4-[N,N'-diphenyl(bis(hydrazonoyldichlorides))]benzene | 6645-67-6

• 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: 4-[N,N'-diphenyl(bis(hydrazonoyldichlorides))]benzene
• 英文别名: 1,4-diphenylterephthalohydrazonoyl dichloride；1,4-diphenylterephthaloyhydrazoonoyl dichloride；1,4-Bis-(phenylhydrazono-chlormethyl)-benzol；1-N,4-N-diphenylbenzene-1,4-dicarbohydrazonoyl chloride
• CAS: 6645-67-6
• 化学式: C₂₀H₁₆Cl₂N₄
• 分子量: 383.28
• InChiKey: UPHJKWZBPMIXBY-UHFFFAOYSA-N

物化性质

• 熔点：
  190-200 °C
• 沸点：
  514.8±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.78
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[N,N'-diphenyl(bis(hydrazonoyldichlorides))]benzene 在 溶剂黄146 、 sodium nitrite 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 水 为溶剂， 反应 0.25h， 生成 1,4-bis-(2-oxo-3-phenyl-3H-[1,3,4]selenadiazol-5-yl) benzene
  参考文献：
  名称：

  A New Strategy for Synthesis of Novel 1, 4-Phenylene Bridged Bis-Hetero - Cyclic Compounds

  摘要：

  二氢腙基氯1与KSCN和KSeCN分别反应，生成了相应的双硫二氮杂环2A和双硒二氮杂环2B。通过1与适当的活性亚甲基化合物的反应，还得到了双吡唑衍生物7a-e和8a-b。1与二氰基乙烯、苊烯和苯基-5-芳亚甲基-2-硫酮-噻唑-4-酮作为双极亲偶体的反应分别导致了相应的环加成产物9、12和14的形成。此外，二氢腙基氯1与三嗪硫酮16a-e反应生成了1,4-双-(1,2,4-三唑三嗪)苯17a-e。所制备化合物的结构是根据元素和光谱分析以及它们的化学反应来确定的。

  DOI：

  10.2174/1570178613666160824104435

文献信息

• New Route Synthesis of Thiadiazoles, Bisthiadiazoles, Thiadiazolotriazines, and Pyrazolothiadiazoles Based on Hydrazonoyl Halides and Dihydrazinylthiadiazole
  作者：Abdelwahed Sayed、Shar Al-Shihry

  DOI：10.3390/molecules22020336

  日期：——

  Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds

  研究了新的噻二唑、双噻二唑的合成和表征，这些化合物来自单-和二-腙酰卤与各种肼碳二硫代衍生物的反应。用2,5-二肼基-1,3,4-噻二唑处理腙酰卤，得到含有噻二唑的新型双三嗪；我们还研究了 2,5-二肼基-1,3,4-噻二唑与活性亚甲基化合物的反应，以提供含有噻二唑化合物的新型吡唑。通过元素分析和各种光谱数据（傅里叶变换红外光谱、质谱、1H 和 13C 核磁共振）鉴定了新合成的化合物。
• Regioselective Synthesis of 5-Trifluoromethylpyrazoles by [3 + 2] Cycloaddition of Nitrile Imines and 2-Bromo-3,3,3-trifluoropropene
  作者：Hao Zeng、Xiaojie Fang、Zhiyi Yang、Chuanle Zhu、Huanfeng Jiang

  DOI：10.1021/acs.joc.0c02765

  日期：2021.2.5

  A general and practical method for the synthesis of 5-trifluoromethylpyrazoles is reported that occurs by the coupling of hydrazonyl chlorides with environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP). This exclusively regioselective [3 + 2] cycloaddition of nitrile imines and with BTP is catalyst-free and operationally simple and features mild conditions

  据报道，通过将酰氯与环境友好的大吨位工业原料2-溴-3,3,3-三氟丙烯（BTP）偶合，可以合成5-三氟甲基吡唑的通用方法。腈亚胺和BTP的这种唯一的区域选择性[3 + 2]环加成反应无催化剂，操作简单，具有温和的条件，高收率，可克级缩放，广泛的底物范围和有价值的官能团耐受性。重要的是，我们的方法已用于合成鞘氨醇1-磷酸受体活性激动剂的关键中间体。
• Synthesis of novel bis-thiadiazoles, bis-triazoles and polypyrazole derivatives based on hydrazonoyl halides
  作者：Abdelwahed R. Sayed

  DOI：10.1016/j.tet.2013.04.137

  日期：2013.7

  A series of novel bis-thiadiazoles and bis-triazoles derivatives were synthesized via the reaction of hydrazonoyl halides with different moieties. Also, the synthesis and mechanism for polypyrazole formation are described via reaction of bis-hydrazonoyl with p-benzoquinone. Synthesized compounds were elucidated by elemental analysis and spectral data.

  通过酰卤与不同部分的反应合成了一系列新型的双噻二唑和双三唑衍生物。而且，通过双hydr酰基与对苯醌的反应描述了聚吡唑的合成和机理。通过元素分析和光谱数据阐明了合成的化合物。
• A convenient route for the synthesis of new thiadiazoles
  作者：Abdelwahed SAYED、Yasser ZAKI、Emad AISH

  DOI：10.3906/kim-1505-13

  日期：——

  The present work describes the preparation of new thiadiazoles through a simple intramolecular reaction of mono- and bis-hydrazonoyl halides with methyl hydrogen phenyl carbonimidodithioate or methyl-2-arylidene hydrazinecarbodithioate. The synthetic method involves nucleophilic substitution followed by intramolecular cyclization reactions mediated by evolution of methanethiol. The structures of the title compounds were elucidated by elemental analyses, and FTIR, MS and NMR spectra.

  目前的工作描述了通过单亚肼基卤化物和双亚肼酰卤与甲基氢苯基碳酰亚胺二硫代酸酯或甲基-2-亚芳基肼碳二硫代酸酯的简单分子内反应制备新型噻二唑。该合成方法涉及亲核取代，然后是由甲硫醇的演化介导的分子内环化反应。通过元素分析、FTIR、MS 和 NMR 光谱阐明了标题化合物的结构。
• Convenient Methods for the Synthesis of Novel Thiadiazoles and Polythiadiazoles
  作者：Abedlwahed R. Sayed、Yasair S. Al-Faiyz

  DOI：10.3987/com-20-14254

  日期：——

  In this study, the novel thiadiazoles were formed via the reaction of hydrazonoyl halides with methyl 2-(adamantan-2-ylidene)hydrazinecarbodithioate. Also, the reaction of 2,5-dihydraziny1-1,3,4-thiadiazoles with 2-adamantanone or acetylferrocene produced the 2,5-bis(2-(adamantan-2-ylidene)hydraziny1)1,3,4-thiadiazole or 2,5-bis(2-(1-(ferrocenylidene)hydraziny1)-1,3,4-thiadiazole, respectively. Analogously, treatment of terephthalaldehyde with 2,5-dihydrazinyl-1,3,4-thiadi azole afforded new poly(benzylidenehydraziny1-1,3,4-thiadiazole). Finally, the reaction of bishydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new poly(1,3,4-thiadiazolo[2,3-c][1,2,4]triazine). The synthetic structures for the final products are suggested and discussed. The compound structures of the products were recognized by different spectroscopic analyses.