2,3,4,7-tetrahydrooxepin-2-one | 87256-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,3,4,7-tetrahydrooxepin-2-one
• 英文别名: 4,5-dehydro ε-lactone；(Z)-4-Hexenolide；4,7-Dihydrooxepin-2(3H)-one；5,6-dihydro-2H-oxepin-7-one
• CAS: 87256-39-1
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: UEBKKQBYJFXHRI-UHFFFAOYSA-N

物化性质

• 沸点：
  235.4±29.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,7-tetrahydrooxepin-2-one 在 aluminum tris(2,6-diphenylphenoxide) 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 生成 5-乙炔二氢-2(3H-)-呋喃酮
  参考文献：
  名称：

  Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

  摘要：

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

  DOI：

  10.1021/ol8022227
• 作为产物：
  描述：

  allyl 4-pentenoate 在 aluminum tris(2,6-diphenylphenoxide) 、 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 8.25h， 以60%的产率得到2,3,4,7-tetrahydrooxepin-2-one
  参考文献：
  名称：

  Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

  摘要：

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

  DOI：

  10.1021/ol8022227

文献信息

• [EN] COMPOUNDS USEFUL FOR TREATING NEURODEGENERATIVE DISORDERS<br/>[FR] COMPOSÉS UTILES POUR LE TRAITEMENT DE TROUBLES NEURODÉGÉNÉRATIFS
  申请人：SATORI PHARMACEUTICALS INC

  公开号：WO2011109657A1

  公开（公告）日：2011-09-09

  As described herein, the present invention provides compounds useful for treating or lessening the severity of a neurodegenerative disorder. The present invention also provides methods of treating or lessening the severity of such disorders wherein said method comprises administering to a patient a compound of the present invention, or composition thereof. Said method is useful for treating or lessening the severity of, for example, Alzheimer's disease.

  如本文所述，本发明提供了用于治疗或减轻神经退行性疾病严重程度的化合物。本发明还提供了治疗或减轻此类疾病严重程度的方法，其中所述方法包括向患者施用本发明的化合物或其组合物。该方法适用于治疗或减轻例如阿尔茨海默病等疾病的严重程度。
• [EN] COMPOUNDS USEFUL FOR TREATING NEURODEGENERATIVE DISORDERS<br/>[FR] COMPOSÉS UTILES POUR TRAITEMENT DE TROUBLES NEURODÉGÉNÉRATIFS
  申请人：SATORI PHARMACEUTICALS INC

  公开号：WO2013036684A1

  公开（公告）日：2013-03-14

  The present invention provides compounds of formula I: or a pharmaceutically acceptable salt thereof, wherein each of the variables listed above are as defined and described herein, compositions thereof, and methods of using the same.

  本发明提供了式I的化合物：或其药学上可接受的盐，上述列出的每个变量如本文所定义和描述的那样，以及其组合物和使用方法。
• [EN] BENZAMIDE AND NICOTINAMIDE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] BENZAMIDE ET COMPOSÉS DE NICOTINAMIDE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ONCOTARTIS INC

  公开号：WO2015100322A1

  公开（公告）日：2015-07-02

  The present disclosure provides benzamide and nicotinamide compounds and pharmaceutical uses of the compounds. The compounds can be used to treat, for example, cancers such hematopoietic cancers (e.g., leukemia). The preferred compounds of the invention contain a phenylethynyl moiety as well as an amine-based heterocyclyl or heteroaryl moiety attached to the benzamide or nicotinamide compound.

  本公开提供苯甲酰胺和烟酰胺化合物以及这些化合物的药用。这些化合物可用于治疗，例如，血液肿瘤等血液肿瘤（如白血病）。本发明的优选化合物包含苯乙炔基团以及连接到苯甲酰胺或烟酰胺化合物的胺基杂环基团或杂芳基团。
• [EN] FUSED INDOLE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS INDOLE FUSIONNÉS ET LEURS MÉTHODES D'UTILISATION
  申请人：OBSCHESTVO S OGRANICHENNOY OTVETSTVENNOST YU PANACELA LABS

  公开号：WO2015050472A1

  公开（公告）日：2015-04-09

  The invention relates to fused indole compounds of formula (I) that can be used for treating microbial infections, in particular, fungal infections, and selectively kill cancer cells.

  这项发明涉及公式（I）的融合吲哚化合物，可用于治疗微生物感染，特别是真菌感染，并选择性地杀灭癌细胞。
• Highly Regio- and Stereoselective Ring-Opening Reaction of γ-Alkenyl-γ-butyrolactones with Allylsilanes in the Presence of Trimethyloxonium Salt Leading to Methyl 4,8-Alkadienoates
  作者：Masatoshi Kawashima、Tamotsu Fujisawa

  DOI：10.1246/bcsj.61.4051

  日期：1988.11

  The reaction of γ-alkenyl-γ-butyrolactones with allylic trimethylsilanes in the presence of trimethyloxonium tetrafluoroborate proceeded regio- and stereoselectively with an allylic rearrangement of the substrate to afford methyl (E)-4,8-alkadienoates in high yields. On the other hand, the ring opening of 4-hexen-6-olide afforded exclusively methyl (Z)-4,8-alkadienoates in high yields. The synthetic utility of the reaction was demonstrated by the short step synthesis of β-sinensal and β-farnesene.

  γ-烯基-γ-丁内酯与烯丙基三甲基硅烷在三甲基氧鎓四氟硼酸盐存在下的反应，经过区域和立体选择性，底物发生烯丙重排，生成了高产率的甲基 (E)-4,8-烯二酸酯。另一方面，4-己烯-6-内酯的开环反应则专门生成高产率的甲基 (Z)-4,8-烯二酸酯。这一反应的合成实用性通过β-辛烯醛和β-法尼烯的短步合成得到了验证。