1,1-dimethyl-2-(2-methylallylidene)hydrazine | 25368-52-9

• 物质功能分类: 化学试剂 - 有机试剂 - 腙
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,1-dimethyl-2-(2-methylallylidene)hydrazine
• 英文别名: acrolein N,N-dimethylhydrazone；acrolein-N,N-dimethylhydrazone；acrolein dimethylhydrazone；Propenal-dimethylhydrazon；propenal N,N-dimethylhydrazone；Dimethylhydrazon v. Acrolein；N-methyl-N-(prop-2-enylideneamino)methanamine
• CAS: 25368-52-9
• 化学式: C₅H₁₀N₂
• 分子量: 98.1478
• InChiKey: QPQDIJVEDXZVBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-dimethyl-2-(2-methylallylidene)hydrazine 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 生成 二甲氨基丙腈
  参考文献：
  名称：

  Koldobskii, A. B.; Kharchevnikov, A. P.; Lunin, V. V., Doklady Chemistry, 1987, vol. 293, p. 169 - 171

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Dimethylamino)propanal-dimethylhydrazon 在 4-硝基苯甲酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以67%的产率得到1,1-dimethyl-2-(2-methylallylidene)hydrazine
  参考文献：
  名称：

  Habernegg, Renate; Severin, Theodor, Chemische Berichte, 1986, vol. 119, # 8, p. 2397 - 2413

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents
  作者：Don Antoine Lanfranchi、Elena Cesar-Rodo、Benoît Bertrand、Hsin-Hung Huang、Latasha Day、Laure Johann、Mourad Elhabiri、Katja Becker、David L. Williams、Elisabeth Davioud-Charvet

  DOI：10.1039/c2ob25812a

  日期：——

  polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels–Alder reaction. The antimalarial and the antischistosomal activities of these polysubstituted aza-1,4-naphthoquinone derivatives were evaluated and led to

  通过基于区域选择性杂化的两步直接合成，在萘醌核心的两个不同位置（甲萘醌的 C-5 和 C-8）引入氮，从而提高多取代 1,4-萘醌衍生物的溶解度。狄尔斯-阿尔德反应。对这些多取代氮杂-1,4-萘醌衍生物的抗疟和抗血吸虫活性进行了评估，并选择了具有抗疟和抗血吸虫作用的不同化合物。使用 AgNO 3和过二硫酸铵对Ag II辅助的苯乙酸氧化自由基脱羧进行修饰，生成具有改善的药代动力学参数、高抗疟作用和抑制 β-血红素形成能力的 3-吡啶甲基甲萘醌。
• Inverse-electron-demand Diels–Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones
  作者：Yoshimitsu Hashimoto、Ryo Abe、Nobuyoshi Morita、Osamu Tamura

  DOI：10.1039/c8ob02132e

  日期：——

  of 3-electron-withdrawing group substituted α-pyrones with α,β-unsaturated hydrazones as electron-rich counterparts are catalyzed by Eu(hfc)3 to afford bicyclic lactone cycloadducts. This is an example of umpolung cycloaddition based on functional transformation of carbonyls to hydrazones. A subsequent dehydrazonation reaction enables indirect synthesis of carbonyl group-containing bicyclic lactones

  Eu（hfc）3催化3吸电子基团取代的α-吡喃酮与富电子的α，β-不饱和酮的反电子需求Diels-Alder反应，由Eu（hfc）3催化，得到双环内酯环加合物。这是基于羰基向to的功能转化的环酚加成的例子。随后的脱水反应使得能够间接合成含羰基的双环内酯，而这是不容易通过α-吡喃酮和烯醛的环加成而获得的。
• Synthesis and in vitro antitumor activity of an isomer of the marine pyridoacridine alkaloid ascididemin and related compounds
  作者：Evelyne Delfourne、Robert Kiss、Laurent Le Corre、Joumaa Merza、Jean Bastide、Armand Frydman、Francis Darro

  DOI：10.1016/s0968-0896(03)00483-8

  日期：2003.10

  The isomer (9H-quino[4,3,2-de][1,7]phenanthroline-9-one) (2) of the marine alkaloid ascididemin (9H-quino[4,3,2-de][1,10]phenanthroline-9-one) (1) has been synthesized in six steps from 1,4-dimethoxyacridine (10) with an overall yield of 12%. Different related compounds were prepared and tested in vitro at six different concentrations on 12 different human cancer cell lines of various histopathological

  海洋生物碱阿西地敏（9H-quino [4,3,2-de] [1，的异构体（9H-quino [4,3,2-de] [1,7]菲咯啉-9-one）（2）由1，4-二甲氧基one啶（10）以六步合成10]菲咯啉-9-一）（1），总产率为12％。制备了不同的相关化合物，并以六种不同的浓度在体外在12种不同的组织病理学类型（胶质母细胞瘤和乳腺癌，结肠癌，肺癌，前列腺癌和膀胱癌）的人类癌细胞系中进行了测试。几乎所有化合物都表现出微摩尔级的细胞毒活性。
• The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
  作者：Christophe Morin、Tatiana Besset、Jean-Claude Moutet、Martine Fayolle、Margit Brückner、Danièle Limosin、Katja Becker、Elisabeth Davioud-Charvet

  DOI：10.1039/b802649c

  日期：——

  Various aza-analogues of 1,4-naphthoquinone and menadione were prepared and tested as inhibitors and substrates of the plasmodial thioredoxin and glutathione reductases as well as the human glutathione reductase. The replacement of one to two carbons at the phenyl ring of the 1,4-naphthoquinone core by one to two nitrogen atoms led to an increased oxidant character of the molecules in accordance with both the redox potential values and the substrate efficiencies. Compared to the 1,4-naphthoquinone and menadione, the quinoline-5,8-dione 1 and both quinoxaline-5,8-diones 5 and 6 behaved as the most efficient subversive substrates of the three NADPH-dependent disulfide reductases tested. Modulation of these parameters was observed by alkylation of the aza-naphthoquinone core.

  制备并测试了 1,4萘醌和甲萘醌的各种杂环类似物，并将其作为质体硫氧还蛋白酶和谷胱甘肽还原酶以及人类谷胱甘肽还原酶的抑制剂和底物。根据氧化还原电位值和底物效率，将 1,4-萘醌核心苯基环上的一到两个碳原子替换为一到两个氮原子可增加分子的氧化特性。与 1,4-萘醌和甲萘醌相比，喹啉-5,8-二酮 1 以及喹喔啉-5,8-二酮 5 和 6 是所测试的三种 NADPH 依赖性二硫还原酶最有效的颠覆性底物。通过对氮杂萘醌核心进行烷基化，可以观察到这些参数的变化。
• Addition reactions of 1,1,1-trifluoro-4-trimethylstannylbut-3-yn-2-one and 1,1,1-trifluorobut-3-yn-2-one to some tetrahydropyridines. Synthesis of trifluoroacylated polysubstituted tetrahydroazocines
  作者：A. B. Koldobskii、E. V. Solodova、V. N. Kalinin

  DOI：10.1007/s11172-010-0197-x

  日期：2010.5

  A reaction of tetrahydropyridines, obtained by the Diels-Alder reaction from α,β-unsat-urated N,N-dimethylhydrazones and methyl acrylate, with acetylenes activated with the trifluoroacetyl group has been studied and found to lead to polysubstituted trifluoroacylated tetrahydroazocines. No cyclobutene intermediates have been detected.

  已经研究了通过由 α,β-不饱和 N,N-二甲基腙和丙烯酸甲酯的 Diels-Alder 反应获得的四氢吡啶与用三氟乙酰基活化的乙炔的反应，并发现会产生多取代的三氟酰化四氢偶氮辛。没有检测到环丁烯中间体。