methacrolein dimethylhydrazone | 16713-45-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methacrolein dimethylhydrazone
• 英文别名: 3-methyl-1-dimethylamino-1-azabuta-1,3-diene；methacrolein N,N-dimethylhydrazone；1,1-Dimethyl-2-(2-methylprop-2-en-1-ylidene)hydrazine；N-methyl-N-(2-methylprop-2-enylideneamino)methanamine
• CAS: 16713-45-4
• 化学式: C₆H₁₂N₂
• 分子量: 112.175
• InChiKey: QNIXILGOUVOCEP-UHFFFAOYSA-N

物化性质

• 沸点：
  56 °C(Press: 29 Torr)
• 密度：
  0.8492 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methacrolein dimethylhydrazone 、 4-(phenylimino)cyclohexa-2,5-dienone 以 甲苯 为溶剂， 反应 0.5h， 以90 mg的产率得到2-((2,2-dimethylhydrazineylidene)methyl)-2-methyl-N-phenyl-2,3-dihydrobenzofuran-5-amine
  参考文献：
  名称：

  Synthesis of 5-substituted 2,3-dihydrobenzofurans in a one-pot oxidation/cyclization reaction

  摘要：

  Variously substituted 2,3-dihydrobenzofurans have been synthesized according :o a sequential one-pot oxidation/cyclization procedure between para-aminophenol derivatives and an azadiene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.020
• 作为产物：
  描述：

  2-溴-2-甲基丙醛 、 偏二甲肼 生成 methacrolein dimethylhydrazone
  参考文献：
  名称：

  Duhamel,L.; Valnot,J.-Y., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1978, vol. 286, p. 47 - 50

  摘要：

  DOI：

文献信息

• Antitumour 1,5-diazaanthraquinones
  申请人：——

  公开号：US20020099066A1

  公开（公告）日：2002-07-25

  1 Compounds having formula (I) wherein R 3 , R 4 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, lower alkyl, halogen, amine, mono(lower)alkylamine, di(lower)alkylamine, phenyl, or substituted phenyl possess antitumor activity and are new with the exception of the compound in which R 3 , R 4 , R 7 , R 8 are all hydrogen and the compound in which R 3 and R 7 are hydrogen, R 4 chlorine, and R 8 is a 2-nitrophenyl group.

  具有公式(I)的化合物，其中R3、R4、R7和R8独立地选自包括氢、低级烷基、卤素、胺、单（低级）烷基胺、二（低级）烷基胺、苯基或取代苯基的组，具有抗肿瘤活性，除了R3、R4、R7、R8均为氢的化合物和R3和R7为氢，R4为氯，R8为2-硝基苯基的化合物外，都是新的。
• 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 structure-activity relationship of furoquinolinediones as inhibitors of Tyrosyl-DNA phosphodiesterase 2 (TDP2)
  作者：Le-Mao Yu、Zhu Hu、Yu Chen、Azhar Ravji、Sophia Lopez、Caroline B. Plescia、Qian Yu、Hui Yang、Monica Abdelmalak、Sourav Saha、Keli Agama、Evgeny Kiselev、Christophe Marchand、Yves Pommier、Lin-Kun An

  DOI：10.1016/j.ejmech.2018.04.024

  日期：2018.5

  Tyrosyl-DNA phosphodiesterase 2 (TDP2) is a recently discovered enzyme specifically repairing topoisomerase II (TOP2)-mediated DNA damage. It has been shown that inhibition of TDP2 synergize with TOP2 inhibitors. Herein, we report the discovery of the furoquinolinedione chemotype as a suitable skeleton for the development of selective TDP2 inhibitors. Compound 1 was identified as a TDP2 inhibitor as a result

  酪氨酰-DNA磷酸二酯酶2（TDP2）是最近发现的一种酶，可特异性修复拓扑异构酶II（TOP2）介导的DNA损伤。已经显示出对TDP2的抑制与TOP2抑制剂协同作用。在此，我们报告了呋喃喹啉二酮化学型作为开发选择性TDP2抑制剂的合适骨架的发现。通过筛选内部化合物库中对TDP2和TDP1有选择性的化合物，化合物1被确定为TDP2抑制剂。进一步的SAR研究提供了几种在低微摩尔范围内的选择性TDP2抑制剂。最有效的化合物74对全细胞提取物（WCE）中的重组TDP2和TDP2表现出抑制活性，IC50分别为1.9和2.1μM。
• Antineoplastic heteronapthoquinones
  申请人：Biochem Pharma Inc.

  公开号：US05736523A1

  公开（公告）日：1998-04-07

  This invention relates to a naphthoquinone derivatives, to processes and to intermediates for preparing these derivatives, to pharmaceutical composition and to the use of these derivatives as antitumor agents in mammals.

  这项发明涉及萘醌衍生物，涉及制备这些衍生物的过程和中间体，涉及制药组合物以及将这些衍生物作为抗肿瘤药物在哺乳动物中使用的方法。