1,4-bis(5-methyl-2-thienyl)-1,4-butanedione | 212116-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis(5-methyl-2-thienyl)-1,4-butanedione
• 英文别名: 1,4-Bis(5-methyl-2-thienyl)butane-1,4-dione；1,4-bis(5-methylthiophen-2-yl)butane-1,4-dione
• CAS: 212116-54-6
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: XDHUPEAFWOQHNU-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  456.5±45.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(5-methyl-2-thienyl)-1,4-butanedione 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2,5-bis(5-methyl-2-furyl)thiophene
  参考文献：
  名称：

  α-Linked Bifuran and α,α‘-Linked Tricycles Containing Furan and/or Thiophene. EPR Investigations and Electrochemical Behavior

  摘要：

  The radical cations from 5,5'-dimethyl-2,2'-bifuran (1) and 5,5 "-dimethyl-2,2',5',2 "-terfuran (5), and from the alpha,alpha'-linked triheterocycles containing thiophene and furan, bis(5-methyl-2-furyl)thiophene (6) and bis(5-methyl-2-thienyl)furan (7), were generated in fluid solution with trifluoroacetic acid (TFA) or mixtures of TFA and 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP), in the presence or absence of thallium(III) trifluoroacetate as oxidant, and analyzed by electron paramagnetic resonance. The hyperfine coupling (hc) constants were assigned by comparison with those from 5,5'-dimethyl- (3) and 5,5'-di-tert-butyl-2,2',5',2 "-terthiophene (4) and by investigation into the deuterated species generated in solution with deuteriotrifluoroacetic acid and, in the case of 5(.+), 6(.+), and 7(.+) confirmed by theoretical calculations. The parent compounds 1, 5, 6, and 7 were synthesized by known procedures. Cyclic voltammetry of them in dimethylformamide using tetrabutylammonium hexafluorophosphate or perchlorate as electrolyte display irreversible oxidation peaks. The anodic peak for the oxidation of terfuran 5 is lower than that of bifuran 1, and anodic peaks for the oxidation of the trimers with furan rings 6 and 7 are lower than those for terthiophenes 3 and 4.

  DOI：

  10.1021/jo9719618
• 作为产物：
  描述：

  2-甲基噻吩 、 丁二酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 以10%的产率得到1,4-bis(5-methyl-2-thienyl)-1,4-butanedione
  参考文献：
  名称：

  丁二氯与噻吩在Friedel-Crafts反应中的行为特点*

  摘要：

  在AlCl 3，TiCl 4和SnCl 4的存在下，研究了噻吩，2-甲基和2-溴噻吩与琥珀酰二氯的反应。酰化条件，路易斯酸的相对数量和性质对1,4-二（2-噻吩基）-1,4-二酮和4-氧代-4-（2-噻吩基）的比率和收率的影响已证明形成了丁酸。在反应条件下，证明了4,4-二（2-噻吩基）丁-3-烯酸（在许多情况下是主要产物）的形成以及4,4-二（2-噻吩基）-丁内酯的形成。

  DOI：

  10.1007/s10593-011-0653-z

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。
• Incorporation of Stable Organic Radicals of the Tris(2,4,6-trichlorophenyl)methyl Radical Series to Pyrrole Units as Models for Semiconducting Polymers with High Spin Multiplicity. 1. [2,6-Dichloro-4-[2,5-bis(5-methyl-2-thienyl)- 1-pyrrolyl]phenyl]bis(2,4,6-trichlorophenyl)methyl Radical as a Precursor of a Disjoint Heterospin Diradical with a Triplet or a Nearly Degenerate Singlet−Triplet Ground State
  作者：V. M. Domingo、X. Burdons、E. Brillas、J. Carilla、J. Rius、X. Torrelles、L. Juliá

  DOI：10.1021/jo000217b

  日期：2000.10.1

  6-dichlorophenyl)bis(2, 4,6-trichlorophenyl)methyl radical and acetylacetone or 1, 4-bis(5-methyl-2-thienyl)-1,4-butanedione yield [2,6-dichloro-4-(2, 5-dimethyl-1-pyrrolyl)phenyl]bis(2,4,6-trichlorophenyl)methyl radical (3(*)()) and [2,6-dichloro-4-[2, 5-bis(5-methyl-2-thienyl)-1-pyrrolyl]phenyl]bis(2,4, 6-trichlorophenyl)methyl radical (4(*)()), respectively. EPR studies of both radicals 3(*)() and 4(*)() in CH(2)Cl(2)

  （4-氨基-2,6-二氯苯基）双（2,4,6-三氯苯基）甲基与乙酰丙酮或1,4-双（5-甲基-2-噻吩基）-1,4-丁二酮之间的缩合反应产生[2,6-二氯-4-（2,5-二甲基-1-吡咯基）苯基]双（2,4,6-三氯苯基）甲基（3（*）（））和[2,6-二氯-4- [2,5-双（5-甲基-2-噻吩基）-1-吡咯基]苯基]双（2,4,6-三氯苯基）甲基（4（*）（））。对CH（2）Cl（2）解决方案中的自由基3（*）（）和4（*）（）的EPR研究表明，弱电子离域作用与六个芳族氢的偶合常数分别为1.25和1.30 G 。通过循环伏安法分析了它们的电化学行为。相对于SSCE，两个自由基均显示出在E度分别为-0.69 V和-0.61 V时可逆的还原过程，在E（p）（a）= 1.10和0.72 V时的阳极峰值电位，相对于SSCE在200 mV s（-）（1）的扫描速率下（nu）是可逆的。自由基3（*）（）的X射线分析表明，在2
• Peculiarities of the behavior of succinyl dichloride in Friedel-Crafts reaction with thiophenes*
  作者：V. I. Smirnov、A. V. Afanas’ev、L. I. Belen’kii

  DOI：10.1007/s10593-011-0653-z

  日期：2011.1

  The reactions of thiophene, 2-methyl-, and 2-bromothiophene with succinyl dichloride in the presence of AlCl3, TiCl4, and SnCl4 have been studied. The effect of the acylation conditions, the relative amounts and nature of the Lewis acid on the ratio and yields of the 1,4-di(2-thienyl)-1,4-diones and 4-oxo-4-(2-thienyl)butyric acids formed have been demonstrated. Under the reaction conditions, the formation

  在AlCl 3，TiCl 4和SnCl 4的存在下，研究了噻吩，2-甲基和2-溴噻吩与琥珀酰二氯的反应。酰化条件，路易斯酸的相对数量和性质对1,4-二（2-噻吩基）-1,4-二酮和4-氧代-4-（2-噻吩基）的比率和收率的影响已证明形成了丁酸。在反应条件下，证明了4,4-二（2-噻吩基）丁-3-烯酸（在许多情况下是主要产物）的形成以及4,4-二（2-噻吩基）-丁内酯的形成。
• Gamma-diketones for treatment and prevention of aging skin and wrinkles
  申请人：Samumed, LLC

  公开号：US10434052B2

  公开（公告）日：2019-10-08

  The present disclosure relates to compounds having the following structure: or a dermatologically acceptable salt thereof, and cosmetic or dermopharmaceutical compositions comprising the same, and methods for using the compounds or compositions for treating, protecting, and/or improving the condition and/or aesthetic appearance of skin, for example, treating, preventing, ameliorating, reducing and/or eliminating fine lines and/or wrinkles of skin, or improving the appearance of fine lines and/or or wrinkles of skin comprising application of the compounds or compositions disclosed.

  本公开涉及具有以下结构的化合物： 或其皮肤学上可接受的盐，以及包含这些化合物的化妆品或皮肤药物组合物，以及使用这些化合物或组合物治疗、保护和/或改善皮肤状况和/或美学外观的方法，例如，治疗、预防、改善、减少和/或消除皮肤细纹和/或皱纹，或改善皮肤细纹和/或或皱纹的外观，包括应用所公开的化合物或组合物。
• γ-diketones as Wnt/β-catenin signaling pathway activators
  申请人：Samumed, LLC

  公开号：US10457672B2

  公开（公告）日：2019-10-29

  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γ-二酮或其类似物，它们能激活Wnt/β-catenin信号转导，从而治疗或预防与信号转导有关的疾病，如骨质疏松症和骨关节病；成骨不全症、骨缺损、骨折、牙周病、耳硬化症、伤口愈合、颅面缺损、溶瘤性骨病、脑外伤或脊柱损伤、脑萎缩/与中枢神经系统分化和发育有关的神经系统疾病，包括帕金森病、中风、缺血性脑病、癫痫、阿尔茨海默病、抑郁症、躁狂症、精神分裂症；耳部疾病，如耳蜗毛细胞缺失；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有关的疾病，如脱发、造血相关疾病和组织再生相关疾病。