α,α'-bis(3,4-methylenedioxybenzylidene)cyclohexanone | 5216-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: α,α'-bis(3,4-methylenedioxybenzylidene)cyclohexanone
• 英文别名: (2E,6E)-2,6-bis(benzo[d][1,3]dioxol-5-ylmethylene)cyclohexanone；2,6-((E,E)-dipiperonylidene)-cyclohexanone；2,6-((E,E)-Dipiperonyliden)-cyclohexanon；(2E,6E)-2,6-bis(1,3-benzodioxol-5-ylmethylidene)cyclohexanone；(2E,6E)-2,6-bis(1,3-benzodioxol-5-ylmethylidene)cyclohexan-1-one
• CAS: 5216-82-0
• 化学式: C₂₂H₁₈O₅
• 分子量: 362.382
• InChiKey: FSKXKUGPSKOGHB-GONBZBRSSA-N

物化性质

• 熔点：
  187-188 °C
• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α,α'-bis(3,4-methylenedioxybenzylidene)cyclohexanone 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以48%的产率得到2-(Benzo[1,3]dioxol-5-yl-hydroxyamino-methyl)-6-[1-benzo[1,3]dioxol-5-yl-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：

  胡椒醛 、 环己酮 在 盐酸 作用下， 反应 11.0h， 以81%的产率得到α,α'-bis(3,4-methylenedioxybenzylidene)cyclohexanone
  参考文献：
  名称：

  对称和不对称取代的2,5-二亚芳基环己酮作为抗寄生虫化合物

  摘要：

  通过用各种醛处理环己酮，以中等至极好的收率合成了对称和不对称的双芳基-α，β-不饱和酮。二甲基氨基甲酸二甲基铵（DIMCARB）既用作催化剂，又用作反应介质，用于合成单亚芳基环加合物中间体，该中间体还用于生产二亚芳基环己酮。评估了所有34种合成化合物的抗增殖活性，特别是针对亚马逊利什曼原虫的前鞭毛体，克氏锥虫的前鞭毛体和锥鞭毛体。十八种化合物对L的前鞭毛体显示出抗利什曼活性。亚马逊IC 50值范围从2.8到10μM。另外，两种化合物表现出对的epimastigotes显著抗锥体虫活动锥虫带IC 50为5.2±0.8和3.0±0.0μM值，而五种化合物表现出的活性为15.0±1.4 30.2±1.8μM针对的锥鞭毛体克氏锥虫。而且，与上皮细胞相比，所有化合物对寄生虫的选择性更高。不对称化合物16，28，30和33可以被认为是具有IC有利抗寄生虫先导分子50和EC 50值在低微摩尔范围内，优于

  DOI：

  10.1016/j.ejmech.2018.06.031

文献信息

• A novel and efficient direct aldol condensation from ketones and aromatic aldehydes catalyzed by proline–TEA through a new pathway
  作者：Jun-feng Wang、Meng Lei、Qin Li、Ze-mei Ge、Xin Wang、Run-tao Li

  DOI：10.1016/j.tet.2009.04.052

  日期：2009.6

  aldol condensation from various ketones and a wide range of aldehydes was catalyzed by l-proline–TEA (triethylamine) in MeOH at room temperature, affording the corresponding (E)-α,β-unsaturated ketones in excellent yields. By using the method, some complicated (E)-α,β-unsaturated ketone C-glycosides were obtained from unmodified ketone C-glycosides and aldehydes. This reaction proceeds through a new

  在室温下于甲醇中，通过1-脯氨酸-TEA（三乙胺）催化从各种酮和多种醛中合成的新颖高效的直接羟醛缩合反应，从而以优异的收率得到相应的（E）-α，β-不饱和酮。通过使用该方法，从未改性的酮C-糖苷和醛中获得了一些复杂的（E）-α，β-不饱和酮C-糖苷。该反应通过新的途径进行，其中捕获并鉴定了特定的中间体。
• α,α-<i>bis</i>(BENZYLIDENE)CYCLOALKANONES BY CONDENSATION IN WATER UNDER PTC CATALYSIS AND MICROWAVE IRRADIATION
  作者：Jianfeng Zhou

  DOI：10.1080/00304940509355403

  日期：2005.2

  anones can be realized through cross aldol-type reaction of the ketones and aromatic aldehydes, but traditional acidor base-catalyzed reaction suffers from reverse reaction and thus gives the corresponding products in low yields.2 Aoyama and coworkers' obtained a,d-bis(benzy1idene)cyclohexanones through Rh(II1)-porphyrin complexcatalyzed condensation in only 30% yields, while Nakano and co-workers4

  双（对甲氧基苯基1）氧化碲在微波辐射下催化环烷酮和芳香醛的交叉羟醛缩合~n,~ FeCl,-6H20, SmCl, 在离子 KF-Al,O 中, 在超声辐射下,8 RuCl,,9 InCI,,,lO-'I 在文献中也有报道。报道了第一个在没有溶剂的情况下醛醇缩合的例子，有机化学家一直在寻求开发清洁、经济和环境更安全的方法。最近，人们越来越认识到水是许多有机反应的有吸引力的介质。由于反应清洁、快速且经济，因此将微波辐射用于有机反应已成为一种成熟的方法。在工业过程中应用相转移催化 (PTC) 代替传统技术为环境提供了巨大的好处。这些技术的组合一直是一个显示出极好的re~u1ts.l~作为我们兴趣的延续，我现在报告了a,a'-双（亚苄基）环烷酮的高效和清洁合成芳香醛与环戊酮和环己酮在碳酸钠水溶液中和在 Toda 等人的存在下缩合
• Gupta, Rajive; Gupta, Avinash K.; Paul, Satya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 1, p. 61 - 62
  作者：Gupta, Rajive、Gupta, Avinash K.、Paul, Satya、Kachroo, P. L.

  DOI：——

  日期：——
• Brahmbhatt; Pandya; Patel, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1863 - 1867
  作者：Brahmbhatt、Pandya、Patel、Patel

  DOI：——

  日期：——
• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.