3-chlorobenzaldehyde N-[-(3-chlorophenyl)methylidene]hydrazone | 41097-39-6

• 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: 3-chlorobenzaldehyde N-[-(3-chlorophenyl)methylidene]hydrazone
• 英文别名: N,N'-bis(3-chlorobenzylidene)hydrazine；1,2-bis(3-chlorobenzylidene)hydrazine；3,3'-dichlorobenzaldazine；DCB；bis-(3-chloro-benzylidene)-hydrazine；Bis-(3-chlor-benzyliden)-hydrazin；1-(3-chlorophenyl)-N-[(3-chlorophenyl)methylideneamino]methanimine
• CAS: 41097-39-6；6971-97-7
• 化学式: C₁₄H₁₀Cl₂N₂
• 分子量: 277.153
• InChiKey: XMOVWXSCYLINBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  40 °C
• 沸点：
  387.8±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：~6.8 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chlorobenzaldehyde N-[-(3-chlorophenyl)methylidene]hydrazone 在 碘苯二乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以77%的产率得到3-氯苯甲酸
  参考文献：
  名称：

  使用二乙酸碘苯合成吖嗪及其氧化降解为羧酸

  摘要：

  摘要 3-hydrazonobutan-2-one 肟与芳香醛的反应导致形成 1,2-双（亚芳基）肼，通常称为吖嗪，作为一种意想不到的产物，而不是预期的产物 3-（芳基）亚甲基肼基丁-2-一种肟，随后被一种环保的氧化剂碘苯二乙酸盐氧化成相应的芳香酸。肼和羧酸通过 IR 和 NMR（1H、13C、HMBC 和 HMQC）研究进行表征。图形概要

  DOI：

  10.1080/00397911.2017.1407791
• 作为产物：
  描述：

  3-氯苯腈 在 乙醇 、 镍 、 一水合肼 作用下， 生成 3-chlorobenzaldehyde N-[-(3-chlorophenyl)methylidene]hydrazone
  参考文献：
  名称：

  Pietra; Trinchera, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1045,1050

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-甲基苯硼酸 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 3-chlorobenzaldehyde N-[-(3-chlorophenyl)methylidene]hydrazone 、 sodium hydride 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 26.0h， 生成 5-(bromomethyl)-2-methoxy-9-(phenylsulfonyl)-9H-carbazole
  参考文献：
  名称：

  Ferulic acid–carbazole hybrid compounds: Combination of cholinesterase inhibition, antioxidant and neuroprotection as multifunctional anti-Alzheimer agents

  摘要：

  In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9 mu M) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture. (c) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.01.010

文献信息

• Easily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
  作者：Kun Xu、Xin Zheng、Zhiyong Wang、Xumu Zhang

  DOI：10.1002/chem.201304684

  日期：2014.4.7

  An efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand 1 c in the highly selective AHF of

  已经报道了一种有效的方法，该方法可合成用于不对称加氢甲酰化（AHF）的易于调节且空间庞大的配体的小文库。已测试了五组烯烃底物，具有优异的转化率，中等至出色的区域选择性和对映选择性。在所报道文献的最佳结果中，将配体1c应用于具有挑战性的底物2,5-二氢呋喃的高选择性AHF中，产生了几乎一种异构体，转化率高达99％，对映体过量（ee）高达92％ 。使用相同的配体可实现二氢吡咯底物的高度对映选择性AHF，ee高达95％  ，β-异构体/α-异构体比率高达> 1:50。
• A Family of Highly Selective Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5
  作者：Julie A. O'Brien、Wei Lemaire、Tsing-Bau Chen、Raymond S. L. Chang、Marlene A. Jacobson、Sookhee N. Ha、Craig W. Lindsley、Hervé J. Schaffhauser、Cyrille Sur、Douglas J. Pettibone、P. Jeffrey Conn、David L. Williams

  DOI：10.1124/mol.64.3.731

  日期：2003.9

  We have identified a family of highly selective allosteric modulators of the group I metabotropic glutamate receptor subtype 5 (mGluR5). This family of closely related analogs exerts a spectrum of effects, ranging from positive to negative allosteric modulation, and includes compounds that do not themselves modulate mGluR5 agonist activity but rather prevent other family members from exerting their modulatory effects. 3,3′-Difluorobenzaldazine (DFB) has no agonist activity, but it acts as a selective positive allosteric modulator of human and rat mGluR5. DFB potentiates threshold responses to glutamate, quisqualate, and 3,5-dihydroxyphenylglycine in fluorometric Ca2+ assays 3- to 6-fold, with EC50 values in the 2 to 5 μM range, and at 10 to 100 μM, it shifts mGluR5 agonist concentration-response curves approximately 2-fold to the left. The analog 3,3′-dimethoxybenzaldazine (DMeOB) acts as a negative modulator of mGluR5 agonist activity, with an IC50 of 3 μM in fluorometric Ca2+ assays, whereas the analog 3,3′-dichlorobenzaldazine (DCB) does not exert any apparent modulatory effect on mGluR5 activity. However, DCB seems to act as an allosteric ligand with neutral cooperativity, preventing the positive allosteric modulation of mGluRs by DFB as well as the negative modulatory effect of DMeOB. None of these analogs affects binding of [3H]quisqualate to the orthosteric (glutamate) site, but they do inhibit [3H]3-methoxy-5-(2-pyridinylethynyl)pyridine binding to the site for 2-methyl-6-(phenylethynyl)-pyridine, a previously identified negative allosteric modulator. With the use of these compounds, we provide evidence that allosteric sites on GPCRs can respond to closely related ligands with a range of pharmacological activities from positive to negative modulation as well as to neutral competition of this modulation.

  我们已鉴定出一类高度选择性的别构调节剂，用于I类代谢型谷氨酸受体亚型5（mGluR5）。这一类紧密相关的类化合物表现出了一系列效果，从正别构调节到负别构调节，并包括一些不直接调节mGluR5激动剂活性的化合物，而是防止其他家族成员发挥其调节作用。3,3′-二氟苯腈（DFB）没有激动剂活性，但作为人类和大鼠mGluR5的选择性正别构调节剂。DFB在荧光钙离子测定中能使谷氨酸、奎奎酸和3,5-二羟基苯基甘氨酸的阈值反应增强3到6倍，EC50值在2到5μM范围内，而在10到100μM时，它将mGluR5激动剂浓度-反应曲线向左移动约2倍。类化合物3,3′-二甲氧基苯腈（DMeOB）作为mGluR5激动剂活性的负调节剂，其IC50值为3μM，而类化合物3,3′-二氯苯腈（DCB）对mGluR5活性没有显著的调节效果。然而，DCB似乎作为具有中性协同性的别构配体，防止DFB对mGluRs的正别构调节以及DMeOB的负调节效应。这些类化合物均不影响[3H]奎奎酸与正位（谷氨酸）结合位点的结合，但它们确实抑制了[3H]3-甲氧基-5-(2-吡啶乙炔基)吡啶与2-甲基-6-(苯乙炔基)吡啶结合位点的结合，后者是一种已知的负别构调节剂。通过使用这些化合物，我们提供了证据表明GPCR上的别构位点能够对紧密相关的配体作出反应，这些配体具有从正调节到负调节以及对此调节的中性竞争等一系列药理活性。
• Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions
  作者：Zai-Gang Luo、Peng Liu、Yu-Yu Fang、Xue-Mei Xu、Cheng-Tao Feng、Zhong Li、Xiao-Mei Zhang、Jie He

  DOI：10.1007/s11164-016-2688-3

  日期：2017.2

  A facile, environmentally and efficient Cs2CO3-mediated decomposition of N-tosylhydrazones reaction has been developed for the synthesis of functionalized azines under mild conditions. This method offers broad substrate scope, occurs as additive-free, without strong base conditions, utilizes readily available reactants, and forms products in good to high yields.

  一种简便、环保且高效的Cs2CO3介导的N-对甲苯磺酰腙分解反应已在温和条件下开发出来，用于合成官能化的吖嗪。该方法具有广泛的底物适应性，不需添加额外物质，无需强碱条件，使用的反应物易得，并能在良好至高产率下形成产物。
• An efficient synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones catalyzed by TiO₂-functionalized nano-Fe₃O₄ encapsulated-silica particles as a reusable magnetic nanocatalyst
  作者：Javad Safari、Leila Javadian

  DOI：10.1039/c5ra23457c

  日期：——

  Immobilization of a nano-TiO2 catalyst on the surface of a magnetic SiO2 support was performed through the reaction of a Fe3O4@SiO2 composite with Ti(OC4H9)4 via a simple process. The Fe3O4@SiO2–TiO2 nanocomposite was characterized using scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), Fourier transform

  纳米的TiO固定2的磁性二氧化硅的表面上的催化剂2通过一个Fe的反应进行支撑3 ö 4 @SiO 2复合材料的Ti（OC 4 H ^ 9）4 经由一个简单的过程。利用扫描电子显微镜（SEM），透射电子显微镜（TEM），能量色散X射线光谱（EDS），X射线衍射（XRD），傅里叶变换红外光谱对Fe 3 O 4 @SiO 2 -TiO 2纳米复合材料进行表征。光谱（FTIR）和振动样品磁力计（VSM）。铁3 O 4已发现@SiO 2 -TiO 2纳米复合材料是从中合成过氢[1,2,4]三唑并[1,2- a ] [1,2,4]三唑-1,5-二硫酮的有效催化剂在室温下，各种乙二氮杂嗪和硫氰酸钾在乙腈溶剂中的缩合反应。已经发现，纳米催化剂被循环多达6个循环，而催化活性损失最小。这项研究的目的是提供一种简便的方法，通过一种坚固且可磁回收的催化剂来合成全氢三唑并三唑衍生物。
• New Synthesis of Perhydrotriazolotriazoles Catalyzed by TiCl₄under Ambient Conditions
  作者：J. Safari、S. Gandomi-Ravandi、M. Ghotbinejad

  DOI：10.5012/jkcs.2012.56.1.078

  日期：2012.2.20

  Aromatic 2,3-diazabuta-1,3-dienes in glacial acetic acid with isothiocyanate in the presence of catalyst $TiCl_4$ at room temperature produced via criss-cross cycloaddition reactions the corresponding perhydro[1,2,4]triazolo[1,2-a][1,2,4] triazole-1,5-dithiones in relatively high yields and short reaction time.

  在冰醋酸中，芳香族2,3-二氮杂丁烯-1,3-二烯与异硫氰酸盐在催化剂TiCl₄存在下于室温下通过交叉环加成反应生成相应的过氢[1,2,4]三唑[1,2-a][1,2,4]三唑-1,5-二硫酮，产率相对较高且反应时间较短。