1,3,4,5,6,8-hexafluoro-2,7-diaminonaphthalene | 612825-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3,4,5,6,8-hexafluoro-2,7-diaminonaphthalene
• 英文别名: 1,3,4,5,6,8-hexafluoro-2,7-naphthylenediamine；hexafluoro-2,7-naphthylenediamine；2,7-diaminohexafluoronaphthalene；hexafluoropseudo-meta-naphthylenediamine；2,7-DAHFN；1,3,4,5,6,8-Hexafluoronaphthalene-2,7-diamine
• CAS: 612825-51-1
• 化学式: C₁₀H₄F₆N₂
• 分子量: 266.146
• InChiKey: TWBDMWYHIGVYKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,4,5,6,8-hexafluoro-2,7-diaminonaphthalene 、 甘油 在 三氟甲磺酸 、 硼酸 作用下， 反应 8.0h， 以40%的产率得到9-amino-5,6,7,8,10-pentafluorobenzo[f]quinoline
  参考文献：
  名称：

  Skraup-like cyclization of polyfluoro-2-naphthylamines: Vicarious electrophilic substitution of fluorine

  摘要：

  Treatment of polyfluoro-2-naphthylamines with glycerol in H2SO4 or CF3SO3H at 150-160 degrees C gives respective polyfluorobenzo[f]quinolines. The reaction is suggested to proceed via intramolecular vicarious electrophilic substitution of fluorine at the alpha-position of polyfluorinated naphthalene core. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.03.001
• 作为产物：
  描述：

  八氟萘 在 ammonium hydroxide 作用下， 反应 5.0h， 以61%的产率得到2-氨基七氟萘
  参考文献：
  名称：

  液氨中八氟萘的胺化：2,6-和2,7-二氨基六氟萘的选择性制备

  摘要：

  液氨对八氟萘进行单胺化反应主要得到2-氨基七氟萘（分离产率为85-90％）。八氟萘的氨基化或2-氨基七氟萘的氨基化可提供异构体1,6-，1,7-，2,6-和2,7-二氨基六氟萘的混合物，其中普遍存在2,7-异构体（约70％）因此，它是2-取代的聚氟萘在7位上主要取代的第一个例子。的2- 2,7 / 2,6比X -heptafluoronaphthalene（X  =  - NH，NH 2NHAc）的胺化随着取代基的供电子作用的降低而减少。2，7-二氨基六氟萘与2-氨基七氟萘或八氟萘与液态氨中过量的NaNH 2和2，6-二氨基六氟萘在2-乙酰基氨基七氟萘与液氨反应，然后乙酰酰胺基水解的反应中形成。阐述了基于氨基的可逆转化选择性制备这些二胺的方法，以及通过与冠醚络合而分离出高纯度的简便技术。

  DOI：

  10.1016/j.jfluchem.2007.11.010

文献信息

• Supramolecular 1D assemblies of polyfluorinated arylenediamines and 18-crown-6
  作者：S. Z. Kusov、Yu. V. Gatilov、I. Yu. Bagryanskaya、G. V. Romanenko、T. A. Vaganova、I. K. Shundrina、E. V. Malykhin

  DOI：10.1007/s11172-010-0090-7

  日期：2010.2

  Rods (1D assemblies) formed by alternate crown ether and arylenediamine molecules are the motif of the supramolecular architecture of crystals of molecular associates of 18-crown-6 with tetrafluoro-1,4- and -1,3-phenylenediamines, hexafluoro-2,6- and -2,7-naphthylenediamines. Molecules in the assemblies are arranged via H-bond predominantly between the crown ether oxygen atoms and the polyfluoroarene amino group hydrogen atoms. Influence of the amino groups mutual arrangement and the aromatic framework size on the crystal supramolecular architecture is characterized. Specific melting heats of the crystalline 1D assemblies of para- and pseudo-para-arylenediamines are higher than those of meta- and pseudo-meta-analogs; the associates having higher melting heats selectively crystallize from solutions of isomeric phenylene- or naphthylenediamine mixtures.

  18-冠醚和芳基二胺分子交替形成的棒状（一维组合体）是 18-冠醚-6与四氟-1,4-和-1,3-苯二胺、六氟-2,6-和-2,7-萘二胺分子化合物晶体超分子结构的主题。组装体中的分子主要通过冠醚氧原子和多氟烯烃氨基氢原子之间的氢键进行排列。氨基的相互排列和芳香族框架的大小对晶体超分子结构的影响是显而易见的。对位芳香族二胺和假对位芳香族二胺的结晶一维集合体的特定熔热高于元对位芳香族二胺和假元对位芳香族二胺的结晶一维集合体的特定熔热；具有较高熔热的同系物可选择性地从异构苯二胺或萘二胺混合物的溶液中结晶出来。
• Design of zigzag-like supramolecular 1D assemblies of polyfluorinated meta-arylenediamines and 18-crown-6
  作者：Tamara A. Vaganova、Soltan Z. Kusov、Inna K. Shundrina、Yurij V. Gatilov、Evgenij V. Malykhin

  DOI：10.1016/j.molstruc.2011.03.067

  日期：2011.5

  According to the X-ray crystal data, 1D assemblies formed by alternate arylenediamine and crown ether molecules are the motif of the supramolecular architecture of crystal associates of 18-crown-6 and polyfluorinated rneta-arylenediamines, i.e. 2,4,5-trifluoro-, tetrafluoro-, 2,5,6-trifluoro-4-trifluoromethyl-, 2,5-difluoro-4,6-bis(trifluoromethyl)-1,3-phenylenediamines, and hexafluoro-2,7-naphthylenediamine. Molecules in the assemblies are coordinated by means of the hydrogen bond between the oxygen atoms of the crown ether and the hydrogen atoms of the polyfluoroarene amino groups. Due to the mutual meta-location of amino groups in a rigid aromatic framework, the molecules of the each component are arranged in a zigzag line along the rod axis. The zigzag arrangement of components in the 1D assemblies and the supramolecular architecture of co-crystals persist when the aromatic framework size increases and when one or two bulky CF3 groups are incorporated into ortho-positions to the amino groups. Using differential scanning calorimetry (DSC), specific melting heats of co-crystals have been determined, which trend towards a decrease with an increase of the 1D assembly unit lengths. (C) 2011 Elsevier B.V. All rights reserved.
• Skraup-like cyclization of polyfluoro-2-naphthylamines: Vicarious electrophilic substitution of fluorine
  作者：Galina A. Selivanova、Alexey V. Reshetov、Irina Yu Bagryanskaya、Vitalij D. Shteingarts

  DOI：10.1016/j.jfluchem.2012.03.001

  日期：2012.5

  Treatment of polyfluoro-2-naphthylamines with glycerol in H2SO4 or CF3SO3H at 150-160 degrees C gives respective polyfluorobenzo[f]quinolines. The reaction is suggested to proceed via intramolecular vicarious electrophilic substitution of fluorine at the alpha-position of polyfluorinated naphthalene core. (c) 2012 Elsevier B.V. All rights reserved.
• Amination of octafluoronaphthalene in liquid ammonia
  作者：Tamara A. Vaganova、Soltan Z. Kusov、Vladimir I. Rodionov、Inna K. Shundrina、Georgij E. Sal’nikov、Victor I. Mamatyuk、Evgenij V. Malykhin

  DOI：10.1016/j.jfluchem.2007.11.010

  日期：2008.4

  (X = −NH, NH2 and NHAc) amination diminishes with the decrease of electron-donating effect of the substituent; 2,7-diaminohexafluoronaphthalene forms in the reactions of 2-aminoheptafluoronaphthalene or octafluoronaphthalene with excess of NaNH2 in liquid ammonia and 2,6-diaminohexafluoronaphthalene—in the reaction of 2-acetylamidoheptafluoronaphthalene with liquid ammonia followed by acetylamido group

  液氨对八氟萘进行单胺化反应主要得到2-氨基七氟萘（分离产率为85-90％）。八氟萘的氨基化或2-氨基七氟萘的氨基化可提供异构体1,6-，1,7-，2,6-和2,7-二氨基六氟萘的混合物，其中普遍存在2,7-异构体（约70％）因此，它是2-取代的聚氟萘在7位上主要取代的第一个例子。的2- 2,7 / 2,6比X -heptafluoronaphthalene（X  =  - NH，NH 2NHAc）的胺化随着取代基的供电子作用的降低而减少。2，7-二氨基六氟萘与2-氨基七氟萘或八氟萘与液态氨中过量的NaNH 2和2，6-二氨基六氟萘在2-乙酰基氨基七氟萘与液氨反应，然后乙酰酰胺基水解的反应中形成。阐述了基于氨基的可逆转化选择性制备这些二胺的方法，以及通过与冠醚络合而分离出高纯度的简便技术。