α,α'-bis(naphthalen-1-ylmethylene)cyclohexanone | 18977-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: α,α'-bis(naphthalen-1-ylmethylene)cyclohexanone
• 英文别名: 2,6-Bis(1-naphthalenylmethylene)cyclohexanone；2,6-bis(naphthalen-1-ylmethylidene)cyclohexan-1-one
• CAS: 18977-34-9
• 化学式: C₂₈H₂₂O
• mdl: MFCD03757233
• 分子量: 374.482
• InChiKey: RQLOEGRFORZSTA-UHFFFAOYSA-N

物化性质

• 熔点：
  208-209 °C(Solv: N,N-dimethylformamide (68-12-2))
• 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：

  α,α'-bis(naphthalen-1-ylmethylene)cyclohexanone 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以43%的产率得到2,6-Dibromo-2,6-bis-(bromo-naphthalen-1-yl-methyl)-cyclohexanone
  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 、 1-萘甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 α,α'-bis(naphthalen-1-ylmethylene)cyclohexanone
  参考文献：
  名称：

  Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.06.040

文献信息

• Chemoselective Claisen–Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster
  作者：Yufei Wu、Jie Hou、Yuliang Liu、Mingfu Zhang、Chen-Ho Tung、Yifeng Wang

  DOI：10.1016/j.tet.2016.01.055

  日期：2016.3

  The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen–Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity

  链烷酮的高效和化学选择性的α，α'-双取代在有机合成中很重要。在本文中，二聚物钛簇Ti 2 Cl 2（OPr i）6 ·2HOPr i（Ti 2）用于克莱森－施密特缩合反应，以选择性活化包含α，α'-亚甲基和高效和化学选择性生产α，α'-双取代链烷酮。高效和化学选择性可以扩展到各种典型的链烷酮和芳族醛。Ti 2的氧桥联二聚体基序 离子Ti-Cl键负责高效和化学选择性。
• Synthesis of diarylcyclopropyl spirocyclic ketones
  作者：Meng-Yang Chang、Chieh-Kai Chan、Yi-Chia Chen

  DOI：10.1016/j.tet.2014.02.056

  日期：2014.4

  A facile one-pot synthetic route for preparing a series of functionalized diarylcyclopropyl spirocyclic ketones 4 is developed. The efficient cyclopropanation route of the conjugated cyclic ketones 2 with sulfones 1 in the presence of NaH shows interesting molecular diversities. The reaction mechanism of the stereocontrolled cyclopropanations has been discussed. (C) 2014 Elsevier Ltd. All rights reserved.
• 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
  作者：Kabli, R. A.、Kaddah, A. M.、Khalil, A. M.、Khalaf, A. A.

  DOI：——

  日期：——
• 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.