2,6-bis(4-benzyloxyphenylmethylene)cyclohexanone | 146736-63-2

• 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-benzyloxyphenylmethylene)cyclohexanone
• 英文别名: (2E,6E)-2,6-bis[4-(benzyloxy)benzylidene]cyclohexanone；(2E,6E)-2,6-bis[(4-phenylmethoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 146736-63-2
• 化学式: C₃₄H₃₀O₃
• 分子量: 486.61
• InChiKey: CFPVWXYVGJLKGF-WECXDZCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-benzyloxyphenylmethylene)cyclohexanone 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以44%的产率得到2-[(4-Benzyloxy-phenyl)-hydroxyamino-methyl]-6-[1-(4-benzyloxy-phenyl)-meth-(E)-ylidene]-cyclohexanone oxime
  参考文献：
  名称：

  一些6-亚芳基-2-（α-羟基氨基-α-芳基甲基）环己酮肟及其相关化合物的合成和细胞毒性评估。

  摘要：

  2，6-双-（苯基亚甲基）环己酮（1）与4摩尔过量的羟胺盐酸盐和乙酸钠反应生成相应的肟2，生成2-（α-羟基氨基-α-苯基甲基）-6-苯基亚甲基环己酮一肟（5a），其结构由高分辨率质子核磁共振波谱推导，并通过X射线分析证实。最终由1与羟胺本身而不是由盐酸羟胺和乙酸钠的混合物制备化合物2。制备了10a的5a类似物，即5b-5k，并评估了细胞毒性。第5系列和11系列的11种化合物中有6种在240-950 microM范围内具有抗鼠乳腺EMT6细胞的活性。

  DOI：

  10.1002/jps.2600811103
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 环己酮 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以86%的产率得到2,6-bis(4-benzyloxyphenylmethylene)cyclohexanone
  参考文献：
  名称：

  A facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations

  摘要：

  An economical and facile synthesis of alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanones was achieved by the reaction of cycloalkanones with different aromatic aldehydes using ethanolic KOH in good yields. Few of the selected compounds were reduced with NaBH4 to the respective alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanols. All these compounds and our earlier synthesized cyclohexyl phenyl methanols were evaluated for their antitubercular, antifungal and antibacterial activities. Several compounds displayed moderate antitubercular activity with MIC = 12.5-1.56 mu g/mL. However, none of the compounds displayed any significant antifungal activity. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.026

文献信息

• A facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations
  作者：Nimisha Singh、Jyoti Pandey、Amit Yadav、Vinita Chaturvedi、Shalini Bhatnagar、Anil N. Gaikwad、Sudhir Kumar Sinha、Awaneet Kumar、P.K. Shukla、Rama P. Tripathi

  DOI：10.1016/j.ejmech.2008.09.026

  日期：2009.4

  An economical and facile synthesis of alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanones was achieved by the reaction of cycloalkanones with different aromatic aldehydes using ethanolic KOH in good yields. Few of the selected compounds were reduced with NaBH4 to the respective alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanols. All these compounds and our earlier synthesized cyclohexyl phenyl methanols were evaluated for their antitubercular, antifungal and antibacterial activities. Several compounds displayed moderate antitubercular activity with MIC = 12.5-1.56 mu g/mL. However, none of the compounds displayed any significant antifungal activity. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis and Cytotoxic Evaluation of Some 6-Arylidene-2-(α-hydroxyamino-α-arylmethyl)cyclohexanone Oximes and Related Compounds
  作者：J.R. Dimmock、K.K. Sidhu、J.W. Quail、Z. Jia、M.J. Duffy、R.S. Reid、D.L. Kirkpatrick、L. Zhu、S.M. Fletcher

  DOI：10.1002/jps.2600811103

  日期：1992.11

  hydroxylamine hydrochloride and sodium acetate. Ten analogues of 5a, namely 5b-5k, were prepared and evaluated for cytotoxicity. Six of the 11 compounds in series 5, as well as 1, showed activity in the 240-950 microM range against murine mammary EMT6 cells. Series 5 was also examined for cytotoxicity in an in vitro screen conducted by the National Cancer Institute with approximately 54 cell lines, and

  2，6-双-（苯基亚甲基）环己酮（1）与4摩尔过量的羟胺盐酸盐和乙酸钠反应生成相应的肟2，生成2-（α-羟基氨基-α-苯基甲基）-6-苯基亚甲基环己酮一肟（5a），其结构由高分辨率质子核磁共振波谱推导，并通过X射线分析证实。最终由1与羟胺本身而不是由盐酸羟胺和乙酸钠的混合物制备化合物2。制备了10a的5a类似物，即5b-5k，并评估了细胞毒性。第5系列和11系列的11种化合物中有6种在240-950 microM范围内具有抗鼠乳腺EMT6细胞的活性。