(E)-1,2-diiodo-1-(4-methylphenyl)ethene | 219517-81-4

• 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: (E)-1,2-diiodo-1-(4-methylphenyl)ethene
• 英文别名: (E)-1-(1,2-diiodovinyl)-4-methylbenzene；1-(1,2-diiodovinyl)-4-methylbenzene；(E)-1,2-diiodo-p-methylstyrene；1-[(E)-1,2-diiodoethenyl]-4-methylbenzene
• CAS: 219517-81-4
• 化学式: C₉H₈I₂
• 分子量: 369.972
• InChiKey: QHTUVLMTNLCMAU-RMKNXTFCSA-N

物化性质

• 沸点：
  318.0±41.0 °C(Predicted)
• 密度：
  2.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  氟磺酰基二氟乙酸甲酯 、 (E)-1,2-diiodo-1-(4-methylphenyl)ethene 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到(E)-1-methyl-4-(3,3,3-trifluoro-1-iodoprop-1-en-1-yl)benzene
  参考文献：
  名称：

  A New and Improved Synthesis of trans-1,2-Diiodoalkenes and Their Stereospecific and Highly Regioselective Trifluoromethylation

  摘要：

  Reaction of terminal alkynes with iodine in the presence of CuI (5%) in acetonitrile under reflux for several hours gave the trans-1,2-diiodoalkenes in high yields. The trifluoromethylation of these diiodides using FSO2CF2CO2Me/CuI/DMF proceeded in excellent yields in a stereospecific and highly regioselective manner.

  DOI：

  10.1021/jo9816663
• 作为产物：
  描述：

  Alpha-甲基苯乙烯 在 碘 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1,2-diiodo-1-(4-methylphenyl)ethene
  参考文献：
  名称：

  Synthesis of substituted acetylenes, aryl–alkyl ethers, 2-alkene-4-ynoates and nitriles using heterogeneous mesoporous Pd-MCM-48 as reusable catalyst

  摘要：

  Pd-MCM-48 has been employed as a heterogeneous catalyst for the synthesis of substituted acetylenes via Sonogashira reactions under copper and amine-free reaction conditions. In addition, the catalyst exhibited excellent regioselectivity for primary alcohols towards C-O coupling leading to formation of alkyl aryl ethers in high yields. A green procedure for the stereoselective synthesis of 2-alkene-4-ynoates and nitriles from the reactions of vic-(E)-diiodoalkenes with activated alkenes has also been demonstrated using Pd-MCM-48 catalyst. The catalyst was easily recovered from the reaction mixture by filtration and reused for at least six times with minimal loss of activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.132

文献信息

• Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(<scp>i</scp>) salt
  作者：Dodla S. Rao、Thurpu R. Reddy、Sudhir Kashyap

  DOI：10.1039/c7ob03076b

  日期：——

  An efficient and highly chemoselective iodination of alkynes using a sulfonium iodate(I) electrophilc reagent under metal-free conditions has been realized. The reactivity of sulfonium iodate(I) salt could be significantly diverse in the presence of water as the solvent, enabling the (E)-1,2-diiodoalkenes stereospecifically. This stereodivergent approach is amenable to a wide range of alkyne substrates

  已经实现了在无金属条件下使用碘酸sulf（I）亲电试剂对炔烃进行高效且高度化学选择性的碘化反应。锍碘酸盐（的反应性我）盐可以是在水的存在下作为溶剂显著多样，使（ê）-1,2- diiodoalkenes立体专一性。这种立体发散方法适用于各种炔烃底物，并显示出不同的官能团耐受性，可合成有价值的1-碘炔烃和（E）-邻位二碘烯烃，收率良好至优异（高达99％），在100％的选择性下环境条件。
• Cobalt-catalyzed stereoselective iodosulfonylation and diiodination of alkynes via oxidation of potassium iodide in air
  作者：Nobukazu Taniguchi

  DOI：10.1016/j.tet.2018.02.004

  日期：2018.3

  Cobalt-catalyzed iodosulfonylation of alkynes can be achieved using sodium sulfinates in the presence of KI. This procedure produces numerous stereoselective (E)-β-iodoalkenyl sulfones with good yields and suppresses the formation of diiodoalkenes. Furthermore, when this reaction is performed in the absence of sodium sulfinates, the expected (E)-diiodoalkenes are obtained.

  在KI的存在下，使用亚磺酸钠可以实现炔烃的钴催化的碘磺酰化。该方法以良好的产率产生许多立体选择性的（E）-β-碘代烯基砜，并抑制了二碘代烯烃的形成。此外，当该反应在亚磺酸钠不存在下进行时，获得了预期的（E）-二碘代烯烃。
• An aqueous medium-controlled stereospecific oxidative iodination of alkynes: efficient access to (<i>E</i>)-diiodoalkene derivatives
  作者：Rammurthy Banothu、Swamy Peraka、Srujana Kodumuri、Durgaiah Chevella、Krishna Sai Gajula、Vasu Amrutham、Divya Rohini Yennamaneni、Narender Nama

  DOI：10.1039/c8nj03929a

  日期：——

  A new and versatile approach for the stereospecific iodination of alkynes has been developed in aqueous media. Scale-up reactions (up to 5 g) established the proficiency of this protocol and highlight the feasibility of large scale reactions.

  已在水性介质中开发了一种新的多功能方法，用于炔烃的立体特异性碘化反应。规模化反应（高达5克）证实了该方案的熟练性，并突显了大规模反应的可行性。
• Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2
  作者：Jing Xiao、Li-Biao Han

  DOI：10.1016/j.tet.2019.05.019

  日期：2019.6

  By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with

  通过使用I 2或I 2 / H 3 PO 3体系，将各种烯烃和炔烃以良好的产率转化为相应的烷基碘和烯基碘。在存在I 2的情况下，可以在室温下于空气中使用H 2 O作为溶剂将炔烃二碘化。由于可以通过萃取获得纯产物，因此该方法还具有简单的后处理程序。此外，首次将无毒廉价的膦酸H 3 PO 3与烯烃和炔烃成功加氢碘化，为有机碘的合成提供了一种简单实用的方法。
• A new and efficient method for the synthesis of α,α-dihaloketones by oxyhalogenation of alkynes using oxone®–KX (X = Cl, Br, or I)
  作者：Sridhar Madabhushi、Raveendra Jillella、Kishore Kumar Reddy Mallu、Kondal Reddy Godala、Venkata Sairam Vangipuram

  DOI：10.1016/j.tetlet.2013.05.072

  日期：2013.7

  A simple and efficient method for the preparation of α,α-dichloroketones, α,α-dibromoketones, and α,α-diiodoketones by oxyhalogenation of alkynes using oxone® and KX (X = Cl, Br, or I) is described.

  描述了一种通过使用oxone®和KX（X = Cl，Br或I）进行炔属化合物的卤代氧合制备α，α-二氯酮，α，α-二溴代酮和α，α-二碘代酮的简单有效的方法。