2,6-Bis(naphthalen-2-ylmethylene)cyclohexanone | 62085-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-Bis(naphthalen-2-ylmethylene)cyclohexanone
• 英文别名: 2,6-bis(naphthalen-2-ylmethylidene)cyclohexan-1-one
• CAS: 62085-77-2；53376-39-9
• 化学式: C₂₈H₂₂O
• 分子量: 374.482
• InChiKey: ATBOLDOYGLNRHD-UHFFFAOYSA-N

物化性质

• 熔点：
  199-202 °C(Solv: ethanol (64-17-5))
• 沸点：
  625.7±55.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• 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：

  2,6-Bis(naphthalen-2-ylmethylene)cyclohexanone 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 73.5h， 生成 3-(β-naphthyl)-7-(β-naphthylidene)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbodithioic acid
  参考文献：
  名称：

  Kabli, R. A.; Kaddah, A. M.; Khalil, A. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 152 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 、 2-萘甲醛 在 sulfuric acid modified polyethylene glycol-6000 作用下， 以 neat (no solvent) 为溶剂， 反应 3.5h， 以82%的产率得到2,6-Bis(naphthalen-2-ylmethylene)cyclohexanone
  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。
• Synthesis, characterization, crystal structure of novel bis-thiomethylcyclohexanone derivatives and their inhibitory properties against some metabolic enzymes
  作者：Abdullah Biçer、Parham Taslimi、Gül Yakalı、Ilhami Gülçin、Mehmet Serdar Gültekin、Günseli Turgut Cin

  DOI：10.1016/j.bioorg.2018.11.001

  日期：2019.2

  synthesized by the addition of thio-Michael to the bis-chalcones under mild reaction conditions. The bis-thiomethylcyclohexanone derivatives (bis-sulfides) were characterized by 1H NMR, 13C NMR, FTIR and elemental analysis techniques. Furthermore, the molecular and crystal structures of 3h, 3i and 3j compounds were determined by single crystal X-ray diffraction studies. In this study, X-ray crystallography

  在这项研究中，通过在温和的反应条件下向双查耳酮中添加硫代迈克尔基，合成了一系列新型的双硫代甲基环己酮化合物（3a–3j）。通过1 H NMR，13 C NMR，FTIR和元素分析技术对双硫代甲基环己酮衍生物（双硫化物）进行了表征。此外，3h，3i和3j的分子和晶体结构通过单晶X射线衍射研究确定化合物。在这项研究中，X射线晶体学为阐明酶抑制位点上的官能团提供了一种替代性的且通常是补充性的手段。乙酰胆碱酯酶（AChE）是水解酶蛋白超家族的成员，在乙酰胆碱介导的神经传递中起重要作用。在这里，我们报告基于AChE抑制剂的新型双-硫代甲基环己酮化合物的混合支架的合成和确定。新合成的双硫代甲基环己酮化合物的K i抗人碳酸酐酶I同工酶（hCA I）的值分别为39.14–183.23 nM，抗人碳酸酐酶II同工酶（hCA II）的值分别为46.03–194.02 nM，抗AChE的4.55–32.64 nM和抗丁酰胆碱酯酶（BChE
• Cyclization of α,α′-bis(substituted-benzylidene)cyclohexanones and 4-hydroxycoumarin: synthesis of 11-benzylidene-8,9,10,11-tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chromen-6-ones as new pyranochromene derivatives
  作者：Gholam Hossein Mahdavinia、Somayyeh Peikarporsan

  DOI：10.1007/s00706-012-0845-y

  日期：2013.3

  A series of new 11-benzylidene-8,9,10,11-tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chromen-6-ones has been synthesized through a new Michael addition domino cyclization between alpha,alpha'-bis(substituted-benzylidene)cyclohexanones and 4-hydroxycoumarin in acetic acid at reflux conditions. Very good to excellent yields of the products, operational simplicity, and simple workup are attractive features of this synthesis protocol.
• Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents
  作者：Nimisha Singh、Sarvesh Kumar Pandey、Namrata Anand、Richa Dwivedi、Shyam Singh、Sudhir Kumar Sinha、Vinita Chaturvedi、Natasa Jaiswal、Arvind Kumar Srivastava、Priyanka Shah、M. Imran Siddiqui、Rama Pati Tripathi

  DOI：10.1016/j.bmcl.2011.06.040

  日期：2011.8

  An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydroquinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H(37)Rv strain and the a-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 mu g/mL against M. tuberculosis and very good inhibition of a-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 mu g/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• Amoozadeh, Ali; Rahmani, Salman; Nemati, Firouzeh, South African Journal of Chemistry, 2010, vol. 63, p. 72 - 74
  作者：Amoozadeh, Ali、Rahmani, Salman、Nemati, Firouzeh

  DOI：——

  日期：——