2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone | 19226-99-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone
• 英文别名: 2,2'-bis(4-dimethylaminobenzylidene)cyclopentanone；2,5-bis(4'-dimethylaminobenzylidene)cyclopentanone；2,5-bis-(4-dimethylamino-benzylidene)-cyclopentanone；1.3-Bis-(4-dimethylamino-benzal)-cyclopentanon-(2)；2,5-Bis-(4-dimethylamino-benzyliden)-cyclopentanon；2,5-bis(4-N,N-dimethylaminobenzylidene)cyclopentanone；2,5-Bis([4-(dimethylamino)phenyl]methylene)cyclopentanone；2,5-bis[[4-(dimethylamino)phenyl]methylidene]cyclopentan-1-one
• CAS: 19226-99-4
• 化学式: C₂₃H₂₆N₂O
• 分子量: 346.472
• InChiKey: GPXHIYXWGUYGHF-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C(Solv: ethanol (64-17-5))
• 沸点：
  561.7±50.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone 生成 2,5-bis(4-N,N-dimethylaminobenzylidene)cyclopentanium perchlorate
  参考文献：
  名称：

  Cycloalkene compounds useful in recording materials

  摘要：

  以下是一种新型环烯烃化合物的通式[1]：##STR1## 其中R1和R2分别为C1-C4烷基，R3为氢原子或C1-C4烷基，R4与R5一起形成--CH2--CH2--或--CH2--CH2--CH2--，R6为C1-C4烷基。

  公开号：

  US04987262A1
• 作为产物：
  描述：

  环戊酮 、 对二甲氨基苯甲醛 在 sulfuric acid modified polyethylene glycol-6000 作用下， 以 neat (no solvent) 为溶剂， 反应 3.5h， 以67%的产率得到2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone
  参考文献：
  名称：

  硫酸改性的PEG-6000（PEG-SO 3 H）：一种高效，可生物降解和可重复使用的合成αα，α'β的催化剂 无溶剂条件下的双（亚芳基）环烷酮

  摘要：

  一种绿色高效的合成α，α'??的方法 描述了一种双（亚芳基）环烷酮，它是在80℃无溶剂条件下，使用磺化聚乙二醇6000（PEG-SO 3 H）作为稳定，可重复使用和可生物降解的催化剂，从芳族醛与酮反应制得的。使用无毒，便宜，易于获得和可回收的催化剂使该方案切实可行，对环境友好并且在经济上具有吸引力。

  DOI：

  10.2174/1570178611310030004

文献信息

• Fast, Facile and Convenient Synthesis of<i>α,α</i>-Bis(substituted-arylidene) Cycloalkanones: An improved Protocol
  作者：Gholam Hossein Mahdavinia、Maryam Mirzazadeh

  DOI：10.1155/2012/390528

  日期：——

  Commercially available potassium hydroxide (KOH), a simple base, was found to be a catalyst for tandem cross-aldol condensation between cyclic ketones and aromatic aldehydes leading to a fast and easy synthesis ofα,α-bis (substituted-arylidene) cycloalkanones in the shortest times of all previous methods. The reaction of aryl aldehydes with five and six-membered cyclic ketones afforded excellent yields after few seconds in most cases. The reaction conditions were compatible with various electron withdrawing and electron donating substituents,e.g.Cl, F, NO₂, OMe, Me and NMe₂.

  商业上可获得的氢氧化钾（KOH），一种简单的碱，被发现是环状酮和芳香醛之间串联十字-醛缩合的催化剂，从而在所有先前方法中时间最短地合成α,α-双（取代芳基亚亚甲基）环戊酮。芳基醛与五元和六元环状酮的反应在大多数情况下在几秒钟后得到了优异的产率。反应条件与各种电子吸引和电子供体取代基兼容，e.g.Cl，F，NO₂，OMe，Me和NMe₂。
• Ash of pomegranate peels (APP): A bio-waste heterogeneous catalyst for sustainable synthesis of α,α′-bis(substituted benzylidine)cycloalkanones and 2-arylidene-1-tetralones
  作者：Rupesh C. Patil、Uttam P. Patil、Ashutosh A. Jagdale、Sachinkumar K. Shinde、Suresh S. Patil

  DOI：10.1007/s11164-020-04160-5

  日期：2020.7

  Abstract α,α′-bis(substituted benzylidene)cycloalkanones were efficiently prepared from variously substituted aldehydes and cycloalkanones in water by using ash of pomegranate peels (APP) as a catalyst. The APP-catalyst was obtained from bio-waste by simple thermal treatment to dry peels of pomegranate fruit and formation of its active phase was confirmed by FT-IR, XRD, XRF, EDX, SEM, DSC-TGA and BET

  摘要 以石榴皮（APP）的灰分为催化剂，由水中的各种取代的醛和环烷酮可高效制备α，α'-双（取代的亚苄基）环烷酮。通过简单的热处理将石榴果皮干燥即可从生物废料中获得APP催化剂，并通过FT-IR，XRD，XRF，EDX，SEM，DSC-TGA和BET技术证实了其活性相的形成。分析表明，本发明的催化剂具有促进所需产物合成的碱性位点。我们协议的主要吸引力是利用高度丰富的生物废物衍生催化剂，并在最短的反应时间内获得良好至优异的产率。通过在低温下将等摩尔量的芳族醛和1-四氢萘酮缩合，该绿色方案进一步扩展为结构上多样化的2-亚芳基-1-四氢萘酮。 图形摘要
• Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents
  作者：Nitesh Tamang、Gayathri Ramamoorthy、Mayank Joshi、Angshuman Roy Choudury、Siva Kumar B.、Nageswara Rao Golakoti、Mukesh Doble

  DOI：10.1007/s00044-020-02578-5

  日期：2020.9

  Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested

  癌症通常与慢性炎症有关。为了开发潜在的抗癌药和抗炎药，合成了26种二芳基亚环戊酮（DACP）Ia-Iv，II，III和IV。合成的DACP中有五个是新颖的（Ih，Ij，Ik，Is和Iv），使用单晶X射线衍射研究表征了衍生物Iv。测试所有合成的衍生物的抗炎和细胞毒性。复合是通过抑制PGE 2（前列腺素E 2）的产生，发现其具有最高的抗炎活性（93.67％）。观察到三个DACP s（Io，It和Iu）具有很高的细胞毒性，对HeLa的IC 50值分别为8.73±0.06 µM（Io），12.55±0.31 µM（It）和11.47±0.15 µM（Iu）细胞。使用这三个DACP进行了进一步的染色和细胞周期分析，以了解其作用机理。观察到G 0 / G 1相是细胞经历凋亡的最长相。
• Structural and photophysical properties of alkylamino substituted 2-arylidene and 2,5-diarylidene cyclopentanone dyes
  作者：Christopher A. Zoto、Mine G. Ucak-Astarlioglu、John C. MacDonald、Robert E. Connors

  DOI：10.1016/j.molstruc.2016.02.009

  日期：2016.5

  nature of the S 0 → S 1 excitation for these compounds, with higher degrees of ICT depicted for the alkylamino substituted 2,5-diarylidene cyclopentanones. Photophysical properties consisted of measuring the fluorescence quantum yields (Φ f ) and lifetimes (τ f ) in a variety of solvents. Radiative and nonradiative decay constants have been determined from the Φ f and τ f data. Variation with solvent in

  摘要 合成了一系列烷基氨基取代的2-亚芳基和2,5-二亚芳基环戊酮化合物。这些化合物的光谱和光物理特性已经在各种溶剂中进行了测量。吸收和荧光最大值与溶剂极性的经验标度 (ET (30)) 相关。理论 TD-DFT 光谱计算和 Lippert-Mataga 分析支持这些化合物的 S 0 → S 1 激发的内部电荷转移 (ICT) 性质，其中烷基氨基取代的 2,5-二亚芳基环戊酮具有更高程度的 ICT。光物理特性包括测量各种溶剂中的荧光量子产率 (Φ f ) 和寿命 (τ f )。辐射和非辐射衰减常数已根据 Φ f 和 τ f 数据确定。非辐射衰变率随溶剂的变化被解释为内部转换和系统间交叉之间的竞争。最后，已显示两种化合物在冰醋酸中经历激发态质子化。
• Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones
  作者：Saulo F.P. Braga、Érika V.P. Alves、Rafaela S. Ferreira、Jordana R.B. Fradico、Paula S. Lage、Mariana C. Duarte、Tatiana G. Ribeiro、Policarpo A.S. Júnior、Alvaro J. Romanha、Maiko L. Tonini、Mário Steindel、Eduardo F. Coelho、Renata B. de Oliveira

  DOI：10.1016/j.ejmech.2013.11.011

  日期：2014.1

  A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 mu M. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 mu M). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (<= 1.2 mu M) with an adequate SI (>= 19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain. (C) 2013 Elsevier Masson SAS. All rights reserved.