1-(1-iodovinyl)-4-(trifluoromethyl)benzene | 359887-55-1

• 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: 1-(1-iodovinyl)-4-(trifluoromethyl)benzene
• 英文别名: 1-(1-iodoethenyl)-4-(trifluoromethyl)benzene
• CAS: 359887-55-1
• 化学式: C₉H₆F₃I
• 分子量: 298.046
• InChiKey: ZMASOPYPYFVUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 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：
  3

反应信息

• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 在 水 、 碘 、 三苯基膦 作用下， 以 氘代氯仿 为溶剂， 反应 48.0h， 以71%的产率得到1-(1-iodovinyl)-4-(trifluoromethyl)benzene
  参考文献：
  名称：

  使用I 2 / PPh 3 / H 2 O进行炔烃的便捷加氢碘化及其在Pd催化的交叉偶联反应中通过碘代烯烃一锅法合成三取代烯烃的应用

  摘要：

  已经开发出使用容易获得的诸如I 2，PPh 3和H 2 O的试剂对炔烃进行加氢碘化的方法。这扩展到使用Pd催化的交叉偶联和相关方法（例如Suzuki-Miyaura交叉偶联，Sonogashira交叉偶联反应和Mizoroki-Heck反应）通过碘代烯烃从炔烃一锅合成三取代烯烃。

  DOI：

  10.1016/j.tetlet.2014.10.039

文献信息

• 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 convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes
  作者：Giuseppe Bartoli、Roberto Cipolletti、Giustino Di Antonio、Riccardo Giovannini、Silvia Lanari、Mauro Marcolini、Enrico Marcantoni

  DOI：10.1039/c005042c

  日期：——

  The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl3 promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl3·7H2O–NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon–carbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid 1, named (R)-Tiagabine, which is a potent and selective γ-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans.

  不饱和体系在天然产物中的出现，以及CeCl3促进的方法所具有的温和性和广泛的适用性，提示在生物活性分子的全合成领域存在多个潜在的未来合成应用。在这个概念下，使用 ·7H2O–NaI体系作为有效的异相促进剂，在碳-碳三重键的碘功能化中得到了强调。研究表明，这种方法对于立体选择性合成三取代的（Z）或（E）碘烯特别有趣，只需改变溶剂的性质。该方法已成功应用于合成（R）-1-[4,4-双-(3-甲基-2-噻吩基)-3-丁烯基]-3-哌啶甲酸1，即（R）-Tiagabine，这是一种有效且选择性的γ-氨基丁酸（GABA）摄取抑制剂，在人类中具有经过验证的抗癫痫疗效。
• Ruthenium-Catalyzed Regioselective Hydrohalogenation of Alkynes Mediated by Trimethylsilyl Triflate
  作者：Yuye Bai、Zhenyuan Lin、Zhenying Ye、Dian Dong、Jing Wang、Lu Chen、Feng Xie、Yibiao Li、Pierre H. Dixneuf、Min Zhang

  DOI：10.1021/acs.orglett.2c03158

  日期：2022.11.4

  Here we describe a ruthenium-catalyzed regioselective hydrohalogenation reaction of alkynes under mild conditions. Commercially simple halogen sources such as KI, ZnBr2, and ZnCl2 were employed to achieve this transformation. Alkynes derived from bioactive molecules such as l-(−)-borneol, l-menthol, and estrone were also suitable for the transformation, demonstrating the potential synthetic value of

  在这里，我们描述了在温和条件下钌催化的炔烃区域选择性卤化氢反应。采用商业上简单的卤素源，如 KI、ZnBr 2和 ZnCl 2来实现这种转变。来自l -(-)-冰片、l-薄荷醇和雌酮等生物活性分子的炔烃也适用于转化，证明了这种新反应在有机合成中的潜在合成价值。
• Highly regioselective hydroiodination of terminal alkynes and silylalkynes with iodine and phosphorus reagents leading to internal iodoalkenes
  作者：Shin-ichi Kawaguchi、Haruna Masuno、Motohiro Sonoda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1016/j.tet.2012.08.096

  日期：2012.11

  Markovnikov-type hydroiodination of terminal alkynes with iodine and Ph2P(O)H took place selectively to afford the corresponding internal iodoalkenes in good yields. Combination of (PhO)(2)P(O)H and Ph2P(O)OH instead of Ph2P(O)H also provided internal iodoalkenes in excellent yields. This hydroiodination is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups. In addition, direct synthesis of internal iodoalkenes from silylalkynes was also achieved by using a mixed system of iodine and phosphorus reagents. (c) 2012 Elsevier Ltd. All rights reserved.
• Highly Selective Hydroiodation of Alkynes Using an Iodine−Hydrophosphine Binary System
  作者：Shin-ichi Kawaguchi、Akiya Ogawa

  DOI：10.1021/ol1005246

  日期：2010.5.7

  A novel hydroiodation of alkynes (1) using an iodine/hydrophosphine binary system takes place regioselectively to provide the corresponding Markovnikov-type adducts (2) in good yield. This hydroiodation is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups.