2,6-bis-(3-nitrobenzylidene)cyclopentanone | 273724-34-8

• 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: 2,6-bis-(3-nitrobenzylidene)cyclopentanone
• 英文别名: 2,5-bis(3-nitrobenzylidene)cyclopentanone；1.3-Bis-(3-nitro-benzal)-cyclopentanon-(2)；2,5-Bis-(3-nitro-benzyliden)-cyclopentanon；Cyclopentanone, 2,5-bis[(3-nitrophenyl)methylene]-；2,5-bis[(3-nitrophenyl)methylidene]cyclopentan-1-one
• CAS: 273724-34-8
• 化学式: C₁₉H₁₄N₂O₅
• 分子量: 350.331
• InChiKey: KTEWMZVMTXIQMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis-(3-nitrobenzylidene)cyclopentanone 在 氯仿 、 溴 作用下， 生成 2,5-dibromo-2,5-bis-(α-bromo-3-nitro-benzyl)-cyclopentanone
  参考文献：
  名称：

  Mentzel, Chemische Berichte, 1903, vol. 36, p. 1502

  摘要：

  DOI：
• 作为产物：
  描述：

  间硝基苯甲醛 、 环戊酮 在 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride 作用下， 反应 3.0h， 以86%的产率得到2,6-bis-(3-nitrobenzylidene)cyclopentanone
  参考文献：
  名称：

  1-甲基-3(2-(磺氧基)乙基)-1H-咪唑-3-鎓氯化物催化α,α'-双(取代-亚苄基)环烷酮的合成及荧光性质

  摘要：

  在催化量的 1-甲基-3(2-(磺氧基)乙基)-1H 存在下，通过芳香醛与环烷酮的无溶剂交叉羟醛缩合反应合成了 α,α'-双（取代亚苄基）环烷酮-咪唑-3-氯化鎓在室温下以优异的收率。光学性质的筛选表明，环烷酮的大小对产物的荧光发射有影响。来自环己酮的产物比来自环戊酮的产物具有更强的荧光发射。

  DOI：

  10.1080/00397910903243781

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。
• Green, rapid, and highly efficient syntheses of <i>α</i> , <i>α′</i> ‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones as potentially biologic compounds via solvent‐free microwave‐assisted Claisen–Schmidt condensation catalyzed by MoCl ₅
  作者：Reza Bakhshi、Behzad Zeynizadeh、Hossein Mousavi

  DOI：10.1002/jccs.201900081

  日期：2020.4

  A new, green, and highly efficient protocol for the expeditious preparation of some α,α′‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones via a simple microwave‐assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent‐free conditions, simple operation, use of

  一种新的，绿色的，高效的方法，可通过简单的微波快速制备某些α，α'-双[（芳基或烯丙基）亚烷基]环烷酮和2 [[（芳基或烯丙基）亚烷基] -1-茚满酮MoCl 5催化的克莱森-施密特辅助缩合反应开发成功。当前方法的突出特点包括：使用无溶剂条件，操作简单，使用非常便宜和可用的催化剂，催化剂用量低，反应时间短，纯产物的收率高，无有害副产物，易于后处理以及微波辐射作为清洁能源的适用性。此外，成功进行了克级反应，证明了当前Claisen-Schmidt缩合反应的可扩展性。
• 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。
• Condensation of 2,6-diarylmethylidenecyclohexa(penta)nones with acetylacetone and ethyl acetoacetate
  作者：T. V. Gulai、A. A. Morozova、A. G. Golikov

  DOI：10.1134/s1070428011110066

  日期：2011.11

  The reactions of symmetrically built diarylmethylidenecyclanones with ethyl acetoacetate and acetylacetone afforded products of carbo- and heterocyclization: hydronaphthalene(indan)ones, cyclopentapyrans, and hexahydrochromenes. The direction of the reaction depends on the size of the ring (C5, C6) of the diarylmethylidenecyclanones; the introduction of the electron-withdrawing nitro group into the

  对称构建的二芳基亚甲基亚环戊酮与乙酰乙酸乙酯和乙酰丙酮的反应提供了碳环和杂环化的产物：氢萘（茚满）酮，环戊二酮和六氢苯并二氢吡喃。反应的方向取决于二芳基亚甲基亚环环酮的环（C 5，C 6）的大小；将吸电子的硝基引入二芳基亚甲基取代基中提供了进行目标反应产生O-杂环化产物的可能性。
• Solvent-Free, Cross-Aldol Condensation Reaction Using Silica-Supported, Phosphorus-Containing Reagents Leading to α,α′-Bis(arylidene)cycloalkanones
  作者：Alireza Hasaninejad、Abdolkarim Zare、Laleh Balooty、Hadis Mehregan、Mohsen Shekouhy

  DOI：10.1080/00397910903457282

  日期：2010.11.3

  This article describes an efficient, simple, and clean method for the synthesis of alpha,alpha'-bis(arylidene, furylidene and cinnamylidene)cycloalkanones under solvent-free conditions. The cross-aldol condensation of cycloalkanones with aldehydes in the presence of silica-supported phosphorus pentoxide (P2O5/SiO2) or silicaphosphinoxide (silphox, [POCl3-n-(SiO2)(n)]) as heterogeneous reagents produces the title compounds in good to excellent yields.