2-(碘乙酰基)呋喃 | 55984-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(碘乙酰基)呋喃
• 英文名称: 2-(iodoacetyl)furan
• 英文别名: 1-(furan-2-yl)-2-iodoethan-1-one；1-(Furan-2-yl)-2-iodoethanone
• CAS: 55984-18-4
• 化学式: C₆H₅IO₂
• 分子量: 236.009
• InChiKey: MFCRVYVWJUKLSX-UHFFFAOYSA-N

物化性质

• 沸点：
  275.3±20.0 °C(Predicted)
• 密度：
  1.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(碘乙酰基)呋喃 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以100%的产率得到
  参考文献：
  名称：

  Synthesis of α-Functionalized Trichloromethylcarbinols

  摘要：

  A new series of alpha-functionalized trichloromethylcarbinols have been synthesized from corresponding alpha-halomethyl ketones, esters, and amides in 48-78% overall yields. Reactivity of nitrates obtained in the first step was dependent on the electron-withdrawing nature of the functional groups, and increases with increasing electron deficiency. Synthetic applications of such trichloromethylcarbinols for the preparation of chloromethyl-alpha-diketones, trichloromethylated dihydrofurans, and enol acetates of alpha-functionalized acid chlorides have been demonstrated. The reaction of these compounds in the Jocic-Reeve reaction was also demonstrated.

  DOI：

  10.1021/acs.joc.5b01547
• 作为产物：
  描述：

  2-乙酰基呋喃 在 碘 、 copper(II) oxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到2-(碘乙酰基)呋喃
  参考文献：
  名称：

  Highly Efficient and Clean Method for Direct α-Iodination of Aromatic Ketones

  摘要：

  在中性反应条件下，芳香酮通过铜(II)氧化物和碘的组合高效转化为相应的α-碘酮。反应机理表明，铜(II)氧化物通过随机自分类发挥多重作用。

  DOI：

  10.1055/s-2007-983880

文献信息

• A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives
  作者：Qun Cai、Yan-Ping Zhu、Yang Gao、Jing-Jing Sun、An-Xin Wu

  DOI：10.1139/cjc-2012-0534

  日期：2013.6

  A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3-dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

  已提出一种简洁高效的策略，可从易得的芳基或杂环芳基甲基酮、吡啶和丙烯腈合成吲哚啉衍生物。机理途径涉及碘化、吡啶铵叶立德合成和1,3-二极环加成的整合。该方案在高产率、操作简便、温和反应条件和易于操作等方面表现出高效性。这种方法为通过新颖串联合成合成吲哚啉衍生物提供了重要补充。
• I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea
  作者：Yan-Ping Zhu、Jing-Jing Yuan、Qin Zhao、Mi Lian、Qing-He Gao、Mei-Cai Liu、Yan Yang、An-Xin Wu

  DOI：10.1016/j.tet.2011.10.074

  日期：2012.1

  A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a–f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds

  开发了一种由易得的甲基酮/不饱和甲基酮和硫脲组成的简洁高效的一锅法，用于在I 2 / CuO介质下合成2-氨基噻唑。该方法可以高度立体选择性地获得4-乙烯基-2-氨基噻唑的电子异构体（5a–f）。所有这些目标分子均通过NMR，HRMS和IR光谱进行了表征。此外，通过X射线晶体学分析进一步确定目标化合物3c和5b。
• Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines
  作者：Mi Lian、Qi Li、Yanping Zhu、Guodong Yin、Anxin Wu

  DOI：10.1016/j.tet.2012.09.056

  日期：2012.11

  A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H2O.

  从简单的酮和1,2-二胺开发了一种新颖的喹喔啉合成方案。此过程通过连续碘化经历了一个逻辑方式双-取代的喹喔啉/ kornblum氧化反应/环化在我的存在2 /的CuO / DMSO中，并通过以单取代的喹喔啉碘化/环化/芳构化中的我的存在2 /的CuO / K 3 PO 4 ·3H 2 O.
• [EN] CF3O-containing enaminoketones and their utilization for the preparation of CF3O-containing pyrazoles<br/>[FR] ÉNAMINOCÉTONES CONTENANT CF3O ET LEUR UTILISATION POUR LA PRÉPARATION DE PYRAZOLES CONTENANT CF3O
  申请人：BAYER IP GMBH

  公开号：WO2013120876A1

  公开（公告）日：2013-08-22

  The present invention pertains to novel enaminoketones containing a CF3O-group, novel pyrazole-derivatives containing a CF3O group as well as to a novel process for their preparation comprising aminoformylation of CF30-ketones and cyclization of the obtained CF30-enaminoketones with hydrazines to trifluoromethoxy pyrazoles.

  这项发明涉及含有CF3O基团的新型烯胺酮，含有CF3O基团的新型吡唑衍生物，以及一种新型制备它们的方法，包括CF30-酮的氨基甲酰化和所得的CF30-烯胺酮与肼环化生成三氟甲氧基吡唑。
• CF3O-containing enaminoketones and their utilization for the preparation of CF3O-containing pyrazoles
  申请人：Bayer CropScience AG

  公开号：EP2628722A1

  公开（公告）日：2013-08-21

  The present invention pertains to novel enaminoketones containing a CF3O-group, novel pyrazole-derivatives containing a CF3O group as well as to a novel process for their preparation comprising aminoformylation of CF3O-ketones and cyclization of the obtained CF3O-enaminoketones with hydrazines to trifluoromethoxy pyrazoles.

  这项发明涉及含有CF3O基团的新型烯胺酮，含有CF3O基团的新型吡唑衍生物，以及一种新型制备它们的方法，包括CF3O酮的氨基甲酰化和所得CF3O烯胺酮与肼的环化反应，形成三氟甲氧基吡唑。