(E)-1-bromo-4-(furan-2-yl)but-3-en-2-one | 923025-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-1-bromo-4-(furan-2-yl)but-3-en-2-one
• 英文别名: (E)-1-bromo-4-(fur-2-yl)-but-3-en-2-one
• CAS: 923025-55-2
• 化学式: C₈H₇BrO₂
• 分子量: 215.046
• InChiKey: WQNYIEVLMKADMF-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-4-(furan-2-yl)but-3-en-2-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 (5E)-5-[(E)-4-(furan-2-yl)-2-oxobut-3-enylidene]-3-methylfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

  摘要：

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.

  DOI：

  10.1021/jm061123i
• 作为产物：
  描述：

  (E)-4-(furan-2-yl)but-3-en-2-one 在 lithium diisopropyl amide 、 三甲基氯硅烷 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 以59%的产率得到(E)-1-bromo-4-(furan-2-yl)but-3-en-2-one
  参考文献：
  名称：

  N-杂环卡宾催化（5 + 1）环开发乙烯基二价阴离子合成策略

  摘要：

  共轭受体的直接极性反转提供了一个有价值的进入均烯酸酯的途径。已经开发出了N-杂环卡宾（NHC）催化的反应，其中β-未取代的共轭受体经历了均烯酸酯形成和C-C键形成两次。具体而言，全碳（5 + 1）环空给出了一系列单环和双环环己酮（31个示例）。在第一个环族中，束缚在二乙烯基酮上的β-未取代的丙烯酸酯会进行环异构化，从而提供六氢茚和四氢化萘。在第二部分中，部分未束缚的底物经历分子间（5 + 1）环合反应，其中涉及二聚化，然后进行环异构化。尽管前者不可能实现对映选择性，但后者被证明是可行的，从而可以生产出高水平的对映体纯度的环己酮（大多数> 95：5 er）和非对映选择性（> 20：1 dr）。还报道了衍生化和机理研究。

  DOI：

  10.1002/anie.201905475

文献信息

• Efficient Control of π-Alkyne and Vinylidene Complex Pathways for the W(CO)₅(L)-Catalyzed Synthesis of Two Types of Nitrogen-Containing Bicyclic Compounds
  作者：Yuji Onizawa、Hiroyuki Kusama、Nobuharu Iwasawa

  DOI：10.1021/ja0782605

  日期：2008.1.1

  2-azabicyclo[3.3.0]octanes were obtained in good yield via pi-alkyne complexes. On the other hand, treatment of the same substrates with a catalytic amount of W(CO)6 in the presence of n-Bu3N under the same reaction conditions gave 3-azabicyclo[3.3.0]octanes in good yield exclusively via vinylidene complexes. Thus, the pi-alkyne and vinylidene complex pathways are easily controlled by using a catalytic amount

  当在系链中含有 NMs 部分的 omega-炔二烯醇甲硅烷基醚在光照射下用催化量的 W(CO)6 处理​​时，2-氮杂双环 [3.3.0] 辛烷通过 pi-炔配合物以良好的产率获得。另一方面，在相同反应条件下，在 n-Bu3N 存在下用催化量的 W(CO)6 处理​​相同的底物，仅通过亚乙烯基配合物以良好的产率得到 3-氮杂双环 [3.3.0] 辛烷。因此，通过使用催化量的 W(CO)5(L) 和胺，可以轻松控制 pi-炔烃和亚乙烯基络合物途径。
• N‐Heterocyclic Carbene Catalyzed (5+1) Annulations Exploiting a Vinyl Dianion Synthon Strategy
  作者：Xuan B. Nguyen、Yuji Nakano、Nisharnthi M. Duggan、Lydia Scott、Martin Breugst、David W. Lupton

  DOI：10.1002/anie.201905475

  日期：2019.8.12

  Direct polarity inversion of conjugate acceptors provides a valuable entry to homoenolates. N‐heterocyclic carbene (NHC) catalyzed reactions, in which β‐unsubstituted conjugate acceptors undergo homoenolate formation and C−C bond formation twice, have been developed. Specifically, the all‐carbon (5+1) annulations give a range of mono‐ and bicyclic cyclohexanones (31 examples). In the first family of

  共轭受体的直接极性反转提供了一个有价值的进入均烯酸酯的途径。已经开发出了N-杂环卡宾（NHC）催化的反应，其中β-未取代的共轭受体经历了均烯酸酯形成和C-C键形成两次。具体而言，全碳（5 + 1）环空给出了一系列单环和双环环己酮（31个示例）。在第一个环族中，束缚在二乙烯基酮上的β-未取代的丙烯酸酯会进行环异构化，从而提供六氢茚和四氢化萘。在第二部分中，部分未束缚的底物经历分子间（5 + 1）环合反应，其中涉及二聚化，然后进行环异构化。尽管前者不可能实现对映选择性，但后者被证明是可行的，从而可以生产出高水平的对映体纯度的环己酮（大多数> 95：5 er）和非对映选择性（> 20：1 dr）。还报道了衍生化和机理研究。
• Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues
  作者：K. Suresh Babu、Xing-Cong Li、Melissa R. Jacob、Qifeng Zhang、Shabana I. Khan、Daneel Ferreira、Alice M. Clark

  DOI：10.1021/jm061123i

  日期：2006.12.1

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.