N-Benzyl-N'-furan-2-ylmethyl-oxalamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Benzyl-N'-furan-2-ylmethyl-oxalamide
• 英文别名: N-Furfuryl-N'-(benzyl)oxamide；N-benzyl-N'-(furan-2-ylmethyl)oxamide
• 化学式: C₁₄H₁₄N₂O₃
• mdl: MFCD00433693
• 分子量: 258.277
• InChiKey: XCPWKFNWWZVSJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-((furan-2-ylmethyl)amino)-2-oxoacetate 在 sodium hydroxide 、 甲烷磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.33h， 生成 N-Benzyl-N'-furan-2-ylmethyl-oxalamide
  参考文献：
  名称：

  Preparation and Plant Growth-Regulatory Activity of N'-Substituted N-Furfuryloxamides.

  摘要：

  N'-取代的N-糠酰胺（4）是通过草酸钾（8）与糠胺（5f）在1,1'-草酰二咪唑（6）的作用下缩合，然后对生成的酰胺-酯（10）进行水解，最后与脂肪族或芳香族胺（5）进一步缩合制备而成的。制备的化合物（4）被检测作为植物生长调节剂的活性，使用两种植物种子进行测试，分别是油菜，芸薹属植物（双子叶植物）和韭菜，葱属植物（单子叶植物）。N'-苄基和N'-苯基-N-糠酰胺（4b和4c）以及N,N'-二糠酰胺（4f）抑制了这两种植物幼苗的根生长。

  DOI：

  10.1248/cpb.46.514

文献信息

• Preparation and Plant Growth-Regulatory Activity of N-Chloro-Substituted Phenyl- and Benzyl-N-furfuryloxamides.
  作者：Tokujiro KITAGAWA、Chinatsu TSUTSUI

  DOI：10.1248/cpb.46.1308

  日期：——

  N'-Chlorophenyl- and N'-chlorobenzyl-N-furfuryloxamides (6b-e and 7b-d) were synthesized through the reaction of chloro-substituted anilines (12b-e) or chloro-substituted benzylamines (13b-d) with N-furfuryloxamic acid sodium salt (10), which was prepared via condensation of methyl oxalate (8) with furfurylamine, followed by hydrolysis of the resulting amide-ester with sodium hydroxide. The activity of the prepared compounds (6 and 7) as plant growth regulators was examined by a germination assay using rape and leek seeds.N'-(3-Chlorophenyl)-N-furfuryloxamide (6c) showed a little effectiveness as an inhibitor, whereas the parent compound, N'-phenyl-N-furfuryloxamide (6a) inhibited the root growth of rape seedlings. The 2-chlorophenyl derivative (6b) inhibited the root growth of rape seedlings as potently as 6a, but sufficiently promoted the root growth of leek seedlings. Further, the 4-chlorophenyl derivative (6d) promoted the root growth of both species. On the other hand, in the series of chlorinated benzyl derivatives (7b-d), N'-(3-chlorobenzyl)-N-furfuryloxamide (7c) showed a markedly superior inhibitory effect in both species, but 2- and 4-chlorobenzyl derivatives (7b and 7d) inhibited the root growth of only rape seedlings.

  通过氯代苯胺（12b-e）或氯代苄胺（13b-d）与 N-糠酰氧肟酸钠盐（10）反应合成了 N'-氯苯基和 N'-氯苄基-N-糠酰氧肟（6b-e 和 7b-d），后者是通过草酸甲酯（8）与糠胺缩合，然后用氢氧化钠水解生成的酰胺酯制备的。N'-(3- 氯苯基)-N-糠酰草胺（6c）作为一种抑制剂显示出很小的效力，而母体化合物 N'- 苯基-N-糠酰草胺（6a）则抑制油菜幼苗根部的生长。2-chlorophenyl 衍生物（6b）对油菜幼苗根系生长的抑制作用不亚于 6a，但却能充分促进韭菜幼苗的根系生长。此外，4-氯苯基衍生物（6d）对这两种植物的根系生长都有促进作用。另一方面，在氯化苄基衍生物系列（7b-d）中，N'-（3-氯苄基）-N-糠基环氧酰胺（7c）对两种植物的抑制作用都很明显，但 2-和 4-氯苄基衍生物（7b 和 7d）只抑制油菜幼苗的根系生长。
• Preparation and Plant Growth-Regulatory Activity of N'-Substituted N-Furfuryloxamides.
  作者：Tokujiro KITAGAWA、Chinatsu TSUTSUI、Kumi HAYASHI、Aiko YAMANO

  DOI：10.1248/cpb.46.514

  日期：——

  N'-Substituted N-furfuryloxamides (4) were prepared via condensation of potassium methyl oxalate (8) with furfurylamine (5f) using 1, 1'-oxalyldiimidazole (6), followed by hydrolysis of the resulting amide-ester (10), and finally condensation with aliphatic or aromatic amines (5). The prepared compounds (4) were examined for activity as plant growth regulators using two kinds of plant seeds, namely, those of rape, Brassica campestris L. (Dicotyledoneae) and leek, Allium tuberosum ROTTLER (Monocotyledoneae). N'-Benzyl- and N'-phenyl-N-furfuryloxamides (4b and 4c) and N, N'-difurfuryloxamide (4f) inhibited root growth in seedlings of both species.

  N'-取代的N-糠酰胺（4）是通过草酸钾（8）与糠胺（5f）在1,1'-草酰二咪唑（6）的作用下缩合，然后对生成的酰胺-酯（10）进行水解，最后与脂肪族或芳香族胺（5）进一步缩合制备而成的。制备的化合物（4）被检测作为植物生长调节剂的活性，使用两种植物种子进行测试，分别是油菜，芸薹属植物（双子叶植物）和韭菜，葱属植物（单子叶植物）。N'-苄基和N'-苯基-N-糠酰胺（4b和4c）以及N,N'-二糠酰胺（4f）抑制了这两种植物幼苗的根生长。