(E)-1-methyl-4-(3,3,3-trifluoro-1-iodoprop-1-en-1-yl)benzene | 219517-83-6

• 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-methyl-4-(3,3,3-trifluoro-1-iodoprop-1-en-1-yl)benzene
• 英文别名: (E)-1-iodo-1-(p-methylphenyl)-3,3,3-trifluoropropene；(E)-1-iodo-1-p-tolyl-3,3,3-trifluoropropene；1-methyl-4-[(E)-3,3,3-trifluoro-1-iodoprop-1-enyl]benzene
• CAS: 219517-83-6
• 化学式: C₁₀H₈F₃I
• 分子量: 312.073
• InChiKey: NRKOBTZHZGBNKO-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丙炔-1-醇 、 (E)-1-methyl-4-(3,3,3-trifluoro-1-iodoprop-1-en-1-yl)benzene 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 反应 8.0h， 以52%的产率得到(E)-6,6,6-trifluoro-4-p-tolylhex-4-en-2-yl-1-ol
  参考文献：
  名称：

  Regio- and stereo-specific preparation of (E)-1-aryl-3,3,3-trifluoro-1-iodo-propenes and their palladium-catalyzed reaction with terminal alkynes

  摘要：

  A new type of iodo-containing trifluoromethylated building blocks were synthesized. The reaction of 1-aryl-3,3,3-trifluoropropynes 1 with lithium iodide in acetic acid at 75 degrees C gave (E)-1-aryl-3,3,3-trifluoro-1-iodo-propenes 2 in high yield, which undergo the palladium-catalyzed Sonogashira reaction with terminal alkynes afforded trifluoromethyl-containing 1,3-enynes in high yield. (c) 2008 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2008.01.002
• 作为产物：
  描述：

  1-甲基-4-(3,3,3-三氟丙-1-炔基)苯 在 lithium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以86%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：

  Regio- and stereo-specific preparation of (E)-1-aryl-3,3,3-trifluoro-1-iodo-propenes and their palladium-catalyzed reaction with terminal alkynes

  摘要：

  A new type of iodo-containing trifluoromethylated building blocks were synthesized. The reaction of 1-aryl-3,3,3-trifluoropropynes 1 with lithium iodide in acetic acid at 75 degrees C gave (E)-1-aryl-3,3,3-trifluoro-1-iodo-propenes 2 in high yield, which undergo the palladium-catalyzed Sonogashira reaction with terminal alkynes afforded trifluoromethyl-containing 1,3-enynes in high yield. (c) 2008 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2008.01.002

文献信息

• Iodotrifluoromethylation of Alkenes and Alkynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide
  作者：Zhaojia Hang、Zejiang Li、Zhong-Quan Liu

  DOI：10.1021/ol501380e

  日期：2014.7.18

  A scalable, selective, and operationally easy iodotrifluoromethylation of a wide range of alkenes and alkynes by using two simple and safe solids, sodium trifluoromethanesulfinate and iodine pentoxide, in aqueous medium has been developed. Mechanistic studies confirm that free-radical processes are involved in this system since the key radical intermediates such as CF3 and β-CF3 alkyl radicals have

  通过在水性介质中使用两种简单且安全的固体三氟甲烷亚磺酸钠和五氧化二碘，开发了可扩展，选择性且操作简便的各种烯烃和炔烃的碘三氟甲基化方法。机理的研究证实，因为键的自由基中间体如CF自由基方法涉及在该系统中3和β-CF 3个烷基具有通过旋捕获和电子自旋共振被清楚地检测到。
• Controlled Trifluoromethylation Reactions of Alkynes through Visible-Light Photoredox Catalysis
  作者：Naeem Iqbal、Jaehun Jung、Sehyun Park、Eun Jin Cho

  DOI：10.1002/anie.201308735

  日期：2014.1.7

  The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3‐containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF3I by environmentally benign and efficient visible‐light photoredox catalysis. Subtle differences in the combination

  在合成化学中，控制可形成多种产物的反应是一个极具吸引力和挑战性的概念。通过对环境无害且有效的可见光光氧化还原催化作用，从炔烃和CF 3 I选择性地生成了一组有价值的含CF 3分子，即三氟甲基化的烯基碘，烯烃和炔烃。催化剂，碱和溶剂的组合之间存在细微差异，因此可以控制炔烃与CF 3 I之间反应的反应性和选择性。
• A New and Improved Synthesis of <i>trans</i>-1,2-Diiodoalkenes and Their Stereospecific and Highly Regioselective Trifluoromethylation
  作者：Jianxin Duan、William R. Dolbier,、Qing-Yun Chen

  DOI：10.1021/jo9816663

  日期：1998.12.1

  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.