1-(4-Methylphenyl)-4-(2-thienyl)-1,4-butandion | 77588-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Methylphenyl)-4-(2-thienyl)-1,4-butandion
• 英文别名: 1-(thiophen-2-yl)-4-(p-tolyl)butane-1,4-dione；1-(thiophen-2-yl)-4-p-tolylbutane-1,4-dione；1-(4-Methylphenyl)-4-(2-thienyl)-1,4-butanedione；1-(4-methylphenyl)-4-thiophen-2-ylbutane-1,4-dione
• CAS: 77588-53-5
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: HLQALWNJMWNTDB-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  433.7±30.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-Methylphenyl)-4-(2-thienyl)-1,4-butandion 在 对甲苯磺酸一水合物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2-[5-[1-(4-Methoxyphenyl)-5-(4-methylphenyl)pyrrol-2-yl]thiophen-2-yl]ethene-1,1,2-tricarbonitrile
  参考文献：
  名称：

  Formation of metal-lustrous organic crystals from 2-aryl-1-(4-methoxyphenyl)-5-(5-tricyanoethenyl-2-thienyl)pyrroles

  摘要：

  Various 2-aryl-1-(4-methoxyphenyl)-5-(5-tricyanoethenyl-2-thienyl)pyrroles (3) were synthesized. When the 2-aryl group of 3 is phenyl, 4-tolyt, and 4-methoxyphenyl, organic crystals with greenish yellow metallic luster are formed. In contrast, a 2-(4-fluorophenyl) derivative of 3 gives gold-like lustrous crystals. The relation of their crystal structures with the appearance of metallic color is mentioned. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.055
• 作为产物：
  描述：

  2-乙酰基噻吩 在 sodium hydride 、 potassium carbonate 、 乙酸乙酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 1-(4-Methylphenyl)-4-(2-thienyl)-1,4-butandion
  参考文献：
  名称：

  三氟甲基-β-二酮的三氟乙酰化反应：合成琥珀酰亚胺衍生物和1,4-二酮的简便方法

  摘要：

  已开发出三氟甲基-β-二酮的三氟乙酰化，可通过级联迈克尔加成反应/复古克莱森反应和亲核取代/复古克莱森反应合成琥珀酰亚胺和1,4-二酮。

  DOI：

  10.1002/ejoc.201800680

文献信息

• GAMMA-DIKETONES AS WNT/BETA -CATENIN SIGNALING PATHWAY ACTIVATORS
  申请人：Samumed, LLC

  公开号：US20140243349A1

  公开（公告）日：2014-08-28

  The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

  本公开提供了激活Wnt/β-连环蛋白信号通路并因此治疗或预防与信号转导相关的疾病的γ-二酮或其类似物；这些疾病包括骨质疏松症和骨关节病；骨发育不全、骨缺陷、骨折、牙周病、耳硬化症、伤口愈合、颅颌面缺陷、溶骨性骨病、创伤性脑损伤或脊柱损伤、与中枢神经系统分化和发育相关的脑萎缩/神经系统疾病，包括帕金森病、中风、缺血性脑疾病、癫痫、阿尔茨海默病、抑郁症、躁郁症、精神分裂症；耳部疾病如耳蜗毛细胞丧失；眼部疾病如老年性黄斑变性、糖尿病性黄斑水肿或视网膜色素变性以及与干细胞分化和生长相关的疾病，如脱发、造血相关疾病和组织再生相关疾病。
• Regioselective Annulation of Unsymmetrical 1,2-Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[<i>b</i>]thiophene Analogues
  作者：Ramakrishnan Sivasakthikumaran、Settu Muhammad Rafiq、Elumalai Sankar、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201501087

  日期：2015.12

  A systematic study on the regioselective cyclization of benzene- and naphthalene-based unsymmetrical diols with HBr (33 %) in acetic acid at room temperature led to the formation of annulation products. By using this method, synthesis of a wide variety of anthracene, tetracene and naphtho[b]thiophene analogues was achieved in good to excellent yields. By employing HBr (33 %) in acetic acid as a catalyst

  一项关于苯和萘基不对称二醇与 HBr (33%) 在室温下在乙酸中的区域选择性环化的系统研究导致形成环化产物。通过使用这种方法，合成了多种蒽、并四苯和萘并[b]噻吩类似物，收率良好至极好。通过在乙酸中使用 HBr (33 %) 作为不对称二醇区域选择性环化的催化剂，非常容易并且避免了常见的二氢异苯并呋喃形成。
• Synthesis of Water-Tolerant Indium Homoenolate in Aqueous Media and Its Application in the Synthesis of 1,4-Dicarbonyl Compounds via Palladium-Catalyzed Coupling with Acid Chloride
  作者：Zhi-Liang Shen、Kelvin Kau Kiat Goh、Hao-Lun Cheong、Colin Hong An Wong、Yin-Chang Lai、Yong-Sheng Yang、Teck-Peng Loh

  DOI：10.1021/ja106925f

  日期：2010.11.17

  The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl(3) to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl(2) was used in place of In/InCl(3). The synthetic utility of the indium homoenolate

  第一个耐水、酮型的均烯化铟是通过将 In/InCl(3) 氧化添加到烯酮合成的。该反应仅在水性介质中进行。铟和氯化铟 (III) 都是反应顺利转化所必需的。当使用 InCl 或 InCl(2) 代替 In/InCl(3) 时，获得了类似的结果。通过钯催化的均烯酸铟与酰氯的偶联合成 1,4-二羰基化合物，证明了均烯酸铟的合成效用。
• Electrochemical chemoselective hydrogenation of 1,4-enediones with HFIP as the hydrogen donor: scalable access to 1,4-diketones
  作者：Hao-Ran Li、Xue-Yang Guo、Ming-Zhong Guo、Kui Liu、Li-Rong Wen、Ming Li、Lin-Bao Zhang

  DOI：10.1039/d3ob01465g

  日期：——

  versatile 1,4-diketones are smoothly generated under metal-free and external-reductant-free electrolytic conditions. Moreover, the tolerance of various functional groups and decagram-scale experiments have shown the practicability and potential applications of this methodology. Moreover, a range of heterocyclic compounds were easily prepared through follow-up procedures of 1,4-diketones.

  已经报道了在未分割的电池中有效氢化不饱和 C C 键的简单电化学方案。在无金属和无外部还原剂的电解条件下顺利生成一系列多功能的1,4-二酮。此外，各种官能团的耐受性和十克规模的实验表明了该方法的实用性和潜在应用。此外，通过1,4-二酮的后续程序可以轻松制备一系列杂环化合物。
• Photoredox-catalyzed 1,2-oxo-alkylation of vinyl arenes with 1,3-diketones: an approach to 1,4-dicarbonyls <i>via</i> C–C activation
  作者：Pushbaraj Palani、Ajithkumar Arumugam、Dineshkumar Raja、Kesavan Muthu、Gopal Chandru Senadi

  DOI：10.1039/d3cc02366d

  日期：——

  A mild approach to 1,4-diketones in moderate to excellent yields via 1,2-oxo alkylation has been developed using visible-light photocatalysis. The notable feature is the late-stage functionalization of thymol and ibuprofen derivatives.

  我们利用可见光光催化技术开发出了一种温和的方法，通过 1,2-oxo 烷基化反应以中等至极好的收率获得 1,4-二酮。其显著特点是百里酚和布洛芬衍生物的后期官能化。