5,6-双(溴甲基)-1,3-苯并二氧杂环戊烯 | 114394-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 5,6-双(溴甲基)-1,3-苯并二氧杂环戊烯
• 英文名称: 1,2-methylenedioxy-4,5-dibromomethylbenzene
• 英文别名: 5,6-bis(bromomethyl)-1,3-benzodioxole；5,6-bis-bromomethyl-benzo[1,3]dioxole；5,6-Bis(bromomethyl)benzo[d][1,3]dioxole
• CAS: 114394-68-2
• 化学式: C₉H₈Br₂O₂
• 分子量: 307.969
• InChiKey: NXXCPCONRWLAAE-UHFFFAOYSA-N

物化性质

• 熔点：
  112.4-114.2 °C(Solv: hexane (110-54-3); toluene (108-88-3))
• 沸点：
  343.3±37.0 °C(Predicted)
• 密度：
  1.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-双(溴甲基)-1,3-苯并二氧杂环戊烯 在 palladium on activated charcoal aluminum tri-bromide 、 氢气 、 乙醇锂 、 乙硫醇 作用下， 以 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.0h， 生成 4,5-dioctyl-1,2-dihydroxybenzene
  参考文献：
  名称：

  TOWARD BORONATE ESTER MESOGENIC STRUCTURES

  摘要：

  This article describes efforts toward the development of a new core for calamitic mesogens based upon the introduction of an extended heteroaromatic boron-containing ring. A series of tri-catenar mesogenic boronate ester derivatives of the 2-phenyl-1,3,2-benzodioxaborole has been synthesized and characterized. The flat central core appeared to be a suitable feature for these derivatives to support anisotropic alignment. Additionally, these derivatives should possess an inherent dipole in the core. However, thermal analysis (polarized optical microscopy and differential scanning calorimetry) did not reveal any mesophases.

  DOI：

  10.1080/15421400390223158
• 作为产物：
  描述：

  胡椒环 、 聚合甲醛 在 氢溴酸 、 溶剂黄146 作用下， 以71%的产率得到5,6-双(溴甲基)-1,3-苯并二氧杂环戊烯
  参考文献：
  名称：

  TOWARD BORONATE ESTER MESOGENIC STRUCTURES

  摘要：

  This article describes efforts toward the development of a new core for calamitic mesogens based upon the introduction of an extended heteroaromatic boron-containing ring. A series of tri-catenar mesogenic boronate ester derivatives of the 2-phenyl-1,3,2-benzodioxaborole has been synthesized and characterized. The flat central core appeared to be a suitable feature for these derivatives to support anisotropic alignment. Additionally, these derivatives should possess an inherent dipole in the core. However, thermal analysis (polarized optical microscopy and differential scanning calorimetry) did not reveal any mesophases.

  DOI：

  10.1080/15421400390223158

文献信息

• A One-Pot Cascade to Protoberberine Alkaloids via Stevens Rearrangement of Nitrile-Stabilized Ammonium Ylides
  作者：Günther Lahm、Jan-Gernot Deichmann、Anna Lisa Rauen、Till Opatz

  DOI：10.1021/jo502842s

  日期：2015.2.6

  A facile one-pot synthesis of protoberberines from readily accessible 1,2,3,4-tetrahydroisoquinoline-1-carbonitriles and 1,2-bis(bromomethyl)arenes is described. The reaction cascade comprises four consecutive transformations, all of which can be effected under a single set of conditions. Ten protoberberines, including the alkaloids pseudopalmatine and pseudoepiberberine, were prepared in yields up

  描述了从容易获得的1,2,3,4-四氢异喹啉-1-腈和1,2-双（溴甲基）芳烃轻松合成一锅小ber碱的方法。反应级联反应包括四个连续的转化，所有这些转化都可以在一组条件下进行。根据该策略，制备了十种原小ber碱，包括生物碱类伪帕金汀和伪小iber碱，收率高达86％。不需要色谱纯化产物，并且该路线没有任何保护基操纵。
• Synthesis and antimicrobial activity of chiral quaternary <em>N</em>-spiro ammonium bromides with 3',4'-dihydro-1'H-spiro[isoindoline-2,2'-isoquinoline] skeleton
  作者：Krzysztof Bielawski、Katarzyna Leszczyńska、Zbigniew Kałuża、Anna Bielawska、Olga Michalak、Tamara Daniluk、Olga Staszewska-Krajewska、Anna Czajkowska、Natalia Pawłowska、Agnieszka Gornowicz

  DOI：10.2147/dddt.s133250

  日期：——

  strongest antibacterial properties toward some gram-negative bacteria (M. catarrhalis and C. jejuni) with a high level of selectivity. High antibacterial compounds have bactericidal activity ratio MBC/MIC ≤4. Our studies also proved that the novel compounds do not possess cytotoxic and proapoptotic potential in normal cells.

  从一个容易获得的L-酒石酸开始合成了一类具有季碳立体中心的新型高度官能化的四氢异喹啉。使用9种细菌菌株（金黄色葡萄球菌，化脓性链球菌，变形链球菌，唾液链球菌，枯草芽孢杆菌，粪肠球菌，卡他莫拉氏菌，大肠埃希氏菌，空肠弯曲菌）测定最小抑菌浓度（MB） ）合成的化合物。确定了分析的化合物对人皮肤成纤维细胞活力和凋亡诱导的影响。大多数合成的化合物对某些革兰氏阴性细菌（卡他莫拉氏菌和空肠弯曲杆菌）表现出最强的抗菌性能，并且具有很高的选择性。高抗菌化合物的杀菌活性比MBC / MIC≤4。我们的研究还证明，该新型化合物在正常细胞中不具有细胞毒性和促凋亡潜力。
• HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：Reddy Panduranga Adulla P.

  公开号：US20100286135A1

  公开（公告）日：2010-11-11

  The present invention relates to novel heterocyclic amide compounds of Formula I: as disclosed herein or a pharmaceutically acceptable salt, solvate, ester, prodrug or stereoisomer thereof. Also disclosed are compositions comprising said compounds, and methods for using said compounds for treating or preventing a proliferative disease, an anti-proliferative disorder, inflammation, arthritis, a neurological or neurodegenerative disease, a cardiovascular disease, alopecia, a neuronal disease, an ischemic injury, a viral disease or a fungal disease.

  本发明涉及公式I的新异环酰胺化合物，如本文所述或其药学上可接受的盐、溶剂化物、酯、前药或立体异构体。还公开了包含该化合物的组合物，并且公开了使用该化合物治疗或预防增殖性疾病、抗增殖性障碍、炎症、关节炎、神经或神经退行性疾病、心血管疾病、脱发、神经元疾病、缺血性损伤、病毒性疾病或真菌病的方法。
• [EN] HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES D'AMIDE EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：SCHERING CORP

  公开号：WO2009014637A3

  公开（公告）日：2009-03-19
• Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives
  作者：Angela Schöffmann、Laurin Wimmer、Daria Goldmann、Sophia Khom、Juliane Hintersteiner、Igor Baburin、Thomas Schwarz、Michael Hintersteininger、Peter Pakfeifer、Mouhssin Oufir、Matthias Hamburger、Thomas Erker、Gerhard F. Ecker、Marko D. Mihovilovic、Steffen Hering

  DOI：10.1021/jm5002277

  日期：2014.7.10

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.