1-(3,3-difluoroprop-1-ynyl)-2-methoxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3,3-difluoroprop-1-ynyl)-2-methoxybenzene
• 英文别名: 1-(2-methoxyphenyl)-3,3-difluoropropyne；1-(2-Methoxyphenyl)-3,3-difluoro-1-propyne
• 化学式: C₁₀H₈F₂O
• 分子量: 182.17
• InChiKey: SMYKKUVBDJGECK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙炔基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 silver nitrate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 12.17h， 生成 1-(3,3-difluoroprop-1-ynyl)-2-methoxybenzene
  参考文献：
  名称：

  Oxidant- and Base-Free, Copper-Catalyzed Difluoromethylation of Haloalkynes

  摘要：

  DOI：

  10.1021/acs.orglett.3c03198

文献信息

• Difluoromethylation of Terminal Alkynes by Fluoroform
  作者：Satoshi Okusu、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/acs.orglett.5b01778

  日期：2015.8.7

  The difluoromethylation of terminal alkynes through the use of fluoroform as a source of difluorocarbene is described. The choice of solvents and bases was found to be crucial for the transformation. A series of terminal alkynes 1 were nicely converted into the corresponding difluoromethyl alkynes 2 using potassium tert-butoxide in n-decane in moderate to good yields. Functional groups such as methoxy

  描述了通过使用氟仿作为二氟卡宾的来源而使末端炔烃的二氟甲基化。发现溶剂和碱的选择对于转化至关重要。使用叔丁醇钾在正癸烷中的适当收率，将一系列末端炔烃1很好地转化为相应的二氟甲基炔烃2。在反应条件下，对甲氧基，二甲氨基和溴等官能团以及苯基，杂芳基和空间要求的萘基具有很好的耐受性。二氟甲基炔烃2一步转化为二氟甲基化的异恶唑3和1,2,3-三唑4 也实现了。
• Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
  作者：Tsutomu Konno、Jungha Chae、Masashi Kanda、Go Nagai、Kazushige Tamura、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1016/s0040-4020(03)01199-2

  日期：2003.9

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.