1,1'-butane-1,4-diylbis-1H-indole-3-carbaldehyde | 676244-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,1'-butane-1,4-diylbis-1H-indole-3-carbaldehyde
• 英文别名: 1,4-di(3-formylindol-1-yl)butane；1,1'-butane-1,4-diylbis(1H-indole-3-carbaldehyde)；1-[4-(3-formylindol-1-yl)butyl]indole-3-carbaldehyde
• CAS: 676244-31-8
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: XFEHFUQYNZVPII-UHFFFAOYSA-N

物化性质

• 沸点：
  598.9±35.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-butane-1,4-diylbis-1H-indole-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以78%的产率得到1,1'-butane-1,4-diylbis-1H-indole-3-methanol
  参考文献：
  名称：

  评价合成大环双吲哚基马来酰亚胺的替代方法。

  摘要：

  描述了用于合成大环双吲哚基马来酰亚胺的方法，其中吲哚氮与系链连接。研究了两种替代方法：在“南部”（通过将系链添加到双辛基马来酰亚胺环系统中）或“北部”区域中的大环化。使用二原子，三原子和四原子的束缚链，这两种方法都无法成功地进行各种尝试的大环化反应（钯催化的π-烯丙基取代，闭环易位，McMurry反应，碘环化，形成亚甲硅烷基衍生物） （α，ω-二取代亲电试剂的取代）。所有这些反应的失败归因于靶环系统的应变性质。但是，如果使用更长的系链（6到10个原子），可以使用闭环复分解反应或通过α，ω-二溴化物的取代来制备大环化合物。描述了十四个成功的大环化反应。脱保护得到11个大环的双吲哚基马来酰亚胺，其中酰亚胺取代基已被除去。

  DOI：

  10.1039/b405010j
• 作为产物：
  描述：

  吲哚 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1,1'-butane-1,4-diylbis-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  评价合成大环双吲哚基马来酰亚胺的替代方法。

  摘要：

  描述了用于合成大环双吲哚基马来酰亚胺的方法，其中吲哚氮与系链连接。研究了两种替代方法：在“南部”（通过将系链添加到双辛基马来酰亚胺环系统中）或“北部”区域中的大环化。使用二原子，三原子和四原子的束缚链，这两种方法都无法成功地进行各种尝试的大环化反应（钯催化的π-烯丙基取代，闭环易位，McMurry反应，碘环化，形成亚甲硅烷基衍生物） （α，ω-二取代亲电试剂的取代）。所有这些反应的失败归因于靶环系统的应变性质。但是，如果使用更长的系链（6到10个原子），可以使用闭环复分解反应或通过α，ω-二溴化物的取代来制备大环化合物。描述了十四个成功的大环化反应。脱保护得到11个大环的双吲哚基马来酰亚胺，其中酰亚胺取代基已被除去。

  DOI：

  10.1039/b405010j

文献信息

• One-pot multicomponent synthesis of indol-3-yl-hydrazinyl thiazoles as antimicrobial agents
  作者：Nosrat O. Mahmoodi、Behzad Khalili、Olia Rezaeianzade、Atefeh Ghavidast

  DOI：10.1007/s11164-016-2478-y

  日期：2016.8

  were efficiently synthesized via one-pot cyclocondensation of mono- or bis(indole-3-carbaldehyde), thiosemicarbazide, and phenacyl bromides. The structure of the products was confirmed by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra. All synthesized compounds were evaluated for in vitro antibacterial activity against Gram-positive (Bacillus subtilis and

  通过单或双（吲哚-3-甲醛），硫代氨基脲和苯甲酰基溴的一锅环缩合，有效地合成了一系列新颖的单和双（吲哚-3-基）肼基噻唑衍生物。产物的结构通过傅里叶变换红外（FT-IR），1 H核磁共振（NMR）和13 C NMR光谱确认。评价所有合成的化合物对革兰氏阳性菌（枯草芽孢杆菌和琵琶微球菌）和革兰氏阴性菌（铜绿假单胞菌和沙门氏菌肠炎）的体外抗菌活性。）。在筛选出的化合物中，发现有少数是高效的抗菌剂。具有OCH 3给予基团的双化合物对革兰氏阳性细菌表现出良好的活性。
• One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole Derivatives Using Zn²⁺@KSF and Their Antibacterial Activity
  作者：Nosrat O. Mahmoodi、Iraj Nikokar、Marzieh Farhadi、Atefeh Ghavidast

  DOI：10.5560/znb.2014-4026

  日期：2014.6.1

  bis-indolylimidazole derivatives using Zn2+ supported on montmorillonite KSF (Zn2+@KSF) as an efficient heterogeneous catalyst is described. The structures of these compounds were characterized by IR, 1H NMR and 13C NMR spectroscopy. The antibacterial activity of the selected products was examined. Some products exhibit promising activities. Graphical Abstract One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole

  描述了使用负载在蒙脱石 KSF (Zn2+@KSF) 上的 Zn2+ 作为有效的多相催化剂制备单和双吲哚基咪唑衍生物。这些化合物的结构通过IR、1H NMR和13C NMR光谱表征。检查所选产品的抗菌活性。一些产品表现出有希望的活性。图解摘要 使用 Zn2+@KSF 的单和双吲哚咪唑衍生物的一锅多组分合成及其抗菌活性
• One-Pot Synthesis and Characterization of Some New Types of 5,5′-Disubstituted Bis(imidazolidine-2,4-diones)
  作者：Ziba Khodaee、Asieh Yahyazadeh、Nosrat O. Mahmoodi

  DOI：10.1002/jhet.1034

  日期：2013.3

  The synthesis and structural elucidation of some novel 5,5′‐disubstituted spiro and nonspiro‐bis‐hydantoins are reported. The Bucherer Burge's method has been modified for the preparation of some 5,5′‐substituted bis(imidazolidine‐2,4‐dione) derivatives starting with diketones (1–5) and dialdehydes (6, 7). In some cases, diastereoisomeric mixtures of compounds were obtained. The resulting bis‐hydantoins

  报道了一些新颖的5,5'-双取代螺和非螺-双-乙内酰脲的合成和结构解析。该布赫尔比尔格的方法已被修改为一些5,5'-取代的双（咪唑烷-2,4-二酮）开始二酮（衍生物的制备1-5）和二醛（6，7）。在某些情况下，获得化合物的非对映异构体混合物。得到的双乙内酰脲（8-11，13，14）都没有就我们所知，在文献中报道过。
• Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent
  作者：Palwinder Singh、Jagroop Kaur、Gurjit Singh、Rajbir Bhatti

  DOI：10.1021/acs.jmedchem.5b00952

  日期：2015.8.13

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.
• Twin compounds of phenylethenyl substituted indole as efficient materials for electroluminescent devices
  作者：D. Sipaviciute、D. Tavgeniene、G. Krucaite、J.V. Grazulevicius、D. Volyniuk、B. Yao、Z. Xie、B. Zhang、S. Grigalevicius

  DOI：10.1016/j.dyepig.2016.06.042

  日期：2016.11

  Twin compounds containing two phenylethenyl substituted indole rings were synthesized by a short multi-step synthetic route. The derivatives were characterized by thermo-gravimetric analysis, differential scanning calorimetry and electron photoemission technique. The materials were found to show very high thermal stability having initial thermal degradation temperatures in the range of 385-390 degrees C. Glass transition temperatures of the amorphous molecular materials were in the rage of 62-95 degrees C. The electron photoemission spectra of thin layers of the derivatives showed ionization potentials in the range of 5.4-5.5 eV. Hole drift mobilities in thin layers of these derivatives exceed 6.4 x 10(-5) cm(2)V(-1)s(-1) at high electric fields at room temperature. These materials have been tested as hole transporting layers in electroluminescent bilayer OLEDs with Alga as the emitter. The device with hole transporting layer comprised of 1,4-di[3-(2-phenylethenypindo1-1-yl]butane exhibited the best overall performance with low turn-on voltage of 3.4 V, a maximum luminance efficiency of 3 cd/A and maximum brightness of about 1400 cd/m(2). (C) 2016 Elsevier Ltd. All rights reserved.