4-fluoro-N,N-di(prop-2-ynyl)benzenamine | 1548800-78-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-fluoro-N,N-di(prop-2-ynyl)benzenamine
• CAS: 1548800-78-7
• 化学式: C₁₂H₁₀FN
• 分子量: 187.217
• InChiKey: LLTGGOVYDFUIJG-UHFFFAOYSA-N

物化性质

• 沸点：
  273.6±35.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-fluoro-N,N-di(prop-2-ynyl)benzenamine 在 氧气 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以78%的产率得到N-(4-fluorophenyl)-N-prop-2-ynylformamide
  参考文献：
  名称：

  Visible-light-induced oxidative formylation of N-alkyl-N-(prop-2-yn-1-yl)anilines with molecular oxygen in the absence of an external photosensitizer

  摘要：

  可见光诱导的氧化甲酰化反应，使用分子氧在温和的反应条件下，无需外部光敏剂，对N-烷基-N-(丙-2-炔-1-基)苯胺进行了研究。

  DOI：

  10.1039/c7cc03693k
• 作为产物：
  描述：

  3-溴丙炔 、 4-氟苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-fluoro-N,N-di(prop-2-ynyl)benzenamine
  参考文献：
  名称：

  Three-step pathway towards bis(1,2,3-triazolyl-γ-propylsilatranes) as Cu2+ fluorescent sensor, via ‘Click Silylation’

  摘要：

  A series of substituted aniline derivatized bis(1,2,3-triazolyl-gamma-propylsilatranes) 3a-3f were designed in good yield from their triethoxysilane analogues via Cu(I) 'Click Silylation'. All the silatranes 3a-3f were characterized by IR, NMR (H-1, C-13) and HRMS studies. All these compounds were explored for their thermal stability by thermogravimetric analysis (TGA)/differential thermal analysis (DTA)/differential scanning calorimetry (DSC) study and electronic properties by UV-vis spectroscopy and fluorescence study. The binding of silatranes 3a-3f to Cu2+ ion proves them to be good chemosensor. These silatranes were subjected to time dependent hydrolysis under normal atmospheric conditions. IR spectroscopic data support hydrolytic instability of 3a, 3c and 3e. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.043

文献信息

• Cobalt-Catalyzed Cyclization/Hydrosilylation Reaction of 1,6-Diynes Enabled by an Oxidative Cyclization–Hydrosilylation Mechanism
  作者：Jiaxing Dong、Xuebing Leng、Dongyang Wang、Liang Deng

  DOI：10.1021/acscatal.4c00473

  日期：2024.3.15

  preparation of five-membered ring-fused silyl dienes that are useful reagents in organic synthesis. Only a handful of noble metal catalysts facilitating this transformation are known, and nonprecious metal catalysts effecting the reaction have remained elusive. Herein, we report that low-coordinate Co(0)-N-heterocyclic carbene complexes can catalyze the cyclization/hydrosilylation of 1,6-diynes with tertiary

  过渡金属催化的 1,6-二炔环化/氢化硅烷化是制备五元环稠合甲硅烷基二烯的有用方法，五元环稠合甲硅烷基二烯是有机合成中有用的试剂。只有少数促进这种转化的贵金属催化剂是已知的，而影响该反应的非贵金属催化剂仍然难以捉摸。在此，我们报道低配位Co(0)-N-杂环卡宾配合物可以催化1,6-二炔与叔氢和仲氢硅烷的环化/氢化硅烷化，提供五元环稠合( Z )-1-甲硅烷基二烯具有良好的产率和优异的立体选择性。机理研究表明催化循环很可能以Co(0)物种的1,6-二炔氧化环化为关键步骤。该机制解释了钴催化环化/氢化硅烷化反应中的高立体选择性且不存在未环化的氢化硅烷化副产物，这与贵金属催化反应的氢化硅烷化-环化机理不同。
• Synthesis of polyfunctional triethoxysilanes by ‘click silylation’
  作者：Gurjaspreet Singh、Satinderpal Singh Mangat、Jandeep Singh、Aanchal Arora、Ramesh K. Sharma

  DOI：10.1016/j.tetlet.2013.12.037

  日期：2014.1

  The copper-catalyzed 'click silylation' has been exploited for the chemical modification of gamma-azidopropyltriethoxysilane (AzPTES) with a wide range of terminal alkynes (la-lv) in a one-pot operation. The novel 1,2,3-triazole-triethoxysilane derivatives (2a-2v) were synthesized by this procedure and comprehensively characterized by IR spectra, H-1 and C-13 NMR, and HRMS studies. (C) 2013 Elsevier Ltd. All rights reserved.
• Pyrrolylmethyl Functionalized <i>o</i>-Carborane Derivatives
  作者：Huimin Dai、Guifeng Liu、Xiaolei Zhang、Hong Yan、Changsheng Lu

  DOI：10.1021/acs.organomet.6b00082

  日期：2016.5.23

  The reactions of the 16e half-sandwich complex CpCoS2C2B10H10 (1), diazo esters, and various 1,6-diynes (3a-i; PhN(CH2C-CH)(2), 4-Me-PhN(CH2C=CH)(2), 4-O-Me-PhN(CH2C=CH)(2), 4-F-PhN(CH2C=CH)(2), BzN(CH2=CH)(2), O(CH2=CH)(2), C(Ac)(2)(CH2C=CH)(2), N(CH2C=CH),, CH)(3) NH(CH2C=CH)N(CH2C=CH)(2) were investigated, in which two novel types of B-H activated products CpCoS2B10H9(CH2CO2Et) C5H3N(R) ( CH= CHCO2Et) (4a-c; R = Ph, 4 -Me-Ph, 4-OMe-Ph) and the key intermediate CpCoS2B10H9(CHCO2Me) (CH2CO2Me) (9) were isolated. 9 features a reactive Co-B bond, which triggers insertion of various 1,6-diynes to further lead to different final products. Substrates 3a-c are activated by the Co-B bond to produce o-carborane derivatives 4a-c which are functionalized by a cobalt-complexed eta(3)-pyrrolylmethyl group. The pyrrole ring is formed by in situ ring closure of 1,6-diynes. Control experiments and isolation of the intermediate CpCoS2B10H9(CHCO2Me)(CH2CO2Me)HC=CCH2N(4-Me-Ph)(CH2C=CH) (10) support the proposed mechanism concerning the formation of 4a-c analogues by oxidation. All of the new complexes were characterized by NMR, IR, elemental analysis, and mass spectrometry. The structures of 4a-6a and 9 were determined by single-crystal X-ray diffraction analysis as well.