4,6-dioctyloxy-1,3-dibenzoic acid dihydrazide | 787629-25-8

• 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: 4,6-dioctyloxy-1,3-dibenzoic acid dihydrazide
• 英文别名: 4,6-Bis(octyloxy)isophthalohydrazide；4,6-dioctoxybenzene-1,3-dicarbohydrazide
• CAS: 787629-25-8
• 化学式: C₂₄H₄₂N₄O₄
• 分子量: 450.622
• InChiKey: FYMGMUNOUNUSEU-UHFFFAOYSA-N

物化性质

• 熔点：
  >258 °C(Solv: ethanol (64-17-5))
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-dioctyloxy-1,3-dibenzoic acid dihydrazide 在 吡啶 、 4-二甲氨基吡啶 、 肼 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 N,N'-di-((2-methoxy-3-hydrazinocarbonylbenzoyl)amino) 4,5-dioctyloxy-iso-phthalamide
  参考文献：
  名称：

  氢键寡酰肼折叠体及其对糖类的识别

  摘要：

  本文描述了第一系列氢键驱动的酰肼折叠体的合成和表征及其对氯仿中烷基糖的识别。低聚物 1、2-4、5、6 和 7 分别含有 1、2、4、6 或 12 个重复的二苯甲酰肼残基，已被制备。1 和 2 或 4 的刚性和平面构象已通过 X 射线分析和 (1) H NMR 光谱确定，而 5-7 的折叠和螺旋构象已通过 1D 和 2D (1) H NMR 证实和红外光谱和分子力学计算。分子力学计算还表明，5、6 和 7 具有一个大小为约 2 的刚性空腔。10.6 到 11.1 A，折叠构象中的羰基的一半在腔内向内定向。(1) H NMR 和 CD 实验表明，5-7 在氯仿中有效地复合烷基化单糖和二糖 32-35。用 (1) H 核磁共振和荧光滴定方法确定了配合物的关联常数 (K(assoc))。6.34 的能量最小化构象已通过分子力学计算获得。这里描述的基于酰肼的折叠结构代表了氢键驱动的折叠体的新例子，它们作为人工受体进行选择性分子识别。

  DOI：

  10.1021/ja047436p
• 作为产物：
  描述：

  dimethyl 4,6-dioctyloxy-1,3-benzenedicarboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以59%的产率得到4,6-dioctyloxy-1,3-dibenzoic acid dihydrazide
  参考文献：
  名称：

  联苯肼的氧化偶合聚合反应合成聚（二酰肼）：可氧化降解聚合物的氧化制备

  摘要：

  成功地进行了双酰肼的氧化偶联聚合反应，以形成聚（二酰肼）（PDAH），它是一种可氧化降解的聚合物。Oxone是一种有效的氧化剂，非质子极性溶剂，水和乙腈或N，N-二甲基乙酰胺的混合物是必需的溶剂。用次氯酸钠溶液或过氧化氢处理PDAH时，PDAH迅速氧化并降解为相应的二羧酸。当使用过氧化氢作为氧化剂时，为了有效降解，必须添加乙腈和碳酸钾。PDAH在空气中表现出高的热稳定性，并具有高的T g价值。在空气中未观察到氧化。因此，PDAH是一种可氧化降解的高性能聚合物，对氧气稳定。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2012年

  DOI：

  10.1002/pola.26225

文献信息

• Polyhydrazide‐Based Organic Nanotubes as Efficient and Selective Artificial Iodide Channels
  作者：Arundhati Roy、Himanshu Joshi、Ruijuan Ye、Jie Shen、Feng Chen、Aleksei Aksimentiev、Huaqiang Zeng

  DOI：10.1002/anie.201916287

  日期：2020.3.16

  molecular weight of 18.2 kDa and 3.6 nm in helical height, exhibits the highest anion-transport activities for iodide (EC50 =0.042 μm or 0.028 mol % relative to lipid), whcih is transported 10 times more efficiently than chlorides (EC50 =0.47 μm). Notably, even in cholesterol-rich environment, iodide transport activity remains high with an EC50 of 0.37 μm. Molecular dynamics simulation studies confirm that

  本文报道了一系列基于氢键酰肼主链的含孔聚合物纳米管。合适长度的纳米管具有直径约 6.5 Å 的中空腔，可介导多种类型的阴离子（而不是阳离子）穿过脂质膜的高效运输。所报道的聚合物通道平均分子量为 18.2 kDa，螺旋高度为 3.6 nm，对碘化物表现出最高的阴离子传输活性（EC50 = 0.042 μm 或相对于脂质的 0.028 mol%），其传输效率提高了 10 倍高于氯化物 (EC50 =0.47 μm)。值得注意的是，即使在富含胆固醇的环境中，碘化物转运活性仍然很高，EC50 为 0.37 μm。分子动力学模拟研究证实，该通道对阴离子具有高度选择性，并且这种阴离子选择性源于由指向内部的甲基所呈现的中央腔的正静电势。
• Helical Molecular Duplex Strands:  Multiple Hydrogen-Bond-Mediated Assembly of Self-Complementary Oligomeric Hydrazide Derivatives
  作者：Yong Yang、Zhi-Yong Yang、Yuan-Ping Yi、Jun-Feng Xiang、Chuan-Feng Chen、Li-Jun Wan、Zhi-Gang Shuai

  DOI：10.1021/jo070525a

  日期：2007.6.1

  X-ray structure of a ditopic hydrazide derivative 7 led to the concept that with malonyl groups as interhydrazide linkers hydrogen-bonding-mediated molecular duplex strands might be obtained. Complexation studies between 7, 8, and 9 confirmed this hypothesis. Two quadruple hydrogen-bonded heterodimers formed, in which spectator repulsive secondary electrostatic interaction was found to play an important

  仔细检查对位酰肼衍生物7的X射线结构，得出了这样一个概念，即丙二酰基作为酰肼间连接基，可以得到氢键介导的分子双链。的络合作用研究7，8和9证实了这一假设。形成了两个四氢键合的异二聚体，其中观众排斥性的次级静电相互作用被发现在确定配合物的稳定性中起重要作用。在大量的研究1 - 4指出氢键模式可以在更长的低聚酰肼衍生物中持续存在，其链从单体延伸到四聚体。通过两个到十四个链间氢键获得分子双链体。除了影响双链的稳定性外，旁观者的排斥性二次静电相互作用在确定双链的动态行为方面也起着重要作用，如可变温度1 H NMR实验所示。红外研究证实，较长的低聚物中的氢键较强。1 − 4的装配STM技术也研究了HOPG的性能。分子力学计算进一步揭示了较长寡聚物的双螺旋结构。结果为开发具有明确结构的聚合物螺旋双链体提供了新的机会。
• Amidourea-Based Hydrogen-Bonded Heteroduplexes: Structure and Assembling Selectivity
  作者：Wei-Jun Chu、Jianming Chen、Chuan-Feng Chen、Yong Yang、Zhigang Shuai

  DOI：10.1021/jo301434a

  日期：2012.9.21

  A new class of multiply hydrogen-bonded heteroduplexes from readily available amidourea derivatives was designed, and their structures and selective assembling behaviors were investigated. Amidourea derivative 3 could selectively assemble with 1 to form a stable heteroduplex via eight intermolecular bifurcated hydrogen bonds, but could not assemble with 2 at all, because of their unique structures and the spacing effect, although 1 and 2 possessed the same hydrogen-bonding sequence. The high stability and selectivity will make the amidourea-based hydrogen-bonded heteroduplexes be potentially applicable in the design of well-defined supramolecular architectures and novel functional materials.
• Dynamic Decomposition/Recombination of Hydrogen Bonds in Molecular Duplex Strands
  作者：Yong Yang、Jun-Feng Xiang、Chuan-Feng Chen

  DOI：10.1021/ol701868w

  日期：2007.10.1

  Dynamic decomposition/recombination of hydrogen bonds in the hydrazide based molecular duplex strands was explored by variable-temperature H-1 NMR experiments. A shuttle-like dynamic process of the two constituent molecules of the duplex strands between two degenerate states was observed.
• Supramolecular Substitution Reactions between Hydrazide-Based Molecular Duplex Strands: Complexation Induced Nonsymmetry and Dynamic Behavior
  作者：Yong Yang、Jun-Feng Xiang、Min Xue、Hai-Yu Hu、Chuan-Feng Chen

  DOI：10.1021/jo801139p

  日期：2008.8.1

  [GRAPHICS]Supramolecular substitution reactions between hydrazide-based oligomers 1a-c and 2a-c were systematically investigated. Each oligomer existed as hydrogen-bonding mediated molecular duplex strands or a polymeric zipper structure in apolar solvents. But when another oligomer with complementary hydrogen bonding sites was added, a heterodimer structure formed due to supramolecular substitution reaction driven by the formation of more hydrogen bonds, which was evidenced by NMR experiments, sometimes gel-sol transition. When a nonsymmetric oligomer and a symmetric oligomer were involved, complexation-induced nonsymmetry was observed. When two nonsymmetric oligomers were involved, two hydrogen-bonded isomers were observed in solution. Variable-temperature H-1 NMR experiments further revealed unique dynamic behavior for the individual oligomer and the complexes. When diacetyl-terminated oligomer 1c was involved, slides perpendicular to hydrogen bonds between two constituent molecules were observed, which led to complicated 1H NMR spectra at lower temperature; otherwise, high selectivity was obtained. Combined with the results we reported previously, a detailed picture of the structure-property relationship for our hydrazide-based oligomers was depicted, which would provide guidelines for the design of hydrazide-based fine-tuning functional materials.