2,6-bis(4-bromobenzylidene)cyclohexanone | 140422-06-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6-bis(4-bromobenzylidene)cyclohexanone
• 英文别名: Cyclohexanone, 2,6-bis[(4-bromophenyl)methylene]-, (E,E)-；2,6-bis[(4-bromophenyl)methylidene]cyclohexan-1-one
• CAS: 140422-06-6
• 化学式: C₂₀H₁₆Br₂O
• mdl: MFCD00489698
• 分子量: 432.154
• InChiKey: HXRSOYCNABLYMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2,6-bis(4-bromobenzylidene)cyclohexanone 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 0.02h， 以78%的产率得到7-(4-bromobenzylidene)-3-(4-bromophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole
  参考文献：
  名称：

  Microwave-Assisted In Situ Cyclization of Curcumin Derivatives as Dominant Chemotherapeutic Agents for Leukemia and Colon Cancer

  摘要：

  DOI：

  10.1134/s1070428022030150
• 作为产物：
  描述：

  环己醇 在 chromium(III) oxide 、 sodium hydroxide 、 硫酸 作用下， 生成 2,6-bis(4-bromobenzylidene)cyclohexanone
  参考文献：
  名称：

  Garland; Reid, Journal of the American Chemical Society, 1925, vol. 47, p. 2336

  摘要：

  DOI：

文献信息

• Catalyse heterogene par des sels et sans solvant
  作者：J. Boyer、R.J.P. Corriu、R. Perz、C. Reye

  DOI：10.1016/s0022-328x(00)83481-6

  日期：1980.1

  Addition with α,β unsaturated carbonyl compounds gives 1,5 dicarbonyl products. This method is very convenient and the compounds obtained can easily be separated. We assume that the role of the salt in these reactions is to activate the silicon atom by anionic coordination to form a pentacoordinated silicon intermediate.

  甲硅烷基烯醇醚与羰基化合物的反应通过非均相催化而活化。氟化铯是最好的催化剂。不饱和酮是通过使硅烷基烯醇醚与醛和酮缩合反应直接获得的。1,4与α，β不饱和羰基化合物加成，得到1,5二羰基产物。该方法非常方便，并且可以容易地分离得到的化合物。我们假设盐在这些反应中的作用是通过阴离子配位活化硅原子以形成五配位的硅中间体。
• 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。
• 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。
• Sulfuric Acid-modified PEG-6000 (PEG-SO&lt;sub&gt;3&lt;/sub&gt;H): An Efficient, Bio-degradable and Reusable Catalyst for Synthesis of &amp;alpha;, &amp;alpha;' bis(arylidene) Cycloalkanones Under Solvent-free Conditions
  作者：Mohammad A. Nasseri、Mehri Salimi

  DOI：10.2174/1570178611310030004

  日期：2013.4.1

  A green and efficient method for synthesis of α,α'  -bis (arylidene) cycloalkanones, starting from aromatic aldehydes in reaction with ketones using sulfonated polyethylene glycol 6000 (PEG-SO3H) as a stable, reusable and biodegradable catalyst under solvent-free conditions at 80 °C is described. The use of a nontoxic, inexpensive, easily available and recyclable catalyst makes this protocol practical

  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。
• An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water
  作者：A. Nakhaei、A. Morsali、A. Davoodnia

  DOI：10.1134/s1070363217050292

  日期：2017.5

  Aldol and cross-aldol condensations of aromatic aldehydes with various ketones in the presence of nanometasilica disulfuric acid (NMSDSA) as heterogeneous catalyst are presented. The catalyst was prepared according to the developed earlier method using inexpensive and readily available starting materials. The highly active catalyst gave excellent yields of the desired aldol products without self-condensation

  介绍了在作为非均相催化剂的纳米金属二硫酸（NMSDSA）存在下芳香醛与各种酮的醛醇缩合和交叉醛缩合。根据开发的较早方法，使用便宜且容易获得的起始原料制备催化剂。高活性催化剂在不发生自缩合反应的情况下得到所需醛醇产物的优异产率。反应时间短，步骤和后处理简单，不涉及挥发性或有害有机溶剂。催化剂可以被回收三次，而活性仅略有降低。