2,6-bis((E)-2,6-dichlorobenzylidene)cyclohexan-1-one | 42426-37-9

• 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((E)-2,6-dichlorobenzylidene)cyclohexan-1-one
• 英文别名: (2E,6E)-2,6-bis(2,6-dichlorobenzylidene)cyclohexanone；(2E,6E)-2,6-bis[(2,6-dichlorophenyl)methylidene]cyclohexan-1-one
• CAS: 42426-37-9
• 化学式: C₂₀H₁₄Cl₄O
• 分子量: 412.143
• InChiKey: QGRADUQJYBJJER-DCIPZJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  25
• 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：

  氨基硫脲 、 2,6-bis((E)-2,6-dichlorobenzylidene)cyclohexan-1-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以70.6%的产率得到(E)-7-(2,6-dichlorobenzylidene)-3-(2,6-dichlorophenyl)-3,3a,4,5,6,7-hexahydro-2Hindazole-2-carbothioamide
  参考文献：
  名称：

  双查尔酮衍生的新型稠合吡唑啉衍生物抗乳腺癌细胞的合成、表征、细胞毒性研究和对接研究

  摘要：

  DOI：

  10.21608/ejchem.2021.73796.3648
• 作为产物：
  描述：

  环己酮 、 2,6-二氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以96%的产率得到2,6-bis((E)-2,6-dichlorobenzylidene)cyclohexan-1-one
  参考文献：
  名称：

  基于环己酮支架的查耳酮的合成和 X 射线晶体结构结合构象和 Hirshfeld 分析

  摘要：

  摘要 提出了四种基于环己酮核的查耳酮结构。使用分光光度法和单晶 X 射线技术阐明了双亚苄基环己酮类似物 3a-d 的结构。化合物3a、3b和3d在单斜晶系中结晶，空间群为P21/c。然而，3c 在空间群为 Pna21 的正交晶系中结晶。进行了一系列与结构相关的计算研究。使用 B3LYP 方法和 6-31G(d,p) 基组，对所研究的二烯酮的分子结构进行了优化，然后评估了它们的电子特性和紫外-可见光谱。键距和角度与实验数据相关。所有的二烯酮都通过 C–H⋯O 分子内氢键相互作用稳定。在 3c 中每个苯环的邻位存在两个 Cl 原子导致与环己酮环的空间位阻，导致所研究化合物中最弱的 H⋯O 相互作用。TD-DFT 方法用于分配和解释所研究的二烯酮的电子光谱的起源。

  DOI：

  10.1016/j.molstruc.2019.126873

文献信息

• Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines
  作者：Mengna Zhi、Zhenjie Gan、Rong Ma、Hao Cui、Er-Qing Li、Zheng Duan、François Mathey

  DOI：10.1021/acs.orglett.9b00926

  日期：2019.5.3

  A Ag/P-stereogenic phosphine-complex-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with electron-deficient olefins is reported. In this reaction, highly functionalized pyrrolines with a spiro-quaternary stereogenic center were obtained in good yields (up to 99%) with excellent levels of diastereo- (up to >20:1 dr) and enantioselectivities (up to >99% ee). The chirality of adducts was controlled

  报道了Ag / P-立体异构的膦复合物催化的偶氮甲亚胺的1,3-偶极环加成与缺电子的烯烃。在该反应中，获得了具有螺四元立体构型中心的高度官能化的吡咯啉，收率好（高达99％），非对映体（高达> 20：1 dr）和对映体选择性（高达> 99％ee） 。加合物的手性主要受P-立体生成的膦所控制。
• Symmetrical and unsymmetrical substituted 2,5-diarylidene cyclohexanones as anti-parasitic compounds
  作者：Zia Ud Din、Marilia Almeida Trapp、Lívia Soman de Medeiros、Danielle Lazarin-Bidóia、Francielle Pelegrin Garcia、Francieli Peron、Celso Vataru Nakamura、Ihosvany Camps Rodríguez、Abdul Wadood、Edson Rodrigues-Filho

  DOI：10.1016/j.ejmech.2018.06.031

  日期：2018.7

  epimastigoteand trypomastigoteof Trypanosoma cruzi. Eighteen compounds displayed anti-leishmanial activity against promastigotes of L. amazonensis with IC50 values ranging from 2.8 to 10 μM. In addition, two compounds exhibited significant antitrypanosomal activity against epimastigotes of T. cruzi with IC50 values of 5.2 ± 0.8 and 3.0 ± 0.0 μM, while five compounds exhibited activity from 15.0 ± 1.4 to 30.2 ± 1

  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
• Mass Spectrometry of Some Substituted 2-Benzylidenecyclohexanones and 2,6-bis-Benzylidenecyclohexanones
  作者：P. J. Smith、J. R. Dimmock、W. A. Turner

  DOI：10.1139/v73-220

  日期：1973.5.1

  The mass spectra of a series of some substituted 2-benzylidenecyclohexanones and a series of substituted 2,6-bis-benzylidenecyclohexanones have been determined at 70 eV. The major fragmentation pathways include an intramolecular aromatic substitution reaction leading to the loss of an ortho-substituent with the formation of a stable benzopyrylium ion, loss of carbon monoxide and ethylene from the parent ion and also further ions derived from subsequent cleavages of the cyclohexanone ring. The structural and electronic factors involved in the aromatic substitution reaction were examined by comparing the M – H/M and M – Cl/M ratios determined from the spectra of the various substrates.

  已确定了一系列一些取代的2-苄基亚甲基环己酮和一系列取代的2,6-双苄亚甲基环己酮的质谱在70 eV下。主要的碎裂途径包括分子内芳香取代反应，导致邻位取代基的丢失，形成稳定的苯并吡啶离子，从母离子中丢失一氧化碳和乙烯，以及从环己酮环的后续断裂中派生出的更多离子。通过比较从各种底物的光谱中确定的M - H/M和M - Cl/M比率，研究了参与芳香取代反应的结构和电子因素。
• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：——

  公开号：US20020040029A1

  公开（公告）日：2002-04-04

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, including angiongenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及香豆素和香豆素衍生物以及类似物，这些化合物可用作抗血管生成抑制剂。这些化合物的合成成本低廉，并表现出出乎意料的良好的抗血管生成活性。本发明还涉及使用香豆素及其类似物作为抗肿瘤/抗癌剂，以及治疗一些与血管生成有关的疾病或病态，包括血管生成性皮肤病如牛皮癣、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等等，以及慢性炎症性疾病如关节炎。
• Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
  作者：Lorraine M. Deck、Lucy A. Hunsaker、Thomas A. Vander Jagt、Lisa J. Whalen、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.ejmech.2017.11.048

  日期：2018.1

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.