N-(4-methylphenyl)-1-(2,3,4,5,6-pentafluorophenyl)methanimine | 78161-64-5

• 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: N-(4-methylphenyl)-1-(2,3,4,5,6-pentafluorophenyl)methanimine
• CAS: 78161-64-5
• 化学式: C₁₄H₈F₅N
• 分子量: 285.216
• InChiKey: UEYPTOQSTVXTFQ-CGOBSMCZSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  318.7±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(4-methylphenyl)-1-(2,3,4,5,6-pentafluorophenyl)methanimine 在 sodium tetrahydroborate 、 copper(l) chloride 作用下， 生成 N-(2,3,4,5,6-pentafluorobenzyl) N-(2-cyanoethyl)-4-methylaniline
  参考文献：
  名称：

  维尔斯迈尔反应的观察第2部分--苄基-氰基乙基-4-甲基苯胺衍生物的反常反应

  摘要：

  研究了一系列标题苯胺（1）在Vilsmeier条件下与各种取代的苄基的反应。仅全氟苄基衍生物显示出正常的甲酰化，而其他氟衍生物给出了混合的结果，其他取代基仅给出了异常胺（5）和衍生自苄基的醛（6）。

  DOI：

  10.1016/s0040-4020(01)89174-2
• 作为产物：
  描述：

  五氟苯甲醛 、 乙烷,三氯氟- 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到N-(4-methylphenyl)-1-(2,3,4,5,6-pentafluorophenyl)methanimine
  参考文献：
  名称：

  p-Methyl-N-(pentafluorobenzylidene)aniline (1), 1,2,3,4-tetrafluoro-7-methoxyacridine (2), 1,2,3,4,7-pentafluoroacridine (3) and 3-(p-methylanilino)-1,2,4-trifluoro-7-methylacridine (4): four molecules representing key stages inthe one-pot synthesis of 1,2,3,4-tetrafluoroacridines by treating pentafluorobenzaldehyde with para-substituted anilines

  摘要：

  All of the title compounds, C14H8F5N, C14H7F4NO, C13H4F5N and C21H15F3N2, display a Characteristic stacking of their pi systems in which adjacent members of the stack are related by crystallographic inversion centres. This leads to a particularly efficient mode of packing in which fluorinated rings overlap unfluorinated sections of the molecules at interplanar spacings ranging from 3.40 to 3.51 angstrom.

  DOI：

  10.1107/s010827019400003x

文献信息

• A new one-pot synthesis of 1,2,3,4-tetrafluoroacridines and some 7-substituted derivatives [1]
  作者：Adrian J. Adamson、Ronald E. Banks、Anthony E. Tipping

  DOI：10.1016/s0022-1139(00)80058-5

  日期：1993.9

  1,2,3,4-Tetrafluoroacridine (1a) and a range of 7-substituted analogues can be synthesisedby heating pre-formed Schiff bases (E)-C6F5CH  NC6H4R-p (3) (fromC6F5CHO+H2NC6H4R-p) with the parent aniline H2NC6H4R-p (1:1 molar ratio) or byheating a mixture of the aldehyde C6F5CHO and the aniline H2NC6H4R-p (R  H, OMe,Me But, F, Cl and Br) (1:2 molar ratio) in toluene or 1,2-dichlorobenzene under reflux

  1,2,3,4-四氟ac啶（1a）和一系列7-取代的类似物可以通过加热预先形成的席夫碱（E）-C 6 F 5 CHNC 6 H 4 R- p（3）（由C 6 F 5 CHO + H 2 NC 6 H 4 R- p）与母体苯胺H 2 NC 6 H 4 R- p（1：1摩尔比）或通过加热醛C 6 F 5 CHO和乙醛的混合物苯胺H 2 NC甲苯或1,2-二氯苯中的6 H 4 R- p（RH，OMe，Me Bu t，F，Cl和Br）（摩尔比为1：2）。的某些反应的邻-取代的席夫碱2-（p -RC 6 H ^ 4 NH）C 6 ˚F 4 CHNC 6 H ^ 4 R- p（6）（RCl或Br），其催化onacid（由p - RC 6 H ^ 4 NH 3 + ˚F -）进行闭环反应，消除了苯胺p -RC 6 H 4 NH 2。除了RF，Cl或Br外，还形成大量相应的3-苯胺基-1,2,4
• Adamson, Adrian J.; Banks, R. Eric; Fields, Roy, Journal of Chemical Research, Miniprint, 1997, # 3, p. 530 - 555
  作者：Adamson, Adrian J.、Banks, R. Eric、Fields, Roy、Tipping, Anthony E.

  DOI：——

  日期：——
• p-Methyl-N-(pentafluorobenzylidene)aniline (1), 1,2,3,4-tetrafluoro-7-methoxyacridine (2), 1,2,3,4,7-pentafluoroacridine (3) and 3-(p-methylanilino)-1,2,4-trifluoro-7-methylacridine (4): four molecules representing key stages inthe one-pot synthesis of 1,2,3,4-tetrafluoroacridines by treating pentafluorobenzaldehyde with para-substituted anilines
  作者：A. J. Adamson、Y. Archambeau、R. E. Banks、B. Beagley、M. Helliwell、R. G. Pritchard、A. E. Tipping

  DOI：10.1107/s010827019400003x

  日期：1994.6.15

  All of the title compounds, C14H8F5N, C14H7F4NO, C13H4F5N and C21H15F3N2, display a Characteristic stacking of their pi systems in which adjacent members of the stack are related by crystallographic inversion centres. This leads to a particularly efficient mode of packing in which fluorinated rings overlap unfluorinated sections of the molecules at interplanar spacings ranging from 3.40 to 3.51 angstrom.
• KOZLOV N. S.; GLADCHENKO L. F.; KOROTYSHOVA G. P., VESTS. AN BSSR. CEP. XIM. N., IZV. AN BSSR. CEP. XIM. N., 1981, HO 1, 86-+
  作者：KOZLOV N. S.、 GLADCHENKO L. F.、 KOROTYSHOVA G. P.

  DOI：——

  日期：——
• Observations on the vilsmeier reaction Part 2. The anomalaus reaction of N-benzyl N-cyanoethyl-4-methylaniline derivatives
  作者：Andrew P. Shawcross、Stephen P. Stanforth

  DOI：10.1016/s0040-4020(01)89174-2

  日期：——

  The reaction of a series of the title anilines (1) with variously substituted benzyl groups under Vilsmeier conditions was investigated. Only perfluorobenzyl derivatives showed normal formylation while other fluoro derivatives gave mixed results and other substituents gave solely the anomalous amine (5) together with the aldehyde (6) derived from the benzyl group.

  研究了一系列标题苯胺（1）在Vilsmeier条件下与各种取代的苄基的反应。仅全氟苄基衍生物显示出正常的甲酰化，而其他氟衍生物给出了混合的结果，其他取代基仅给出了异常胺（5）和衍生自苄基的醛（6）。