4-bromopent-3-en-2-one | 80356-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromopent-3-en-2-one
• 英文别名: (3Z)-4-Bromo-3-penten-2-one；(Z)-4-bromopent-3-en-2-one
• CAS: 80356-21-4
• 化学式: C₅H₇BrO
• 分子量: 163.014
• InChiKey: SFEGAWKULWWXCA-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-bromopent-3-en-2-one 生成 1,2-戊二烯-4-酮
  参考文献：
  名称：

  SANCHEZ-OBREGON R.; BARRIOS H.; ORTIZ B.; YUSTE F., REV. ROUM. CHIM., 31,(1986) N 7, 709-710

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酮 在 triphenylphosphine dibromide 1:1 addition complex 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以48%的产率得到4-bromopent-3-en-2-one
  参考文献：
  名称：

  Highly efficient syntheses of 3-aryl-2-cycloalken-1-ones and an evaluation of their liquid crystalline properties

  摘要：

  Cycloalkenones are shown to be mesogens and can be synthesised in near quantitative yields by a convergent palladium(0)-catalysed cross-coupling strategy; a 2-methyl group induces a change of phase from smectic to nematic. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00620-3

文献信息

• Lithiation of 3,4-bis(tri-n-butylstannyl)furan: regiospecific synthesis of unsymmetrical 3,4-disubstituted furans
  作者：Yun Yang、Henry N. C. Wong

  DOI：10.1039/c39920001723

  日期：——

  3-(Tri-n-butylstannyl)-4-lithiofuran 2, obtained through tin–lithium exchange from 3,4-bis(tri-n-butylstannyl)furan 1, reacts regiospecifically with various electrophiles to give monosubstituted stannylfurans, which are converted into unsymmetrical 3,4-disubstituted furans utilising Stille's palladium-catalysed coupling reactions.

  3-(三正丁基锡基)-4-锂呋喃2是通过锡-锂交换从3,4-双(三正丁基锡基)呋喃1获得的，它与各种电正体发生区域选择性反应，生成单取代锡呋喃，这些锡呋喃又通过斯蒂尔的钯催化偶联反应转化为非对称的3,4-双取代呋喃。
• Synthesis of β-chloro, β-bromo, and β-iodo α,β-unsaturated ketones
  作者：Edward Piers、John R. Grierson、Cheuk Kun Lau、Isao Nagakura

  DOI：10.1139/v82-033

  日期：1982.1.15

  A new, efficient method for the preparation of β-chloro, β-bromo, and β-iodo α,β-unsaturated ketones is described. The method involves the reaction of β-diketones or α-hydroxymethylenecycloalkanones with triphenylphosphine dihalides in the presence of triethylamine. With the dichloride and dibromide reagents, the reactions are conveniently carried out in benzene at room temperature, while with triphenylphosphine diiodide the reactions are best performed in refluxing acetonitrile (β-diketones) or in acetonitrile–hexamethylphosphoramide (α-hydroxymethylenecycloalkanones). The reaction of triphenylphosphine diiodide – triethylamine with a series of 4-alkyl-1,3-cyclohexanediones provides mainly or exclusively (depending on the size of the alkyl group) 6-alkyl-3-iodo-2-cyclohexen-1-ones, while reaction of this reagent with 2-hydroxymethylenecyclohexanone and 2-hydroxymethylenecyclopentanone affords stereoselectively and regioselectively (E)-2-iodomethylenecyclohexanone and (E)-2-iodomethylenecyclopentanone, respectively.

  描述了一种制备β-氯、β-溴和β-碘α，β-不饱和酮的新的高效方法。该方法涉及β-二酮或α-羟甲基环戊酮与三苯基膦二卤化物在三乙胺存在下的反应。对于二氯化物和二溴化物试剂，反应通常在苯中室温下进行，而对于三苯基膦二碘化物，最好在回流的乙腈（β-二酮）或乙腈-六甲基磷酰胺（α-羟甲基环戊酮）中进行。三苯基膦二碘化物-三乙胺与一系列4-烷基-1,3-环己二酮的反应主要或仅产生（取决于烷基的大小）6-烷基-3-碘-2-环己烯-1-酮，而该试剂与2-羟甲基环己酮和2-羟甲基环戊酮的反应分别选择性地产生（E）-2-碘甲基环己酮和（E）-2-碘甲基环戊酮。
• Regiospecific synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)f
  作者：Yun Yang、Henry N.C. Wong

  DOI：10.1016/s0040-4020(01)85528-9

  日期：1994.1

  3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)furan have been prepared and used successfully as building blocks to lead to various

  制备了3,4-双（三-正丁基锡烷基）呋喃和3-（三-正丁基锡烷基）呋喃，并成功地用作制造各种产品的基础。
• A New Preparative Route to Organic Halides from Alcohols via the Reduction of Polyhalomethanes
  作者：E. Léonel、J. P. Paugam、J. Y. Nédélec

  DOI：10.1021/jo970767i

  日期：1997.10.1
• A New Convenient Synthesis of 1,2-Pentadien-4-one (Acetylallene)
  作者：Gérard Buono

  DOI：10.1055/s-1981-29624

  日期：——