2-iodo-1-phenylprop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-iodo-1-phenylprop-2-en-1-one
• 化学式: C₉H₇IO
• 分子量: 258.058
• InChiKey: PKXRITOHVVQSLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  N-cyclohexylpicolinamide 、 2-iodo-1-phenylprop-2-en-1-one 在 叔丁基对苯醌 、 palladium diacetate 、 silver carbonate 作用下， 反应 24.0h， 以47%的产率得到
  参考文献：
  名称：

  2-叔丁基-1,4-苯醌促进N-吡啶甲酰基环烷基胺与烯基碘的Pd催化亚甲基γ-C(sp 3 )-H烯基化

  摘要：

  2-叔丁基-1,4-苯醌（TBBQ）促进了乙酸钯（II）催化的N-吡啶甲基环烷基胺的亚甲基sp 3 γ-碳-氢键与烯基碘在碳酸银存在下的烯基化. N-吡啶甲酰基环己胺与链烯基碘的这种官能化仅以高达82%的产率提供一系列顺式-3-(1-链烯基) -N-吡啶甲酰基环己胺。相比之下，TBBQ 促进的大环底物N-吡啶甲酰基环十二胺的烯基化仅产生反式-3-(1-烯基) -N-吡啶甲酰基环十二胺作为单烯基化产物，产率高达 52%。有趣的是，由于底物环尺寸增加，产物的立体选择性发生逆转。这是反式-γ C H 烯基化的第一个例子。

  DOI：

  10.1016/j.tetlet.2021.153130
• 作为产物：
  描述：

  1-苯基-2-丙烯基-1-酮 在 奎宁环 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以92%的产率得到2-iodo-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  A Convenient Protocol for the α-Iodination of α,β-Unsaturated Carbonyl Compounds with I₂ in an Aqueous Medium

  摘要：

  多种环状及非环状的α,β-不饱和羰基化合物，能够专门地在高产率下通过I2在含水THF中经DMAP和奎宁环催化进行α-碘化反应。

  DOI：

  10.1055/s-2005-868495

文献信息

• Direct Synthesis of α-Iodoenones by IPy₂BF₄-Promoted Rearrangement of Propargylic Esters
  作者：Tatiana Suárez-Rodríguez、Ángel L. Suárez-Sobrino、Alfredo Ballesteros

  DOI：10.1021/acs.joc.8b01746

  日期：2018.10.19

  A direct access to α-iodoeones from iodonium ion and propargylic tosylates or acetates is described. Bis(pyridine) iodonium tetrafluoroborate (IPy2BF4, Barluenga’s reagent) promotes the rearrangement of these propargylic alcohol derivatives in mild conditions. The transformation gives β-unsubstituted, β-monosubstituted, and β,β-disubstituted α-iodoenones in high yields. β-Substituted α-iodoenones are

  描述了从碘鎓离子和炔丙基甲苯磺酸盐或乙酸盐直接获得α-碘酮的方法。双（吡啶）四氟硼酸碘鎓盐（IPy 2 BF 4，Barluenga的试剂）在温和条件下促进这些炔丙醇衍生物的重排。该转化以高产率产生β-未取代的，β-单取代的和β，β-二取代的α-碘烯。以优异的（Z）选择性获得β-取代的α-碘烯。
• Catalyst-Free Halogenation of α-Diazocarbonyl Compounds with <i>N</i>-Halosuccinimides: Synthesis of 3-Halooxindoles or Vinyl Halides
  作者：Chaoqun Ma、Dong Xing、Wenhao Hu

  DOI：10.1021/acs.orglett.6b01346

  日期：2016.7.1

  A novel catalyst-free halogenative cyclization of N-aryl diazoamides with N-halosuccinimides (NXS) is reported for the synthesis of 3-halooxindoles through a carbene-free mechanism. N-Aryl diazoamides reacted with NXS under mild and catalyst-free conditions to afford the corresponding 3-halooxindoles in good yields. This transformation is proposed to proceed through diazonium ion formation followed

  据报道，N-芳基重氮酰胺与N-卤代琥珀酰亚胺（NXS）的新型无催化剂卤代环化反应是通过无卡宾机理合成的3-卤代新吲哚。N-芳基重氮酰胺在温和且无催化剂的条件下与NXS反应，以良好的收率得到相应的3-卤代氧代吲哚。建议通过重氮离子形成，然后进行分子内Friedel-Crafts烷基化来进行这种转化。
• Stereoselective Synthesis of Stannyl Enones via Palladium-Catalyzed and Free Radical Hydrostannation of Alkynyl Ketones with Trineophyltin Hydride
  作者：Verónica I. Dodero、Liliana C. Koll、M. Belén Faraoni、Terence N. Mitchell、Julio C. Podestá

  DOI：10.1021/jo035396m

  日期：2003.12.1

  A study on the addition of trineophyltin hydride (1) to alkynones under free radical (AIBN and Et3B) and palladium-catalyzed [(PPh3)(2)PdCl2] conditions is reported. The results obtained indicate that the addition of 1 to eight ynones catalyzed by bis(triphenylphosphine)palladium(II) chloride led in all cases to addition products in very high yields (80-96%). These additions take place with excellent regio- and stereochemistry, leading to the alpha adducts as major products in seven out of the eight cases studied. Also the E adducts, resulting from a syn attack, were the only (seven cases) or the predominant (one case) products. The radical hydrostannations initiated by AIBN of ynones 2-5 with 1 led to addition products in good yields (60-88%); with the more hindered ketones 6 and 7-9 the yields obtained were lower. The radical additions initiated by triethylboron to ynones 2-6 follow a similar pattern but with lower yields; no addition products in the hydrostannation of ynones 7-9 were detected. The new acyl-substituted vinylstannanes, owing to their greater stability compared with that of their tributyl- and trimethylstannyl analogues, can be purified by column chromatography using neutral alumina (in all cases) or silica gel 60 (in most cases) as adsorbents. Full H-1, C-13, and Sn-119 NMR data are given.
• A Convenient Protocol for the α-Iodination of α,β-Unsaturated Carbonyl Compounds with I₂ in an Aqueous Medium
  作者：Marie Krafft、John Cran

  DOI：10.1055/s-2005-868495

  日期：——

  A variety of cyclic and acyclic α,β-unsaturated carbonyl compounds undergo α-iodination exclusively, in high yields, with I2 in aqueous THF catalyzed by DMAP and quinuclidine.

  多种环状及非环状的α,β-不饱和羰基化合物，能够专门地在高产率下通过I2在含水THF中经DMAP和奎宁环催化进行α-碘化反应。
• Pd-catalyzed methylene γ-C(sp3)—H alkenylation of N-picolinoylcycloalkylamines with alkenyl iodides promoted by 2-tert-butyl-1,4-benzoquinone
  作者：Atsushi Seki、Yoshiaki Takahashi

  DOI：10.1016/j.tetlet.2021.153130

  日期：2021.6

  acetate-catalyzed alkenylation of the methylene sp3 γ-carbon-hydrogen bonds of N-picolinoylcycloalkylamines with alkenyl iodides in the presence of silver carbonate was promoted by 2-tert-butyl-1,4-benzoquinone (TBBQ). This functionalization of N-picolinoylcyclohexylamine with alkenyl iodides exclusively provided a range of cis-3-(1-alkenyl)-N-picolinoylcyclohexylamines in up to 82% yield. In contrast, the TBBQ-promoted

  2-叔丁基-1,4-苯醌（TBBQ）促进了乙酸钯（II）催化的N-吡啶甲基环烷基胺的亚甲基sp 3 γ-碳-氢键与烯基碘在碳酸银存在下的烯基化. N-吡啶甲酰基环己胺与链烯基碘的这种官能化仅以高达82%的产率提供一系列顺式-3-(1-链烯基) -N-吡啶甲酰基环己胺。相比之下，TBBQ 促进的大环底物N-吡啶甲酰基环十二胺的烯基化仅产生反式-3-(1-烯基) -N-吡啶甲酰基环十二胺作为单烯基化产物，产率高达 52%。有趣的是，由于底物环尺寸增加，产物的立体选择性发生逆转。这是反式-γ C H 烯基化的第一个例子。