1,4-di(2-furanyl)-1,4-butanedione | 22111-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di(2-furanyl)-1,4-butanedione
• 英文别名: (Difuryl-5',2'')-1,4 butanedione-1,4；1,4-di(furan-2-yl)butane-1,4-dione；1,4-difuran-2-ylbutane-1,4-dione；1,4-di(2-furyl)-1,4-butanedione；1,4-di(2-furyl)butane-1,4-dione；1,4-Di(2-furyl)-1,4-butandion；1,4-bis(furan-2-yl)butane-1,4-dione
• CAS: 22111-14-4
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: YFFKNPBNZUAMNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-di(2-furanyl)-1,4-butanedione 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以70%的产率得到2-[5-(呋喃-2-基)噻吩-2-基]呋喃
  参考文献：
  名称：

  Joshi, Makarand V.; Hemler, Christine; Cava, Michael P., Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1081 - 1086

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基呋喃 在 溴苯 、 silver fluoride 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.17h， 生成 1,4-di(2-furanyl)-1,4-butanedione
  参考文献：
  名称：

  硅基烯醇醚的银催化控制分子间交叉偶联：可扩展地获得 1,4-二酮

  摘要：

  公开了一种用于甲硅烷基烯醇化物的银催化受控分子间交叉偶联的方案。该协议显示出良好的官能团耐受性，并允许有效制备一系列合成有用的 1,4-二酮。初步的机理研究表明，该反应通过一个单电子过程进行，其中涉及自由基物质，其中 PhBr 充当氧化剂。

  DOI：

  10.1021/acs.orglett.2c01477

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。
• Novel fluorescent quater‐ and quinquifurans: Syntheses and photophysical properties
  作者：Joel M. Kauffman、Guillermo Moyna

  DOI：10.1002/jhet.5570390519

  日期：2002.9

  In the quest for fast fluors for use in waveshifting polystyrene fibers, symmetrical oligofurans were investigated. Furan moieties were coupled by means of the Ullmann Reaction or by palladium-catalyzed unsym-metrical coupling; the latter gave higher yields. While the benzoxazole-terminated quater- and quinquifurans we prepared were both stable and fast, exhibiting a green fluorescence and decay times

  为了寻求用于波移聚苯乙烯纤维的快速氟，对对称的低聚呋喃进行了研究。呋喃部分通过Ullmann反应或通过钯催化的非对称偶联而偶联。后者的产量更高。虽然我们制备的苯并恶唑封端的季铵盐和喹啉呋喃既稳定又快速，表现出绿色荧光，衰变时间约为2.4纳秒，但当掺入聚苯乙烯时，它们在溶解度和发射强度方面不如其他类型的荧光。
• Synthesis of 1,4-diketones by the coupling reaction of trimethylsilyl enol ethers with lead tetraacetate
  作者：Robert M. Moriarty、Raju Penmasta、Indra Prakash

  DOI：10.1016/s0040-4039(01)81011-x

  日期：1987.1

  Synthesis of 1,4-diketones in good yields was achieved by the coupling reaction of the trimethylsilyl enol ethers of acetophenone, thiophene or furan with lead tetraacetate in dry dichloromethane and tetrahydrofuran at −78°C.

  通过苯乙酮，噻吩或呋喃的三甲基甲硅烷基烯醇醚与四乙酸铅在干燥的二氯甲烷和四氢呋喃中于-78°C偶联反应，可实现高收率的1,4-二酮合成。
• Oxidative Coupling of Carbonyl Compounds by Using Pentavalent Biphenyl-2,2′-ylenebismuth Reagents
  作者：Shohei Imachi、Teruaki Mukaiyama

  DOI：10.1246/cl.2007.718

  日期：2007.6.5

  p-Tolylbiphenyl-2,2′-ylenebismuth bis(trifluoromethanesulfonate) reacted with lithium enolates derived from ketones, carboxylic esters, and thioesters to afford the corresponding oxidative coupling...

  p-Tolylbiphenyl-2,2'-ylenebismuth bis(trifluoromethanesulfonate) 与衍生自酮、羧酸酯和硫酯的烯醇锂反应，提供相应的氧化偶联...
• Process for the preparation of substituted indenes
  申请人：Hoechst Aktiengesellschaft

  公开号：US05194619A1

  公开（公告）日：1993-03-16

  The compounds of the formula I or Ia ##STR1## in which R.sup.1 is alkyl, aryl, alkoxy, alkenyl, arylalkyl, alkylaryl, aryloxy, fluoroalkyl, halogenoaryl, alkynyl, trialkylsilyl or a heteroaromatic radical, R.sup.2, R.sup.3 and R.sup.4, in addition to hydrogen, have the meanings given under R.sup.1 and R.sup.5 is hydrogen, alkyl, fluoroalkyl or alkenyl, can be obtained in a one-stage process by reaction of a compound II ##STR2## with (substituted) cyclopentadiene in the presence of a base. The compounds I and Ia are suitable as ligands for metallocene complexes which are used as catalysts in olefin polymerization.

  公式I或Ia的化合物##STR1##中，其中R.sup.1是烷基、芳基、烷氧基、烯基、芳基烷基、烷基芳基、芳氧基、氟烷基、卤代芳基、炔基、三烷基硅基或杂芳基，R.sup.2、R.sup.3和R.sup.4除了氢外，具有R.sup.1给定的含义，R.sup.5是氢、烷基、氟烷基或烯基，可以通过将化合物II##STR2##与（取代）环戊二烯在碱存在下反应而在一步过程中获得。化合物I和Ia适用作为配位基，用作烯烃聚合催化剂的茂金属配合物。