2-(3-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione | 136758-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(3-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione
• 英文别名: 2-{[3-(trifluoromethyl)phenyl]methylene}-1H-indene-1,3(2H)-dione；2-[[3-(trifluoromethyl)phenyl]methylidene]indene-1,3-dione
• CAS: 136758-25-3
• 化学式: C₁₇H₉F₃O₂
• 分子量: 302.252
• InChiKey: QXPKIPDYAIOYJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  433.2±45.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione 、 5-苯基-1,3,4-氧噻唑-2-酮 以 甲苯 为溶剂， 反应 18.0h， 以57%的产率得到3'-phenyl-5'-(3-(trifluoromethyl)phenyl)-5'H-spiro[indene-2,4'-isothiazole]-1,3-dione
  参考文献：
  名称：

  Synthesis of spiroindene-1,3-dione isothiazolines via a cascade michael/1,3-dipolar cycloaddition reaction of 1,3,4-oxathiazol-2-one and 2-arylidene-1,3-indandiones

  摘要：

  The reaction of 1,3,4-oxathiazol-2-one derivative with 2-arylidene-1,3-indandione to furnish novel spiroindene-1,3-dione isothiazoline derivatives by Michael/1,3-dipolar [3+2]-cycloaddition reaction was investigated. The key 1,3-dipolar cycloaddition reaction step was examined in toluene solvent at reflux temperature to obtain mixture of two regioisomers (6a and 6b - 14a and 14b) and single isomers (15-20). The scope of this new reaction was demonstrated with many examples with high reactivity and yields. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.12.089
• 作为产物：
  描述：

  1,3-茚满二酮 、 3-三氟甲基苯甲醛 在 L-脯氨酸 作用下， 以 甲醇 为溶剂， 以62.9 %的产率得到2-(3-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  作为选择性抗衣原体药物的二氢噻嗪类药物的设计、生物学评价和计算机辅助分析

  摘要：

  沙眼衣原体(CT) 导致美国最流行的性传播细菌性疾病。缺乏药物选择性是当前抗衣原体药物治疗的主要挑战之一。 CT 的代谢需求尤其受圆柱形蛋白酶及其分子伴侣（例如ClpX）的控制。研究表明，二氢硫氮卓类药物可以破坏 CT-ClpXP。基于此先例，我们合成了二氢硫氮杂卓文库，并使用改进的半高通量筛选测定法表征了其抗衣原体活性。然后，我们证明了它们在体外抑制 ClpX ATPase 活性的能力，支持 ClpX 作为靶点。此外，我们的先导化合物对 CT 表现出有前景的选择性、可接受的细胞毒性、无致突变潜力以及良好的体外稳定性。生成了二维定量结构-活性关系（2D QSAR）模型作为识别更有效的抗衣原体分子的支持工具。这项研究表明二氢噻嗪类药物是开发新型选择性抗衣原体药物的一个有希望的起点。

  DOI：

  10.1021/acs.jmedchem.2c01894

文献信息

• Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2-Arylidene-1,3-Indandiones: Synthesis of Tetrahydrofuran-Fused Spirocyclic 1,3-Indandiones
  作者：Huihui Zhang、Xing Gao、Feng Jiang、Wangyu Shi、Wei Wang、Yongjun Wu、Cheng Zhang、Xueyan Shi、Hongchao Guo

  DOI：10.1002/ejoc.202000762

  日期：2020.8.16

  An asymmetric [3+2] cycloaddition of 2‐arylidene‐1,3‐indandiones with vinylethylene carbonates in the presence of Pd2dba3· CHCl3 and axially chiral phosphoramidite ligand was developed.

  在Pd 2 dba 3 · CHCl 3和轴向手性亚磷酰胺配体存在下，开发了2-碳酸二亚乙烯酯-1,3-茚满二酮与碳酸亚乙烯酯的不对称[3 + 2]环加成反应。
• Construction of dispirocyclohexanes via amine-catalyzed [2 + 2 + 2] annulations of Morita–Baylis–Hillman acetates with exocyclic alkenes
  作者：Rongshun Chen、Silong Xu、Xia Fan、Hanyuan Li、Yuhai Tang、Zhengjie He

  DOI：10.1039/c4ob01927j

  日期：——

  Amine-catalyzed [2 + 2 + 2] annulations of one molecule of Morita–Baylis–Hillman (MBH) acetates 1 with two molecules of 2-(arylmethylidene)indane-1,3-diones 2 or methyleneindolinones 4 have been developed under very mild conditions, which produce multistereogenic dispirocyclohexanes 3 and 5, respectively, in moderate to excellent yields and good diastereoselectivity. This amine-catalyzed annulation constitutes

  胺催化的[2 + 2 + 2]森田-的Baylis-希尔曼（MBH）的一个分子乙酸盐annulations 1与2-（亚苄基）二氢化茚-1,3-二酮的两个分子2或methyleneindolinones 4已根据非常发达在中等至极好的收率和良好的非对映选择性下，温和的条件分别产生多立体异构的双螺环己烷3和5。这种胺催化的环化反应是构建双螺环己烷基序的一种新颖而有效的方法，并且就相应的膦催化的[3 + 2]环化反应而言，也展示了胺和膦之间的发散催化作用。
• Synthesis of dibenzo[<i>a</i>,<i>d</i>]cycloheptanoids <i>via</i> aryne insertion into 2-arylidene-1,3-indandiones
  作者：Nagaraju Payili、Santhosh Reddy Rekula、Anjaiah Aitha、V. V. S. R. N. Anji Karun Mutha、Challa Gangu Naidu、Satyanarayana Yennam

  DOI：10.1039/c9ob01900f

  日期：——

  A novel and unexpected aryne insertion cascade reaction on 2-arylidene-1,3-indandiones via conjugate addition of fluoride followed by formal C-C insertion is developed to afford dibenzo[a,d]cycloheptanoid derivatives in good yields with a single isomer. This reaction represents a rare instance of cyclic enone C-C bond insertion (acyl-alkenylation) in aryne chemistry. Interestingly, 2-arylidene-1,3-indandiones

  通过共轭添加氟化物，然后通过正式的CC插入，在2-芳基-1,3-茚满二酮上进行了新颖且出乎意料的芳烃插入级联反应，从而以单一异构体的高收率得到了二苯并[a，d]环庚烷衍生物。该反应代表了在芳烃化学中罕见的环状烯酮CC键插入（酰基-烯基化）的情况。有趣的是，带有富电子官能团的2-亚芳基-1,3-茚满二酮通过[4 + 2]环加成反应然后扩环提供二苯并[a，c]蒽-9,14-二酮衍生物。
• A convenient route to polyfunctionalised indeno[ 1,2 - b ]pyran derivatives
  作者：Jason Bloxham、Colin P. Dell

  DOI：10.1016/0040-4039(91)80626-h

  日期：1991.8

  2-Arylidene-1,3-indanediones undergo facile formal hetero-Diels-Alder cycloadditions with ynamines bearing electron-withdrawing groups yielding polyfunctionalised indeno[1,2-b]pyrans.
• Benzylidine indane-1,3-diones: As novel urease inhibitors; synthesis, in vitro, and in silico studies
  作者：Bilquees Bano、Kanwal、Khalid Mohammed Khan、Farida Begum、Muhammad Arif Lodhi、Uzma Salar、Ruqaiya Khalil、Zaheer Ul-Haq、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.09.030

  日期：2018.12

  Current study deals with the evaluation of indane-1,3-dione based compounds as new class of urease inhibitors. For that purpose, benzylidine indane-1,3-diones (1-30) were synthesized and fully characterized by different spectroscopic techniques including EI-MS, HREI-MS, H-1, and C-13 NMR. All synthetic molecules 1-30 were evaluated for urease inhibitory activity and showed good to moderate inhibitory potential within the range of (IC50 = 11.60 +/- 0.3-257.05 +/- 0.7 mu M) as compared to the standard acetohydroxamic acid (IC50 = 27.0 +/- 0.5 mu M). Compound 1 (IC50 = 11.60 +/- 0.3 mu M) was found to be most potent inhibitor amongst all derivatives. The key binding interactions of most active compounds within the enzyme pocket were evaluated through in silico studies.