(E)-(1-iodoethene-1,2-diyl)dibenzene | 119379-68-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-(1-iodoethene-1,2-diyl)dibenzene
• 英文别名: [(E)-1-iodo-2-phenylethenyl]benzene
• CAS: 119379-68-9
• 化学式: C₁₄H₁₁I
• 分子量: 306.146
• InChiKey: ARCBTFXUWARYBK-SDNWHVSQSA-N

物化性质

• 沸点：
  343.4±31.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-(1-iodoethene-1,2-diyl)dibenzene 在 silica gel 、 三碘化磷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (Z)-(1-iodoethene-1,2-diyl) dibenzene
  参考文献：
  名称：

  Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes

  摘要：

  The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a. On extended treatment (E)-4a underwent subsequent isomerization to the thermodynamically more stable Z isomer. Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions. In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution. In contrast with solution-phase hydriodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer. E reversible arrow Z equilibration of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides 13. Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation. Surface-mediated addition of Hbr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c. Treatment of the terminal alkynes 17 and 22 with (COBr)(2) over alumina gave the dibromides 20 and 24/25,respectively, whereas use of acetyl bromide as the Hbr precursor afforded the alkenyl bromides 18b and 23.

  DOI：

  10.1021/jo00090a031
• 作为产物：
  描述：

  二苯基乙炔 在 苯甲酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 18.33h， 生成 (E)-(1-iodoethene-1,2-diyl)dibenzene
  参考文献：
  名称：

  Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

  摘要：

  双键的光活化金属无氘化反应以环境友好的方式进行了开发。

  DOI：

  10.1039/d0gc03081c

文献信息

• A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles
  作者：Chengang Zhou、Dawei Ma

  DOI：10.1039/c3cc49724k

  日期：——

  CuI-catalyzed coupling of vinyl halides with carbazates gives N-protected N-alkenylhydrazines, which are condensed with ketones under acidic conditions to give polysubstituted pyrroles. The pyrrole synthesis may go through a similar mechanism with Fischer indole synthesis, which involves a [3,3]-sigmatropic rearrangement and other reactions.

  CuI催化的乙烯基卤化物与氨基甲酸酯的偶合生成N-保护的N-烯基肼，将其在酸性条件下与酮缩合，得到多取代的吡咯。吡咯合成可能会通过与Fischer吲哚合成相似的机理进行，其中涉及[3,3]-σ重排和其他反应。
• Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes
  作者：Albert M. DeBerardinis、Mark Turlington、Lin Pu

  DOI：10.1002/anie.201007351

  日期：2011.3.1

  tolerant: Vinylzinc reagents were directly prepared from the reaction of vinyl iodides with ZnEt2 under mild reaction conditions. The compound (S)‐1 was found to catalyze the addition of the vinylzinc reagents to a variety of aldehydes to generate structurally diverse allylic alcohols with high yields and enantioselectivities. This catalytic process can tolerate functional groups such as esters, chlorine

  温和且耐受：乙烯基碘试剂是由乙烯基碘化物与ZnEt 2在温和的反应条件下反应直接制备的。发现化合物（S）-1可以催化将乙烯基锌试剂添加到各种醛中，从而以高收率和对映选择性生成结构多样的烯丙基醇。该催化过程可以耐受底物上的官能团，例如酯，氯，醚和甲硅烷基醚。acac =乙酰丙酮酸酯，NMP = N-甲基-2-吡咯烷酮。
• Palladium‐Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand‐Assisted Halide Exchange
  作者：Philip Boehm、Tristano Martini、Yong Ho Lee、Bastien Cacherat、Bill Morandi

  DOI：10.1002/anie.202103269

  日期：2021.7.26

  broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds

  我们报道了一种高效且广泛适用的钯催化碘化方法，通过原位活化酰基氯并形成鏻盐，对廉价且丰富的芳基和乙烯基羧酸进行碘化。使用 1-碘丁烷作为碘化物源，与碱和脱氧氯化试剂结合使用，可以在 Pd/Xantphos 催化下获得各种芳基和乙烯基碘化物，包括复杂的药物样支架。化学计量实验和动力学分析表明了一种独特的机制，涉及 C−P 还原消除以形成 Xantphos 氯化鏻，随后通过外球亲核取代引发不寻常的卤素交换。
• Metal-Free Transfer Hydroiodination of C–C Multiple Bonds
  作者：Weiqiang Chen、Johannes C. L. Walker、Martin Oestreich

  DOI：10.1021/jacs.8b12318

  日期：2019.1.16

  The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Brønsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove

  描述了基于环己-1,4-二烯的气态碘化氢替代品的设计和克级合成。通过用中等强度的布朗斯台德酸引发，碘化氢从替代物转移到 CC 多重键上，例如炔烃和丙二烯，而没有游离碘化氢的参与。代用品碎片化为甲苯和乙烯，易挥发废物。这种氢碘化反应避免了对碘化氢或氢碘酸的不稳定处理。通过这种方式，可以以立体控制的方式访问范围广泛的以前未知或难以制备的乙烯基碘。
• Processes for the Preparation of Zuclomiphene and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20210147337A1

  公开（公告）日：2021-05-20

  The present invention provides processes for the preparation of zuclomiphene, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the carbometallation of diphenylacetylene with a compound of Formula (3) to afford either zuclomiphene or an intermediate which is converted to zuclomiphene.

  本发明提供了制备左环米非酮的方法，以及在制备过程中有用的中间体。具体来说，提供了一种用化合物（3）对二苯乙炔进行碳金属化反应的方法，从而得到左环米非酮或可转化为左环米非酮的中间体。