘要：

  The 4-amino-7-oxo-substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF) and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF) were synthesized as potential antifolates. Treatment of the alpha,beta-unsaturated esters 11a-c, obtained in one synthetic step from commercially available para-substituted methyl benzoates (9a-c) and methyl 2-(bromomethyl)acrylate (10), with malononitrile in NaOMe/MeOH afforded the corresponding pyridones 12a-c. Formation of the pyrido[2,3-d]pyrimidines 13a-c was accomplished upon treatment of 12a-c with guanidine in methanol. After the hydrolysis of the ester group present in 13a-c, the resulting carboxylic acids 14a-c were treated with diethyl cyanophosphonate in Et3N/ DMF and coupled with L-glutamic acid dimethyl ester to give 15a-c. Finally, the basic hydrolysis of 15a-c yielded the desired 4-amino-7-oxo-substituted analogues 16a-c in 20-27% overall yield. Compounds 16a-c were tested in vitro against CCRF-CEM leukemia cells. The results obtained indicated that our 4-amino-7-oxo analogues are completely devoid of any activity, the IC50 being higher than 20 mu g/mL for all cases except 14c for which a value of 6.7 mu g/mL was obtained. These results seem to indicate that 16a-c are inactive precisely due to the presence of the carbonyl group in position C7, the distinctive feature or our synthetic methodology.

  DOI：

  10.1021/jm9801298

文献信息

• CURABLE LIQUIDS AND INKS FOR TOYS AND FOOD PACKAGING APPLICATIONS
  申请人：Claes Roland

  公开号：US20110124768A1

  公开（公告）日：2011-05-26

  A free radical curable liquid for inkjet printing of food packaging materials includes no initiator or otherwise one or more initiators selected from the group consisting of non-polymeric di- or multifunctional initiators, oligomeric initiators, polymeric initiators, and polymerizable initiators; wherein the polymerizable composition of the liquid consists essentially of: a) 25-100 wt % of one or more polymerizable compounds A having at least one acrylate group G1 and at least one second ethylenically unsaturated polymerizable functional group G2 different from the group G1; b) 0-55 wt % of one or more polymerizable compounds B selected from the group consisting of monofunctional acrylates and difunctional acrylates; and c) 0-55 wt % of one or more polymerizable compounds C selected from the group consisting of trifunctional acrylates, tetrafunctional acrylates, pentafunctional acrylates and hexafunctional acrylates. If the weight percentage of compounds B>24 wt %, then the weight percentage of compounds C>1 wt %; and wherein all weight percentages of A, B and C are based upon the total weight of the polymerizable composition. At least one polymerizable compound B or C is present in the polymerizable composition if the free radical curable liquid contains no initiator. The polymerizable compound A has a copolymerization ratio of 0.002< r 2/ r 1<0.200 with r1 and r2 representing the copolymerization parameters of methyl-G1 respectively methyl-G2 determined according to the method of Kelen-Tudos.

  一种用于食品包装材料的喷墨印刷的自由基可固化液体，不包括引发剂或者选择自非聚合二元或多元引发剂、寡聚引发剂、聚合引发剂和可聚合引发剂中的一种或多种引发剂；其中所述液体的聚合组成物质基本上包括：a）25-100重量％的至少具有一个丙烯酸酯基团G1和至少一个与G1不同的第二个乙烯基不饱和聚合可功能基团G2的一个或多个聚合可化合物A; b）0-55重量％的单官能丙烯酸酯和双官能丙烯酸酯中选择的一个或多个聚合可化合物B；以及c）0-55重量％的三官能丙烯酸酯、四官能丙烯酸酯、五官能丙烯酸酯和六官能丙烯酸酯中选择的一个或多个聚合可化合物C。如果化合物B的重量百分比> 24重量％，则化合物C的重量百分比> 1重量％; 其中A，B和C的所有重量百分比都基于聚合可组分的总重量。如果自由基固化液体不含引发剂，则至少存在一种聚合可化合物B或C在聚合可组分中。聚合可化合物A具有0.002
• RADIATION CURABLE COMPOSITIONS FOR FOOD APPLICATIONS
  申请人：Loccufier Johan

  公开号：US20100304149A1

  公开（公告）日：2010-12-02

  A liquid radiation curable composition for inkjet printing includes a photoinitiating system consisting of one or more diffusion hindered photoinitiators selected from the group consisting of non-polymeric di- or multifunctional initiators, oligomeric or polymeric initiators, and polymerizable initiators, and one or more polymerizable co-initiators, wherein at least one of the polymerizable co-initiators is a polymerizable aromatic tertiary amine. Inkjet inks, an inkjet printing process, and packaging materials may include the liquid radiation curable composition.

  一种用于喷墨打印的液体辐射固化组合物，包括一个光引发系统，该系统由选自非聚合二元或多功能引发剂、寡聚物或聚合物引发剂和可聚合引发剂的一种或多种扩散受阻光引发剂组成，以及一种或多种可聚合共同引发剂，其中至少一种可聚合共同引发剂是可聚合芳香族三级胺。喷墨墨水、喷墨打印过程和包装材料可能包括该液体辐射固化组合物。
• Radiation curable inkjet printing methods
  申请人：Agfa Graphics N.V.

  公开号：EP2053100A1

  公开（公告）日：2009-04-29

  An inkjet printing method comprising the steps of: a) providing a first radiation curable composition curable by free radical polymerization or cationic polymerization; b) applying a layer of the first radiation curable composition on a substrate; c) curing the layer; and d) jetting on the cured layer a second composition curable by a different polymerization than the first composition but selected from the group consisting of free radical polymerization and cationic polymerization characterized in that the first composition comprises a cationically polymerizable compound having at least one (meth)acrylate group in an amount of at least 25 wt% based upon the total weight of the first curable composition.

  一种喷墨打印方法，包括以下步骤 a) 提供可通过自由基聚合或阳离子聚合固化的第一种辐射固化组合物； b) 在基底上涂敷一层第一辐射固化组合物； c) 固化该层；以及 d) 在固化层上喷射可通过与第一种组合物不同的聚合方式固化的第二种组合物，该第二种组合物可从自由基聚合和阳离子聚合组成的组中选择 其特征在于，第一种组合物包括至少具有一个（甲基）丙烯酸酯基团的阳离子可聚合化合物，其含量至少为第一种可固化组合物总重量的 25%。
• Curable liquids and inks for toys and food packaging applications
  申请人：Agfa Graphics N.V.

  公开号：EP2053101A1

  公开（公告）日：2009-04-29

  A free radical curable liquid for inkjet printing of food packaging materials comprising no initiator or otherwise one or more initiators selected from the group consisting of non-polymeric di- or multifunctional initiators, oligomeric initiators, polymeric initiators and polymerizable initiators; wherein the polymerizable composition of said liquid consists essentially of: a) 25 - 100 wt% of one or more polymerizable compounds A having at least one acrylate group G1 and at least one second ethylenically unsaturated polymerizable functional group G2 selected from the group consisting of a vinlyether group, an allylether group and a allylester group; b) 0 - 55 wt% of one or more polymerizable compounds B selected from the group consisting of monofunctional acrylates and difunctional acrylates; and c) 0 - 55 wt% of one or more polymerizable compounds C selected from the group consisting of trifunctional acrylates, tetrafunctional acrylates, pentafunctional acrylates and hexafunctional acrylates, with the proviso that if the weight percentage of compounds B > 24 wt%, then the weight percentage of compounds C > 1 wt%; and wherein all weight percentages of A, B and C are based upon the total weight of the polymerizable composition; and with the proviso that at least one polymerizable compound B or C is present in the polymerizable composition if the free radical curable liquid contains no initiator.

  一种用于喷墨打印食品包装材料的自由基固化液体，不含引发剂，或含有一种或多种引发剂，这些引发剂选自非聚合二或多功能引发剂、低聚引发剂、聚合引发剂和可聚合引发剂组成的组； 其中所述液体的可聚合成分主要包括 a) 25 - 100 wt%的一种或多种可聚合化合物 A，其至少具有一个丙烯酸酯基团 G1 和至少一个第二乙烯基不饱和可聚合官能团 G2，该第二乙烯基不饱和可聚合官能团选自乙烯醚基团、烯丙基醚基团和烯丙基醚基团组成的组； b) 0 - 55 wt%的一种或多种可聚合化合物 B，选自由单官能丙烯酸酯和双 官能丙烯酸酯组成的组；以及 c) 0 - 55 wt%的一种或多种可聚合化合物 C，选自由三官能丙烯酸酯、四官能丙烯酸酯、 五官能丙烯酸酯和六官能丙烯酸酯组成的组，但如果化合物 B 的重量百分比大于 24 wt%，则化合物 C 的重量百分比大于 1 wt%； 其中 A、B 和 C 的所有重量百分比均基于可聚合组合物的总重量；以及 但如果自由基固化液体不含引发剂，则至少有一种可聚合化合物 B 或 C 存在于可聚合组合物中。
• Radiation curable compositions for food applications
  申请人：Agfa Graphics N.V.

  公开号：EP2033949B1

  公开（公告）日：2017-04-19