bromomethyl styryl ketone | 22422-16-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: bromomethyl styryl ketone
• 英文别名: 1-bromo-4-phenylbut-3-en-2-one
• CAS: 22422-16-8
• 化学式: C₁₀H₉BrO
• 分子量: 225.085
• InChiKey: LDEBGMOZLPUFEE-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  128-131 °C(Press: 1 Torr)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  bromomethyl styryl ketone 在 sodium hydroxide 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 2-[(E)-1-hydroxy-3-phenylallylidene]-4-methylcyclopent-4-ene-1,3-dione
  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：

  苄叉丙酮 在 盐酸 、 四溴环己二烯-1-酮 作用下， 生成 bromomethyl styryl ketone
  参考文献：
  名称：

  对共轭不饱和酮溴化的贡献：α，β-不饱和溴代酮的合成

  摘要：

  通过2,4,4,6-四溴环己基-2,5-二烯酮的作用已经实现了α，β-不饱和酮的选择性溴化。还确定了一些甾族不饱和酮的溴化产物的立体化学，构象和相对稳定性。

  DOI：

  10.1016/s0040-4020(01)83408-6

文献信息

• Base-Mediated Tandem Reaction Consisting of an Acyl Shift Strategy Leading to 4,5-Disubstiuted Furan-2(5H)-ones
  作者：Yong Lei、Zhi-Qiang Wang、Ye-Xiang Xie、Shang-Ci Yu、Bo-Xiao Tang、Jin-Heng Li

  DOI：10.1002/adsc.201000762

  日期：2011.1.10

  The first example of the synthesis of 4,5‐disubstiuted furan‐2(5H)‐ones by base‐mediated tandem acyl shift/cyclization/decarbonylation reactions of aroylmethyl 2‐alkynoates has been developed. This new and inexpensive tandem route allows both a CO bond and a Csp3Csp2 bond forming in one step involving an unprecedented acyl rearrangement process.

  已经开发出通过碱介导的芳烷基2-炔基酸酯的串联酰基转移/环化/去羰基化反应合成4,5-二取代的呋喃-2（5 H）-ones的第一个例子。这种新的和廉价的直通联接路由允许两个碳 O键和C的SP 3  Ç SP 2键在一个步骤涉及了前所未有的酰基重排处理形成。
• Synthesis of <i>N</i>-Formyl-2-benzoyl Benzothiazolines, 2-Substituted Benzothiazoles, and Symmetrical Disulfides from <i>N</i>-Phenacylbenzothiazolium Bromides
  作者：Subas Chandra Sahoo、Subhas Chandra Pan

  DOI：10.1021/acs.orglett.9b01990

  日期：2019.8.16

  An unusual aerobic hydrolysis-cascade reaction has been developed with N-phenacylbenzothiazolium bromides by treatment with organic and inorganic base. The corresponding N-formyl-2-benzoyl benzothiazoline and 2-substituted benzothiazole products were obtained in moderate to good yields under mild reaction conditions. Also, symmetrical disulfide was formed when keto group was replaced with ester. The

  通过用有机碱和无机碱处理，N-苯甲酰基苯并噻唑鎓溴化物已发展出一种不寻常的好氧水解-级联反应。在温和的反应条件下，以中等至良好的产率获得了相应的N-甲酰基-2-苯甲酰基苯并噻唑啉和2-取代的苯并噻唑产物。另外，当酮基被酯取代时，形成对称的二硫键。反应的范围是相当宽的耐受性芳基，杂芳基和烷基。
• Synthesis of 2-alkenyl-3-hydroxyquinolin-4(1 H )-ones as promising antimicrobial and fluorescent agents
  作者：Radim Horák、Lubomír Kvapil、Kamil Motyka、Ludmila Slaninová、Martin Grepl、Kamil Kořistek、Miroslav Urbášek、Pavel Hradil、Miroslav Soural

  DOI：10.1016/j.tet.2017.12.010

  日期：2018.1

  2-Alkenyl-3-hydroxyquinolin-4(1H)-ones were prepared by the rearrangement of anthranilic acid esters synthesized by two alternative methods. The prepared derivatives were screened for their antimicrobial activities against representative Gram-positive and Gram-negative bacteria, displaying notable minimum inhibitory concentration values against specific strains. The emission spectra of the target quinolines

  通过重排由两种替代方法合成的邻氨基苯甲酸酯制备2-烯基-3-羟基喹啉-4（1 H）-one。筛选制备的衍生物对代表性革兰氏阳性和革兰氏阴性细菌的抗菌活性，显示出对特定菌株的显着最小抑菌浓度值。目标喹啉的发射光谱显示出两个分离良好的发射带，并且在相对较高的值下检测到所选化合物的最大激发波长。
• Synthesis of calythrone and related cyclopentene-1,3-diones via rearrangement of 4-ylidenebutenolides
  作者：Nicholas G. Clemo、David R. Gedge、Gerald Pattenden

  DOI：10.1039/p19810001448

  日期：——

  Treatment of 4-ylidenebutenolides with sodium methoxide in methanol results in rearrangement to the corresponding cyclopentene-1,3-diones in high yield. The general method is applied in a synthesis of calythrone [(1) from (18)] from Calythrix tetragona, and the related cyclopentene-1,3-diones [(15) from (14); (25) from (24); (27) from (26); (33) from (32); and (37) from (36)].

  在甲醇中用甲醇钠处理4-亚甲基丁烯内酯导致高产率地重排为相应的环戊烯-1,3-二酮。该通用方法适用于由四叶萼花萼（Calythrix tetragona）和相关的环戊烯-1,3-二酮[（14）的（15）; （25）来自（24）；（27）来自（26）；（33）来自（32）；和（36）中的（37）]。
• Rhodium-Catalyzed C–H Activation of Phenacyl Ammonium Salts Assisted by an Oxidizing C–N Bond: A Combination of Experimental and Theoretical Studies
  作者：Songjie Yu、Song Liu、Yu Lan、Boshun Wan、Xingwei Li

  DOI：10.1021/ja511796h

  日期：2015.2.4

  and the coupling with unactivated alkenes such as styrenes and aliphatic olefins gave ortho-olefinated acetophenoes. In both systems the reactions proceeded with a broad scope, high efficiency, and functional group tolerance. Moreover, efficient one-pot coupling of diazo esters has been realized starting from α-bromoacetophenones and triethylamine. The reaction mechanism for the coupling with diazo

  由氧化导向基团辅助的 Rh(III) 催化的 CH 活化已演变为用于构建杂环的温和且氧化还原经济的策略。尽管取得了成功，但这些偶联系统目前仅限于裂解氧化性 NO 或 NN 键。允许互补碳环合成的氧化性 CN 键的断裂是前所未有的。在本文中，具有氧化性 CN 键的 α-铵苯乙酮被设计为在氧化还原中性条件下 Rh(III) 催化 CH 活化的底物。与α-重氮酯偶联得到苯并环戊酮，与未活化烯烃如苯乙烯和脂肪族烯烃偶联得到邻位烯化苯乙酮。在这两个系统中，反应都以广泛的范围、高效率和官能团耐受性进行。而且，从α-溴苯乙酮和三乙胺开始，已经实现了重氮酯的有效一锅偶联。通过实验和理论相结合的方法研究了与重氮酯偶联的反应机理。特别是，DFT 研究仔细检查了三种不同的机制途径，这表明 CH 活化是通过 C 键合烯醇化物辅助的协同金属化-去质子化机制发生的，并且是限速的。在随后的 CC 形成步骤中，最低能量途