1-溴-4-甲基-3-戊烯-2-酮 | 49566-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-溴-4-甲基-3-戊烯-2-酮
• 英文名称: bromomethyl mesityloxide
• 英文别名: 1-bromo-4-methyl-3-pentene-2-one；1-bromo-4-methyl-pent-3-en-2-one；1-Bromo-4-methyl-3-penten-2-one；1-bromo-4-methylpent-3-en-2-one
• CAS: 49566-72-5
• 化学式: C₆H₉BrO
• 分子量: 177.041
• InChiKey: ZDGHPWNIHFBZIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-溴-4-甲基-3-戊烯-2-酮 在 potassium carbonate 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 [(2S)-1-[(1-benzyl-5,5-dimethyl-4H-pyrazol-3-yl)methyl]pyrrolidin-2-yl]-diphenylmethanol
  参考文献：
  名称：

  A New Class of Modular Chiral Ligands with Fluxional Groups

  摘要：

  In ligand design for asymmetric catalysis, the usual norm is to derive the face shielding elements from a chiral source. New ligands in which the face shielding is determined by fluxional groups are introduced. Their design, modular synthesis, and experiments to demonstrate the significance of the fluxional groups are discussed. The advantage is that the fluxional groups, introduced at a later stage, allow for simple tuning of the face shielding group.

  DOI：

  10.1021/ja035979d
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 在 四乙基对甲苯磺酸铵 、 三氟乙酸 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 以67%的产率得到1-溴-4-甲基-3-戊烯-2-酮
  参考文献：
  名称：

  α′-Bromination of α,β-unsaturated ketones by an electrochemical procedure

  摘要：

  提出了一种新颖而直接的方法，通过在可变电流密度下对底物-CF3CO2H-CuBr-Et4NOTs-MeCN体系进行电解，实现了α,β-不饱和酮的区域选择性α'-溴化。

  DOI：

  10.1039/c39910001418

文献信息

• Reaction of 1-Nitroso-2-naphthols with α-Functionalized Ketones and Related Compounds: The Unexpected Formation of Decarbonylated 2-Substituted Naphtho[1,2-<i>d</i>][1,3]oxazoles
  作者：Nayyef Aljaar、Chandi C. Malakar、Jürgen Conrad、Wolfgang Frey、Uwe Beifuss

  DOI：10.1021/jo3022956

  日期：2013.1.4

  Reactions between 1-nitroso-2-naphthols and α-functionalized ketones such as α-bromo-, α-chloro-, α-mesyloxy-, α-tosyloxy-, and α-hydroxy ketones under basic conditions delivered 2-substituted naphtho[1,2-d][1,3]oxazoles in a single synthetic operation. The product formation was accompanied by the unexpected loss of the C═O group from the α-functionalized ketones. With aryl bromides, allyl bromides

  1-亚硝基-2-萘与α-官能化酮如α-溴代，α-氯代，α-甲氧基，α-甲苯磺酰基和α-羟基酮之间的反应在碱性条件下产生了2-取代的萘并[一次合成操作中的1,2- d ] [1,3]恶唑。产物的形成伴随有α-官能化酮中C═O基团的意外损失。以芳基溴化物，烯丙基溴化物，α-溴二酮，α-溴氰化物，α-溴酸酯和α-溴酮酸酯为底物，还观察到了萘并[1,2- d ] [1,3]恶唑的形成。在回流下在1,2-二氯乙烷或乙腈中进行转化，得到相应的萘并恶唑，产率在52％至85％之间。
• Contribution to the bromination of conjugate unsaturated ketones
  作者：V. Calo'、L. Lopez、G. Pesce、P.E. Todesco

  DOI：10.1016/s0040-4020(01)83408-6

  日期：1973.1

  Selective bromination of α,β-unsaturated ketones has been achieved by the action of 2,4,4,6-tetrabromocyclohexa-2,5-dienone. The stereochemistry, conformation and relative stability of the bromination products of some steroidic unsaturated ketones have been also determined.

  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。
• 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 cyclic allyl vinyl ethers using Pt(II)-catalyzed isomerization of oxo-alkynes
  作者：Zezhou Wang、Xi Lin、Rudy L. Luck、Garrett Gibbons、Shiyue Fang

  DOI：10.1016/j.tet.2009.01.065

  日期：2009.3

  Several alkynyl epoxides and one alkynyl allyl alcohol were isomerized to cyclic allyl vinyl ethers (3,4-dihydro-2H-1,4-oxazines) using PtCl2 as the catalyst. Three of these allyl vinyl ethers were converted to 2-hydroxymorpholine derivatives by hydrolysis and two were converted to piperidine derivatives by thermal Claisen rearrangement.

  使用PtCl 2作为催化剂，将几种炔基环氧化物和一种炔基烯丙醇异构化为环状烯丙基乙烯基醚（3,4-二氢-2 H -1,4-恶嗪）。这些烯丙基乙烯基醚中的三种通过水解转化为2-羟基吗啉衍生物，而两种通过热克莱森重排转化为哌啶衍生物。
• Grundke, Guenter; Keese, Wolfgang; Rimpler, Manfred, Chemische Berichte, 1985, vol. 118, # 9, p. 4288 - 4291
  作者：Grundke, Guenter、Keese, Wolfgang、Rimpler, Manfred

  DOI：——

  日期：——