(E)-2-(4-nitrobenzylidene)cyclopentanone | 847062-95-7

• 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: (E)-2-(4-nitrobenzylidene)cyclopentanone
• 英文别名: 2-(4-nitrophenylmethylene)cyclopentanone；(2E)-2-[(4-nitrophenyl)methylidene]cyclopentan-1-one
• CAS: 847062-95-7
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: PFSPXVYIKPTEGN-CSKARUKUSA-N

物化性质

• 熔点：
  138 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  371.6±31.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲基苯甲醛 、 (E)-2-(4-nitrobenzylidene)cyclopentanone 生成 2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-5-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-cyclopentanone
  参考文献：
  名称：

  3-Arylidene-1-(4-nitrophenylmethylene)-3,4-dihydro-1H-naphthalen-2-ones and related compounds displaying selective toxicity and reversal of multidrug resistance in neoplastic cells

  摘要：

  The incorporation of the 1-aryl-5-(4-nitrophenyl)-3-oxo-1,4-pentadienyl group into 3,4-dihydro-1H-naphthalenyl, cyclohexyl, 2,3-dihydro-1H-indenyl and cyclopentyl scaffolds led to the discovery of various compounds with selective toxicity for malignant cells and ability to reverse multidrug resistance. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.054
• 作为产物：
  描述：

  对硝基苯甲醇 在 Nafion-TMS 、 polymer supported perruthenate 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (E)-2-(4-nitrobenzylidene)cyclopentanone
  参考文献：
  名称：

  Haunert, Frank; Bolli, Martin H.; Hinzen, Berthold, Journal of the Chemical Society. Perkin transactions I, 1998, # 15, p. 2235 - 2237

  摘要：

  DOI：

文献信息

• [EN] ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS<br/>[FR] ORGANOCATALYSEURS ET PROCEDES D'UTILISATION DE CES DERNIERS DANS LA SYNTHESE CHIMIQUE
  申请人：STC UNM

  公开号：WO2006007586A1

  公开（公告）日：2006-01-19

  The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo-­selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R', NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1­C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ('hydrocarbyl') group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R' are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R' form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R' are attached; and wherein said compound is free from a metal catalyst.

  本发明涉及一般包括有机催化剂的组合物，该催化剂促进立体选择性反应以及其合成和使用方法。特别地，本发明涉及无金属有机催化剂以促进立体选择性反应，以及其合成和使用方法。这些化合物具有以下结构的式（I）和（II）。其中X独立地选择自CH2、N-Ra、O、S或C=O；Y为CH2、N-Ra、O、S或C=O，但至少X或Y中的一个为CH2，最好是X和Y都为CH2；Ra为H、可选择地取代的C1-C12烷基，最好是可选择地取代的C1-C6烷基，包括C3-C6环烷基，或可选择地取代的芳基，最好是可选择地取代的苯基；Rb为H、可选择地取代的C1-C12烷基，最好是可选择地取代的C1-C6无环或C3-C6环烷基，CHO、N(Me)O、CO(S)Ra或式（III）的基团。其中Rc和Rd各自独立地为H、F、C1、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C12烷基，更好地是C1-C6烷基，以及可选择地取代的芳基，或者Rc和Rd一起形成可选择地取代的碳环或可选择地取代的杂环；R1为OH、OR、NR'R'、NHC(=O)R、NHSO2R；R2为H、F、C1、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，可选择地取代的芳基或=O基团（与=O连接的碳形成羰基基团）；R3为H、OH、F、C1、Br、I、Cl、可选择地取代的C1-C20烷基、烯基或炔基（'烃基'），最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基，使得R3连接的碳具有R或S构型；R为H、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基，R'和R'各自独立地为H、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基；或者R'和R'一起形成可选择地取代的杂环，最好是4到7成员的可选择地取代的杂环基团或与R'和R'连接的氮原子形成可选择地取代的杂芳基环；其中所述化合物不含金属催化剂。
• A Novel Pyrrolidine Imide Catalyzed Direct Formation of α,β-Unsaturated Ketones from Unmodified Ketones and Aldehydes
  作者：Wei Wang、Yujiang Mei、Hao Li、Jian Wang

  DOI：10.1021/ol047630g

  日期：2005.2.1

  (E)-alpha,beta-unsaturated ketones from ketones and aldehydes, promoted by a novel pyrrolidine imide organocatalyst, has been developed in moderate to high yields. Unlike the Claisen-Schmidt condensation and Lewis acid catalyzed tandem aldol-dehydration processes, this method provides mild reaction conditions to access alpha,beta-unsaturated ketones from simple, unmodified ketones. [reaction: see text]

  由酮和醛直接，立体选择性地制备（E）-α，β-不饱和酮的方法，由新型吡咯烷酰亚胺有机催化剂促进，已经以中等至高收率开发。与Claisen-Schmidt缩合反应和Lewis酸催化的串联醛醇缩合脱水过程不同，此方法提供了温和的反应条件，可从简单的未改性酮中获得α，β-不饱和酮。[反应：看文字]
• Bovine serum albumin-catalysed cross aldol condensation: Influence of ketone structure
  作者：Sebastián M. Ardanaz、Estefanía L. Borucki、Ana J. Velez Rueda、Gustavo Parisi、Adolfo M. Iribarren、Luis E. Iglesias

  DOI：10.1016/j.procbio.2019.08.003

  日期：2019.11

  Abstract Bovine serum albumin (BSA) catalyses the cross aldol condensation and proved to be catalytically active at mild temperature and in ethanol, a cheap and green solvent, contrasting with the strong or expensive reaction media usually employed for this reaction. We herein report the reaction of a set of ketones (butanone, 3-pentanone, cyclopentanone and cyclohexanone) with benzaldehyde and p-nitrobenzaldehyde

  摘要 牛血清白蛋白 (BSA) 催化交叉羟醛缩合，并被证明在温和的温度和乙醇（一种廉价的绿色溶剂）中具有催化活性，与通常用于该反应的强或昂贵反应介质形成对比。我们在此报告了一组酮（丁酮、3-戊酮、环戊酮和环己酮）与苯甲醛和对硝基苯甲醛的反应，这些反应提供了相应烯酮的高转化率（77-95%）（从 19 % 到 74%）。为实现这些转化值而测定的参数是溶剂、酮/醛摩尔比和温度。在该程序中，即使在苯甲醛/环己酮摩尔过量高的情况下，也仅环己酮产生少量双烯酮，即常规羟醛缩合的副产物。在所分析的条件下，除了环戊酮和对硝基苯甲醛的反应外，观察到酮醇的量为零或很低。此外，BSA 催化的环己酮和对硝基苯甲醛醛醇缩合的动力学数据表明烯酮形成的有序双双机制；还提出了一种涉及表现出异常 pKa 值的催化腔残基的烯胺机制。
• Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes
  作者：Xin Gu、Xiaoyan Wang、Fengtian Wang、Hongbao Sun、Jie Liu、Yongmei Xie、Mingli Xiang

  DOI：10.3390/molecules19021976

  日期：——

  An efficient method for the facile synthesis of (E)-monoarylidene derivatives of homo- and heterocyclic ketones with various aldehydes in the presence of a pyrrolidine organocatalyst has been achieved. A range of α,β-unsaturated ketones were obtained in moderate to high yields (up to 99%). Unlike the Claisen-Schmidt condensation process, the formation of undesired bisarylidene byproducts is not observed. The possible reaction mechanism suggests that the reaction proceeds via a Mannich-elimination sequence.

  在吡咯烷有机催化剂的作用下，实现了一种高效的方法，可以方便地合成同环酮和杂环酮与各种醛的 (E)- 单芳基衍生物。一系列 α、β-不饱和酮以中等至高产率（高达 99%）获得。与 Claisen-Schmidt 缩合过程不同的是，没有观察到不需要的双亚芳基副产物的形成。可能的反应机理表明，反应是通过曼尼希-消除顺序进行的。
• Fe₃O₄ Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of <font>α</font>,<font>β</font>-Unsaturated Heterocyclic and Cyclic Ketones under Solvent-Free Conditions
  作者：Tooba Alishiri、Hossein A. Oskooei、Majid M. Heravi

  DOI：10.1080/00397911.2013.786089

  日期：2013.12.17

  Abstract An efficient and green procedure has been developed for the synthesis of monoarylidenes of cyclic and heterocyclic ketones. The reaction was carried out under solvent-free conditions in the presence of a catalytic amount of nanosized magnetite (Fe3O4). The catalyst was easily removed by using an external magnet. The structures of the products were deduced from their 1H NMR, 13C NMR, and infrared

  摘要 开发了一种高效、绿色的合成环和杂环酮单芳基的方法。该反应在无溶剂条件下在催化量的纳米磁铁矿 (Fe3O4) 存在下进行。使用外部磁铁可以轻松去除催化剂。产物的结构由它们的 1H NMR、13C NMR、红外光谱和质谱推断。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要