(1E,4E)-hexa-1,4-dien-3-one | 10575-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,4E)-hexa-1,4-dien-3-one
• 英文别名: (4E)-hexa-1,4-dien-3-one；prop-1-enyl vinyl ketone；hexa-1,4-dien-3-one；2,5-hexadienone；crotyl vinyl ketone；hexa-1,4t-dien-3-one；(E)-hexa-1,4-dien-3-one
• CAS: 10575-36-7
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: ZMYSGNXLIXWNDV-HWKANZROSA-N

物化性质

• 沸点：
  128.8±9.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1E,4E)-hexa-1,4-dien-3-one 在 poly(3,4-ethylenedioxythiophene) by electrochemical oxidation of 3,4-ethylenedioxythiophene 作用下， 以 甲苯 为溶剂， 以43%的产率得到3-甲基-2-环戊烯-1-酮
  参考文献：
  名称：

  Polymer-Mediated Reactions. A Nazarov-Like Cyclization

  摘要：

  The polymer PEDOT+ mediates a Nazarov-like cyclization of dienones, in an heterogeneous system and in hydrocarbon solvents. The polymer-mediated reactions show clear differences in product formation when compared to the same reaction with tosic acid, or when compared to reports in the literature. Comparable or improved yields are observed, as well as the ability to give a Nazarov product in cases where treatment with acid fails to give cyclization, or leads to an undesirable rearrangement. In addition, the ability to recycle the polymer makes this a potentially useful protocol for an important organic chemical reaction.

  DOI：

  10.1055/s-0030-1261194
• 作为产物：
  描述：

  乙烯基三甲基硅烷 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.75h， 以100%的产率得到(1E,4E)-hexa-1,4-dien-3-one
  参考文献：
  名称：

  [EN] (PIPERIDINYLOXY)PHENYL, (PIPERIDINYLOXY)PYRIDINYL, (PIPERIDINYLSULFANYL)PHENYL AND (PIPERIDINYLSULFANYL)PYRIDINYL COMPOUNDS AS 5-HT1F AGONISTS
  [FR] COMPOSES (PIPERIDINYLOXY)PHENYLE, (PIPERIDINYLOXY)PYRIDINYLE, (PIPERIDINYLSULFANYL)PHENYLE ET (PIPERIDINYLSULFANYL)PYRIDINYLE UTILISES COMME AGONISTES DES RECEPTEURS 5-HT1F

  摘要：

  本发明涉及公式1的化合物及其药用可接受的酸盐。本发明的化合物可用于激活5-HTIF受体，抑制神经蛋白外渗，并用于治疗或预防哺乳动物，尤其是人类的偏头痛。

  公开号：

  WO2004094380A1

文献信息

• BENZOFURO[3,2-c] PYRIDINES AND RELATED ANALOGS AS SEROTONIN SUB-TYPE 6 (5-HT6) MODULATORS FOR THE TREATMENT OF OBESITY, METABOLIC SYNDROME, COGNITION AND SCHIZOPHRENIA
  申请人：GUZZO Peter R.

  公开号：US20120184531A1

  公开（公告）日：2012-07-19

  The present invention relates to benzofuro[3,2-c]pyridine and azepine analogs as serotonin sub-type 6 (5-HT 6 ) modulators, pharmaceutical compositions including these compounds, methods of preparation, and use thereof. These compounds are useful in the treatment of central nervous system disorders including obesity, metabolic syndrome, cognition, schizophrenia, attention deficit hyperactivity disorder, bipolar disorder, rare and orphan diseases, and sleep disorders. The subject compounds have the structure of formula (I) with the substituents being described herein.

  本发明涉及苯并呋喃[3,2-c]吡啶和氮杂环庚烯类似物作为5-羟色胺亚型6（5-HT6）调节剂，包括这些化合物的药物组合物，其制备方法以及使用方法。这些化合物在治疗包括肥胖、代谢综合征、认知障碍、精神分裂症、注意力缺陷多动障碍、躁郁症、罕见和孤儿疾病以及睡眠障碍在内的中枢神经系统疾病中是有用的。所述化合物具有如下式（I）的结构，其中所述取代基在此处描述。
• PYRAZOLO PYRIMIDINE DERIVATIVES
  申请人：MILTZ Wolfgang

  公开号：US20120252778A1

  公开（公告）日：2012-10-04

  The present invention relates to pyrazolo pyrimidine derivatives, to methods of preparing these, to combinations and pharmaceutical composition comprising these, and to their use in the treatment of diseases and disorders which may for example involve autoimmune diseases, angiogenesis, pain, and/or inflammatory diseases.

  本发明涉及吡唑并嘧啶衍生物，涉及制备这些衍生物的方法，涉及包含这些衍生物的组合物和药物组合物，以及它们在治疗可能涉及自身免疫疾病、血管生成、疼痛和/或炎症性疾病的疾病和紊乱中的用途。
• Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation–Michael–aldol cascade
  作者：John W. Ward、Karen Dodd、Caroline L. Rigby、Chris De Savi、Darren J. Dixon

  DOI：10.1039/b924637a

  日期：——

  An efficient, stereoselective Michael–aldol cascade for the one-pot construction of the perhydro indol-2-one bicyclic ring system using an acetate protected doubly-activated pyrrole-2-one pro-nucleophile and α,β-unsaturated carbonyl compounds has been developed. Initiated by a methoxide deacetylation in methanol at room temperature, the cascade is easy to perform, stereoselective, efficient and broad in scope to this synthetically relevant structure.

  已开发出一种高效、立体选择性迈克尔-阿尔多级联反应，用于使用乙酸酯保护的双活化吡咯-2-酮亲核前体和α,β-不饱和羰基化合物，在一锅法中构建全氢吲哚-2-酮双环系统。该级联反应由甲醇中的甲醇脱乙酰基反应在室温下启动，易于操作，具有立体选择性，效率高，适用范围广，可用于合成相关结构。
• Benzofuro[3,2-c] pyridines and related analogs as serotonin sub-type 6 (5-HT6) modulators for the treatment of obesity, metabolic syndrome, cognition and schizophrenia
  申请人：Guzzo Peter R.

  公开号：US09067949B2

  公开（公告）日：2015-06-30

  The present invention relates to benzofuro[3,2-c]pyridine and azepine analogs as serotonin sub-type 6 (5-HT6) modulators, pharmaceutical compositions including these compounds, methods of preparation, and use thereof. These compounds are useful in the treatment of central nervous system disorders including obesity, metabolic syndrome, cognition, schizophrenia, attention deficit hyperactivity disorder, bipolar disorder, rare and orphan diseases, and sleep disorders. The subject compounds have the structure of formula (I) with the substituents being described herein.

  本发明涉及苯并呋喃[3,2-c]吡啶和氮杂七环类似物作为血清素亚型6（5-HT6）调节剂，包括这些化合物的制药组合物，制备方法及其用途。这些化合物在治疗中枢神经系统疾病，包括肥胖症，代谢综合征，认知，精神分裂症，注意力缺陷多动障碍，双相情感障碍，罕见和孤儿疾病以及睡眠障碍方面非常有用。所述化合物具有式（I）的结构，其中取代基在此描述。
• Methyl-substitution of an iminohydantoin spiropiperidine β-secretase (BACE-1) inhibitor has a profound effect on its potency
  作者：Melissa Egbertson、Georgia B. McGaughey、Steven M. Pitzenberger、Shaun R. Stauffer、Craig A. Coburn、Shawn J. Stachel、Wenjin Yang、James C. Barrow、Lou Anne Neilson、Melody McWherter、Debra Perlow、Bruce Fahr、Sanjeev Munshi、Timothy J. Allison、Katharine Holloway、Harold G. Selnick、ZhiQiang Yang、John Swestock、Adam J. Simon、Sethu Sankaranarayanan、Dennis Colussi、Katherine Tugusheva、Ming-Tain Lai、Beth Pietrak、Shari Haugabook、Lixia Jin、I.-W. Chen、Marie Holahan、Maria Stranieri-Michener、Jacquelynn J. Cook、Joseph Vacca、Samuel L. Graham

  DOI：10.1016/j.bmcl.2015.06.082

  日期：2015.11

  The IC50 of a beta-secretase (BACE-1) lead compound was improved similar to 200-fold from 11 mu M to 55 nM through the addition of a single methyl group. Computational chemistry, small molecule NMR, and protein crystallography capabilities were used to compare the solution conformation of the ligand under varying pH conditions to its conformation when bound in the active site. Chemical modification then explored available binding pockets adjacent to the ligand. A strategically placed methyl group not only maintained the required pKa of the piperidine nitrogen and filled a small hydrophobic pocket, but more importantly, stabilized the conformation best suited for optimized binding to the receptor. (C) 2015 Elsevier Ltd. All rights reserved.