2,6-bis(2-bromobenzylidene)cyclohexanone

• 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(2-bromobenzylidene)cyclohexanone
• 英文别名: 2,6-Bis[(2-bromophenyl)methylidene]cyclohexan-1-one；2,6-bis[(2-bromophenyl)methylidene]cyclohexan-1-one
• 化学式: C₂₀H₁₆Br₂O
• mdl: MFCD08560109
• 分子量: 432.154
• InChiKey: IYUMKWYJTLIPIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 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：

  二聚氰胺 、 2,6-bis(2-bromobenzylidene)cyclohexanone 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以79%的产率得到8-(2-bromobenzylidene)-4-(2-bromophenyl)-2-cyanoimino-1,2,3,4,5,6,7,8-octahydroquinazoline
  参考文献：
  名称：

  A methodological approach for the synthesis of 4-aryl-8-arylidene-2-cyanoimino-1,2,3,4,5,6,7,8-octahydroquinazolines

  摘要：

  Abstract An efficient methodological approach for the synthesis of a novel series of 4-aryl-8-arylidene-2-cyanoimino-1,2,3,4,5,6,7,8-octahydroquinazolines (aryl-CIOHQs) was presented via one-pot four-component reaction of cyclohexanone, two-folds of various aromatic aldehydes and cyanoguanidine in the presence of sodium ethoxide as basic catalyst. The same target products (aryl-CIOHQs) were also reproduced

  DOI：

  10.1080/00397911.2022.2072747
• 作为产物：
  描述：

  环己酮 、 邻溴苯甲醛 在 [Cp₂-Ti(η¹-salicylato)(η¹-4-fluorobenzoato)] 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以94%的产率得到2,6-bis(2-bromobenzylidene)cyclohexanone
  参考文献：
  名称：

  空气稳定的混合双羧酸二茂钛配合物的合成及其在交叉羟醛和曼尼希反应中的催化行为

  摘要：

  摘要 以水杨酸 (H2-Sal) 与苯甲酸 (H-Ben)、4-氟苯甲酸 (H-BenF) 和 3-噻吩酸 (H-Th) 作为混合配体，开发了可调有机金属路易斯酸催化剂。双羧酸二茂钛络合物。三种空气稳定配合物 [Cp2Ti(η1-HSal)(η1-Ben)] (1), [Cp2Ti(η1-HSal)(η1-BenF)] (2) 和 [Cp2Ti[η1-HSal][(η1- Th)] (3) 通过水杨酸二茂钛螯合物与羧酸盐配体的反应以高产率制备。通过物理化学和光谱方法充分表征了混合的双羧酸二茂钛配合物。单晶 X 射线衍射研究揭示了 Ti-O(H-Sal) 键距分别为 1.972(3)、1.9245(18) 和 1.912(5) Å，而键距涉及1、2 和 3 的配体为 1.908(3) Å (Ti-OBen)、1.9296(19) Å (Ti-OBenF) 和 1。分别为 945(5) Å (

  DOI：

  10.1007/s11243-016-0054-3

文献信息

• Synthesis and Fluorescence Properties of α,α′-Bis(substituted-benzylidene)cycloalkanones Catalyzed by 1-Methyl-3(2-(sulfooxy)ethyl)-1<i>H</i>-imidazol-3-ium Chloride
  作者：Yu Wan、Xiu-Mei Chen、Li-Ling Pang、Rui Ma、Cai-Hui Yue、Rui Yuan、Wei Lin、Wei Yin、Rong-Cheng Bo、Hui Wu

  DOI：10.1080/00397910903243781

  日期：2010.7.12

  α,α′-Bis(substituted-benzylidene)cycloalkanones were synthesized via a solvent-free cross-aldol condensation of aromatic aldehydes with cycloalkanones in the presence of a catalytic amount 1-methyl-3(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride at room temperature with excellent yields. The screening for optical properties indicated that the size of cycloalkanone has an influence on the fluorescence

  在催化量的 1-甲基-3(2-(磺氧基)乙基)-1H 存在下，通过芳香醛与环烷酮的无溶剂交叉羟醛缩合反应合成了 α,α'-双（取代亚苄基）环烷酮-咪唑-3-氯化鎓在室温下以优异的收率。光学性质的筛选表明，环烷酮的大小对产物的荧光发射有影响。来自环己酮的产物比来自环戊酮的产物具有更强的荧光发射。
• Synthesis of air-stable mixed bis-carboxylate titanocene complexes and their catalytic behaviors in cross-aldol and Mannich reactions
  作者：Jing Wang、Xi Chen、Xiu Wang、Wei-Qiang Zhang、Hua-Ming Sun、Guo-Fang Zhang、Ya Wu、Zi-Wei Gao

  DOI：10.1007/s11243-016-0054-3

  日期：2016.10

  Abstract Tunable organometallic Lewis acid catalysts were developed by combining salicylic acid (H2-Sal) with benzoic acid (H-Ben), 4-fluorobenzoic acid (H-BenF) and 3-thiophenic acid (H-Th), as coligands for mixed bis-carboxylate titanocene complexes. Three air-stable complexes [Cp2Ti(η1-HSal)(η1-Ben)] (1), [Cp2Ti(η1-HSal)(η1-BenF)] (2) and [Cp2Ti[η1-HSal][(η1-Th)] (3) were prepared in high yields

  摘要 以水杨酸 (H2-Sal) 与苯甲酸 (H-Ben)、4-氟苯甲酸 (H-BenF) 和 3-噻吩酸 (H-Th) 作为混合配体，开发了可调有机金属路易斯酸催化剂。双羧酸二茂钛络合物。三种空气稳定配合物 [Cp2Ti(η1-HSal)(η1-Ben)] (1), [Cp2Ti(η1-HSal)(η1-BenF)] (2) 和 [Cp2Ti[η1-HSal][(η1- Th)] (3) 通过水杨酸二茂钛螯合物与羧酸盐配体的反应以高产率制备。通过物理化学和光谱方法充分表征了混合的双羧酸二茂钛配合物。单晶 X 射线衍射研究揭示了 Ti-O(H-Sal) 键距分别为 1.972(3)、1.9245(18) 和 1.912(5) Å，而键距涉及1、2 和 3 的配体为 1.908(3) Å (Ti-OBen)、1.9296(19) Å (Ti-OBenF) 和 1。分别为 945(5) Å (
• A RhCl(PPh3)3/BF3·OEt2 co-promoted direct C–C cross-coupling of alcohols at β-position with aldehydes
  作者：Shu-Yu Zhang、Yong-Qiang Tu、Chun-An Fan、Ming Yang、Fu-Min Zhang

  DOI：10.1016/j.tetlet.2009.05.006

  日期：2009.7

  A novel RhCl(PPh3)(3)/BF3 center dot OEt2 co-promoted direct C-C cross-coupling of primary and secondary alcohols at beta-position with aldehyde was developed. This reaction could provide an efficient synthesis of a series of alpha, beta-unsaturated aldehydes and diarylidene ketones, just from simple and easily available alcohols and aldehydes. (C) 2009 Elsevier Ltd. All rights reserved.
• Hu, Xueyuan; Fan, Xuesen; Zhang, Xinying, Journal of Chemical Research, 2004, # 10, p. 684 - 686
  作者：Hu, Xueyuan、Fan, Xuesen、Zhang, Xinying、Wang, Jianji

  DOI：——

  日期：——
• In-Vitro and In-Silico Evaluations of Heterocyclic-Containing Diarylpentanoids as Bcl-2 Inhibitors Against LoVo Colorectal Cancer Cells
  作者：Sze Wei Leong、Suet Lin Chia、Faridah Abas、Khatijah Yusoff

  DOI：10.3390/molecules25173877

  日期：——

  In the present study, we investigated the in-vitro anti-cancer potential of six diarylpentanoids against a panel of BRAF- and KRAS-mutated colorectal cancer cell lines including T84, SW620, LoVo, HT29, NCI-H508, RKO, and LS411N cells. Structure–activity relationship study suggested that the insertions of tetrahydro-4H-thiopyran-4-one and brominated phenyl moieties are essential for better cytotoxicity. Among the evaluated analogs, 2e has been identified as the lead compound due to its low IC50 values of approximately 1 µM across all cancer cell lines and high chemotherapeutic index of 7.1. Anti-proliferative studies on LoVo cells showed that 2e could inhibit cell proliferation and colony formations by inducing G2/M cell cycle arrest. Subsequent cell apoptosis assay confirmed that 2e is a Bcl-2 inhibitor that could induce intrinsic cell apoptosis by creating a cellular redox imbalance through its direct inhibition on the Bcl-2 protein. Further molecular docking studies revealed that the bromophenyl moieties of 2e could interact with the Bcl-2 surface pocket through hydrophobic interaction, while the tetrahydro-4H-thiopyran-4-one fragment could form additional Pi-sulfur and Pi-alkyl interactions in the same binding site. In all, the present results suggest that 2e could be a potent lead that deserves further modification and investigation in the development of a new Bcl-2 inhibitor.

  在本研究中，我们研究了六种二苯基戊酮类化合物对一系列BRAF和KRAS突变结肠癌细胞系（包括T84、SW620、LoVo、HT29、NCI-H508、RKO和LS411N细胞）的体外抗癌潜力。结构-活性关系研究表明，四氢-4H-噻吩-4-酮和溴苯基团的插入对更好的细胞毒性至关重要。在评估的类似物中，2e被确定为主导化合物，因为它在所有癌细胞系中的低IC50值约为1微米，且具有7.1的高化疗指数。对LoVo细胞的抗增殖研究表明，2e能通过诱导G2/M细胞周期阻滞来抑制细胞增殖和集落形成。随后的细胞凋亡实验证实，2e是一种Bcl-2抑制剂，可以通过直接抑制Bcl-2蛋白而引起内在细胞凋亡，从而产生细胞氧化还原不平衡。进一步的分子对接研究揭示，2e的溴苯基团可以通过疏水相互作用与Bcl-2表面口袋发生相互作用，而四氢-4H-噻吩-4-酮片段可以在同一结合位点形成额外的Pi-硫和Pi-烷基相互作用。总的来说，目前的结果表明，2e可能是一个值得进一步修饰和研究的有效主导化合物，用于开发新的Bcl-2抑制剂。