(Z)-4-iodo-4-hexen-3-one | 134891-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-iodo-4-hexen-3-one
• 英文别名: (4Z)-4-iodo-4-hexen-3-one；(Z)-4-iodohex-4-en-3-one
• CAS: 134891-14-8
• 化学式: C₆H₉IO
• 分子量: 224.041
• InChiKey: HBCMYTHJQSSJPJ-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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

• 作为产物：
  描述：

  (E)-4-己烯-3-酮 在 4-二甲氨基吡啶 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以90%的产率得到(Z)-4-iodo-4-hexen-3-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

• Concerning the formations of α-iodoenones
  作者：Pakorn Bovonsombat、Geetha J. Angara、Edward Mc Nelis

  DOI：10.1016/0040-4039(94)85005-4

  日期：1994.9

  The formations of α-iodoenones from secondary alkynols with NIS/HTIB (cat.), tertiary alkynols with I2/PDC and enones with I2/pyridine have been compared. In the latter two reactions the PDC and the pyridine have been found to be catalytic.

  比较了由具有NIS / HTIB的仲炔醇（目录号），具有I 2 / PDC的叔炔醇和具有I 2 /吡啶的烯酮形成的α-碘烯酮。在后两个反应中，发现PDC和吡啶具有催化作用。
• 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。
• SYNTHESIS OF ALPHA-HALO ENONES AND ENALS
  申请人：Zhang Liming

  公开号：US20110021806A1

  公开（公告）日：2011-01-27

  A method for preparing an α-halo enal or enone from an unprotected propargyl alcohol and an electrophilic halogen source catalyzed by the combination of a gold catalyst complex and a metal co-catalyst complex is disclosed. The method can be further enhanced by addition of an additive that facilitates suppression of a des-halo derivative.

  本发明公开了一种通过金催化剂配合金属共催化剂，从未保护的丙炔醇和电泳卤素源制备α-卤代烯醇或烯酮的方法。该方法可以通过添加有助于抑制去卤代衍生物的添加剂来进一步增强。
• Formations of α-Iodoenones by Iodine and Catalytic Amounts of Amines
  作者：Elsa Djuardi、Pakorn Bovonsombat、Edward Mc Nelis

  DOI：10.1080/00397919708004113

  日期：1997.7

  Iodine and catalytic amounts of amines in a variety of solvents react with cyclic and acyclic enones to afford the corresponding alpha-iodoenones.
• α-Haloenones from secondary alkynols
  作者：Geetha J. Angara、Edward McNelis

  DOI：10.1016/s0040-4039(00)71246-9

  日期：1991.5

  alpha-Iodoenones and alpha-bromoenones are formed from secondary alkynols by the use of the appropriate N-halosuccinimide and a catalytic amount of certain Lewis acids. For example, 3-hexyn-2-ol (1) was converted to (Z)-4-iodo-4-hexen-3-one (2) in 85-95% yields with an equimolar quantity of NIS and tenth molar (hydroxy (toxyloxy) iodo) benzene (3) in methanol or 1-methyl-2-pyrrolididone.