2,5-bis-(4-chloro-benzylidene)-cyclopentanone | 106115-45-1

• 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: 2,5-bis-(4-chloro-benzylidene)-cyclopentanone
• 英文别名: α,α'-bis(4-chlorobenzylidene)cyclopentanone；2,5-bis(4-chlorobenzylidene)cyclopentanone；2,5-di(p-chlorobenzylidene)cyclopentanone；1.3-Bis-(4-chlor-benzal)-cyclopentanon-(2)；2,5-Bis-(4-chlor-benzyliden)-cyclopentanon；2,5-Bis[(4-chlorophenyl)methylene]cyclopentanone；2,5-bis[(4-chlorophenyl)methylidene]cyclopentan-1-one
• CAS: 106115-45-1；42019-88-5
• 化学式: C₁₉H₁₄Cl₂O
• mdl: MFCD00121539
• 分子量: 329.226
• InChiKey: HOAWLEKLGGIUDF-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C(Solv: ethanol (64-17-5))
• 沸点：
  523.8±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-bis-(4-chloro-benzylidene)-cyclopentanone 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-amino-9-(4-chlorobenzylidene)-6-(4-chlorophenyl)-2-(methylthio)-6,7,8,9-tetrahydro-cyclopenta[d]pyrimido[1,2-a]pyrimidine-3-carbonitrile
  参考文献：
  名称：

  Synthesis and spectroscopic characterization of novel 2-amino-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidine and pyrimido[1,2-a]pyrimidine derivatives

  摘要：

  2-Aminocyclopenta[d]pyrimidines 3a-c were achieved via a one-pot, three-component reactions of cyclopentanone 1, aromatic aldehyde and guanidine hydrochloride (1:2:1 molar ratio). Also, cyclization of 2,5-bis-(arylmethylidene)cyclopentanones 2 with guanidine hydrochloride (1:1 molar ratio) in methanol in the presence of sodium methoxide afforded cyclopenta-[d]pyrimidines 3. Compound 3c has been shown to be a useful building block for the synthesis of some novel pyrimido[1,2-a]pyrimidines 5,7 and 12. The structures of the newly synthesized compounds were confirmed on the basis of analytical and spectral data. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.04.003
• 作为产物：
  描述：

  4-氯苯甲醛 、 环戊酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,5-bis-(4-chloro-benzylidene)-cyclopentanone
  参考文献：
  名称：

  Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes

  摘要：

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。

  DOI：

  10.1111/j.2042-7158.2011.01423.x

文献信息

• KF-Melamine Formaldehyde Resin (KF-MFR) as a Versatile and Efficient Heterogeneous Reagent for Aldol Condensation of Aldehydes and Ketones under Microwave Irradiation
  作者：Ramin Rezaie、Mohammad Heidary、Mohammad Navid Soltani Rad、Somayeh Behrouz

  DOI：10.1002/cjoc.201190227

  日期：2011.6

  KF‐Melamine formaldehyde resin (KF‐MFR) was demonstrated to be a highly efficient heterogenious catalyst for cross‐aldol condensation under microwave irradiation. In this synthesis, various aldehydes and ketones were condensed together in the presence of supported KF on melamine‐formaldehyde resin to afford different chalcone derivatives in good to excellent yields. KF‐MFR proved to have unique termal

  事实证明，KF-三聚氰胺甲醛树脂（KF-MFR）是微波辐射下交联醇醛缩合的高效多相催化剂。在该合成中，在三聚氰胺甲醛树脂上负载的KF的存在下，将各种醛和酮缩合在一起，从而以良好或优异的收率得到不同的查尔酮衍生物。事实证明，KF-MFR具有独特的耐热性和耐化学性，可以重复使用多次，而不会显着降低催化活性。
• Synthesis, characterization, and crystal structures of α, α′-bis(substituted-benzylidene)cycloalkanone derivatives by nano-TiO2/HOAc
  作者：Elham Tabrizian、Ali Amoozadeh、Salman Rahmani、Mehdi Salehi、Maciej Kubicki

  DOI：10.1007/s11164-015-2039-9

  日期：2016.2

  A new and economical synthesis of α, α′-bis(substituted-benzylidene)cycloalkanones has been achieved by the reaction of cycloalkanones with different aromatic aldehydes using nano-TiO2/acetic acid as a catalyst in ethanol under reflux conditions with excellent yields. Five new products and three new single crystal structures are reported.

  通过使用纳米TiO 2 /乙酸作为催化剂，在乙醇中回流条件下，环烷酮与不同的芳族醛反应，在乙醇中回流条件下，以优异的收率实现了一种新的，经济的α，α'-双（取代亚苄基）环烷酮的合成。报告了五种新产品和三种新的单晶结构。
• Nanomagnetic-supported Sulfonic Acid: Simple and Rapid Method for the Synthesis of<i>α</i>,<i>α′</i>-Bis-(substituted-benzylidene) Cycloalkanones
  作者：Ali Amoozadeh、Eskandar Kolvari、Nadiya Koukabi、Somayeh Otokesh

  DOI：10.1002/jccs.201400377

  日期：2015.6

  Nanomagnetic‐supported sulfonic acid is found to be a powerful and reusable heterogeneous catalyst for the rapid synthesis of α,α′‐bis‐(substituted‐benzylidene)cycloalkanones under conventional heating and solvent free conditions. High yield, simple work up and easy recovery of the catalyst are the most obvious advantages of this procedure.

  纳米磁性负载的磺酸是一种功能强大且可重复使用的异质催化剂，可在常规加热和无溶剂条件下快速合成α，α'-双-（取代亚苄基）环烷酮。高产率，简单的后处理和催化剂的容易回收是该方法的最明显的优点。
• 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。
• Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst
  作者：Li Q. Kang、Yue Q. Cai、Hao Wang、Li H. Li

  DOI：10.1007/s00706-013-1082-8

  日期：2014.2

  AbstractVarious 2,6-dibenzylidenecycloalkanones were readily prepared in a condensation reaction catalyzed by 2-hydroxyethylammonium acetate ionic liquid under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, lack of solvent, simplicity of performance, and low cost. Graphical abstract

  摘要在无溶剂条件下，由乙酸2-羟乙基铵离子液体催化的缩合反应中，很容易制得各种2,6-二亚苄基环烷酮。本方法的主要优点是产率高，反应时间短，溶剂少，性能简单和成本低。 图形概要