2-Hexenal-dimethylhydrazon | 102651-78-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Hexenal-dimethylhydrazon
• 英文别名: hex-2-enal-N,N-dimethyl hydrazone；Hex-2-enal-N,N-dimethyl-hydrazon；N-(hex-2-enylideneamino)-N-methylmethanamine
• CAS: 102651-78-5
• 化学式: C₈H₁₆N₂
• 分子量: 140.228
• InChiKey: KSIQSTNLRCGAPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  45 °C(Press: 0.2 Torr)
• 密度：
  0.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-Hexenal-dimethylhydrazon 在 氢氧化钾 、 silver nitrate 、 碘甲烷 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 反式,反式-2,4-庚二烯醛
  参考文献：
  名称：

  Zimmermann, Birgit; Lerche, Holger; Severin, Theodor, Chemische Berichte, 1986, vol. 119, # 9, p. 2848 - 2858

  摘要：

  DOI：
• 作为产物：
  描述：

  glyoxal mono(dimethylhydrazone) 、 正戊酸 生成 2-Hexenal-dimethylhydrazon
  参考文献：
  名称：

  Zimmermann, Birgit; Lerche, Holger; Severin, Theodor, Chemische Berichte, 1986, vol. 119, # 9, p. 2848 - 2858

  摘要：

  DOI：

文献信息

• Cyclopropyl Containing Fatty Acids as Mechanistic Probes for Cytochromes P450
  作者：Max J. Cryle、Paul R. Ortiz de Montellano、James J. De Voss

  DOI：10.1021/jo047985d

  日期：2005.4.1

  isomeric cyclopropyl cations. Ring opening of a radical intermediate in an oxidative transformation is expected to yield a single rearranged alcohol, whereas a cation isomerizes prior to ring opening, leading to two isomeric homoallylic alcohols. Oxidation of these probes by P450BM3 and P450BioI gives results consistent with a radical but not a cationic intermediate in fatty acid hydroxylation by these enzymes

  细胞色素P450引起脂肪族羟基化的机制一直是争论的主题，并提出了几种替代的机制。在这些研究中，各种含环丙基的化合物（自由基钟）可以在氧化时产生未排列和开环的产物，已成为这些研究的关键工具。在这项研究中，我们介绍了几种含环丙基的脂肪酸1a - 4a用它来探索能够进行脂肪酸羟化的P450的机制。由于异构环丙基阳离子的快速平衡，该探针能够区分自由基和阳离子中间体。预期在氧化转化中自由基中间体的开环会产生单个重排的醇，而阳离子在开环之前会异构化，导致生成两种异构的均烯丙基醇。这些探针被P450 BM3和P450 BioI氧化后得到的结果与这些酶在脂肪酸羟基化中的自由基中间体而不是阳离子中间体一致。未重排的和开环的产物的定量给出显着均匀的速率的（2-3）氧反弹×10个10小号-1。讨论了将环丙烷环引入脂肪酸中对羟基化的区域化学的影响。
• Structure-Antitumor Activity Relationships of Aza- and Diaza-Anthracene-2,9,10-Triones and Their Partially Saturated Derivatives
  作者：Carmen Avendaño、Pilar López-Alvarado、José María Pérez、Miguel Ángel Alonso、Eva Pascual-Alfonso、Miriam Ruiz-Serrano、J. Carlos Menéndez

  DOI：10.3390/molecules29020489

  日期：——

  relationships. From the results obtained, we conclude that some representatives of the 1,8-diazaanthracene-2,9,10-trione framework show potent and selective cytotoxicity against solid tumors. Similar findings were made for the related 1-azaanthracene-2,9,10-trione derivatives, structurally similar to the marcanine natural products, which showed improved activity over their natural counterparts. An enantioselective

  1,8-二氮杂蒽-2,9,10-三酮，它们的 5,8-二氢衍生物和 1,8-二氮杂蒽-2,7,9,10-四酮，在结构上与二氮杂喹啉菌素家族天然产物相关，采用 Diels-Alder 策略以区域选择性方式合成。研究了这些文库在各种人类癌细胞系中的细胞毒性，以建立结构-活性关系。从获得的结果中，我们得出结论，1,8-二氮杂蒽-2,9,10-三酮框架的一些代表对实体瘤显示出有效的选择性细胞毒性。相关的 1-氮杂蒽-2,9,10-三酮衍生物也发现了类似的结果，它们在结构上与 marcanine 天然产物相似，其活性优于天然产物。针对手性 5 取代的 1,8-二杂蒽-2,9,10-三酮的情况开发了一种基于使用 SAMP 相关手性衍生的对映选择性方案，并表明它们的细胞毒性不是对映特异性的。
• Duhamel,L.; Valnot,J.-Y., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1978, vol. 286, p. 47 - 50
  作者：Duhamel,L.、Valnot,J.-Y.

  DOI：——

  日期：——
• Nasakin, O. E.; Sheverdov, V. P.; Lukin, P. M., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 9.1, p. 1475 - 1481
  作者：Nasakin, O. E.、Sheverdov, V. P.、Lukin, P. M.、Tafeenko, V. A.、Bulai, A. Kh.

  DOI：——

  日期：——
• Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors
  作者：Na Liu、Hua Zhong、Jie Tu、Zhigan Jiang、Yanjuan Jiang、Yan Jiang、Yuanying Jiang、Jian Li、Wannian Zhang、Yan Wang、Chunquan Sheng

  DOI：10.1016/j.ejmech.2017.10.043

  日期：2018.1

  Lack of novel antifungal agents and severe drug resistance have led to high incidence and associated mortality of invasive fungal infections. To tackle the challenges, novel antifungal agents with new chemotype, fungicidal activity and anti-resistant potency are highly desirable. On the basis of our previously identified simplified analogue of antifungal natural product sampangine, systemic structure-activity relationships were clarified and two novel derivatives showed promising features as novel antifungal lead compounds. Compounds 22b and 22c showed good fungicidal activity against both fluconazole-sensitive and fluconazole-resistant Candida albicans strains. Moreover, they were proven to be potent inhibitors of Candida albicans biofilm formation and yeast-to-hypha morphological transition by down-regulating biofilm-associated genes. In a rat vaginal Candida albicans infection model, compounds 22b and 22c showed excellent therapeutic effects with low toxicity. The results highlighted the potential of sampangine derivatives to overcome fluconazole-related and biofilm-related drug resistance. (C) 2017 Elsevier Masson SAS. All rights reserved.