N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 | 500131-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺
• 英文名称: N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine
• 英文别名: N,N-diethyl-α,α-difluoro(meta-methylbenzyl)amine；N,N-Diethyl-alpha,alpha-difluoro-3-methylbenzylamine；N-[difluoro-(3-methylphenyl)methyl]-N-ethylethanamine
• CAS: 500131-50-0
• 化学式: C₁₂H₁₇F₂N
• 分子量: 213.27
• InChiKey: SGDDSVYULWVCQK-UHFFFAOYSA-N

物化性质

• 沸点：
  234℃
• 密度：
  1.030
• 闪点：
  96℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  D-吡喃木糖 、 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 在 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 作用下， 反应 12.0h， 以60%的产率得到2,3,4-tri-O-(m-methylbenzoyl)-β-D-xylopyranosyl fluoride
  参考文献：
  名称：

  Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine

  摘要：

  Deoxyfluorination of alcohols was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.089
• 作为产物：
  描述：

  避蚊胺 在 草酰氯 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以82%的产率得到N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺
  参考文献：
  名称：

  使用 α,α-二氟烷基胺轻松合成恶唑啉、噻唑啉和咪唑啉

  摘要：

  β-氨基醇、β-氨基硫醇和β-二胺可通过在温和条件下与α,α-二氟烷基胺反应分别转化为相应的恶唑啉、噻唑啉和咪唑啉衍生物。该反应适用于光学活性杂环化合物的合成。

  DOI：

  10.1055/s-2007-966038
• 作为试剂：
  描述：

  butyl 5-hydroxypentanoate 在 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 作用下， 以 正庚烷 为溶剂， 反应 0.17h， 以80%的产率得到butyl 5-fluoropentanoate
  参考文献：
  名称：

  Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine

  摘要：

  Deoxyfluorination of alcohols was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.089

文献信息

• Facile Synthesis of Bicyclo Orthoesters and Bicyclo Amide Acetals Using α,α-Difluoroalkylamines
  作者：Shoji Hara、Seiko Tange、Tsuyoshi Fukuhara

  DOI：10.1055/s-0028-1083145

  日期：——

  triols or diethanolamine using - difluoroalkylamines. The reaction proceeds under milder condi- tions compared with the conventional methods. 4-tert-Butyl-1-(4- ethynylphenyl)trioxabicyclo(2.2.2)octane, a new class of insecti- cide, was prepared from a triol in 3 steps using a difluoroalkyla- mine.

  双环原酸酯和酰胺缩醛由相应的三醇或二乙醇胺使用-二氟烷基胺制备。与传统方法相比，反应在更温和的条件下进行。4-叔丁基-1-(4-乙炔基苯基)三氧杂双环(2.2.2)辛烷是一类新的杀虫剂，由三元醇使用二氟烷基胺分三步制备而成。
• Selective mono-fluorination of diols via a cyclic acetal of N,N-diethyl-4-methoxybenzamide
  作者：Mitsuhiro Suwada、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1016/j.jfluchem.2007.04.020

  日期：2007.10

  Selective mono-fluorination of 1,2- and 1,3-diols was achieved using N,N-diethyl-4-methoxybenzamide diethyl acetal and Et3N-3HF. The reaction proceeds through a cyclic acetal of the benzamide, and only one hydroxy group was fluorinated and another one was acylated.

  使用N，N - N-二乙基-4-甲氧基苯甲酰胺二乙基乙缩醛和Et 3 N-3HF实现1,2-和1,3-二醇的选择性单氟化。反应通过苯甲酰胺的环状缩醛进行，仅一个羟基被氟化，另一羟基被酰化。
• Fluorine compound and fluorinating agent comprising the compound
  申请人：——

  公开号：US20040073065A1

  公开（公告）日：2004-04-15

  A fluorine compound represented by Formula (1) is provided. The above fluorine compound is effective for introducing a fluorine atom into a compound having an active group such as an oxygen-containing functional group, and it can be used for uses of surface treatment, cleaning and coating. Further, after the fluorination reaction, the above compound is recovered and can be reused as a starting material for producing the above fluorine compound, and it is useful for various fluorination processes. 1 (wherein X represents a nitrogen or phosphorus atom; R 0 , R 1 , and R 2 represent hydrogen, an alkyl group or aryl group which may have a substituent, and they each may be the same or different; and R 0 , R 1 , and R 2 may be combined with each other to form a ring).

  提供一种由式（1）表示的氟化合物。上述氟化合物对于将氟原子引入具有活性基团（如含氧功能基团）的化合物是有效的，可用于表面处理、清洁和涂覆等用途。此外，在氟化反应后，上述化合物可以回收并作为生产上述氟化合物的起始物质进行再利用，对于各种氟化过程是有用的。其中X代表氮或磷原子；R0、R1和R2代表氢、烷基或芳基，可能带有取代基，它们各自可以相同也可以不同；R0、R1和R2可以相互结合形成环。
• Selective monofluorination of diols using DFMBA
  作者：Atsushi Yoneda、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1039/b502471d

  日期：——

  Selective monofluorination of 1,2- and 1,3-diols was achieved by reaction with DFMBA. The method is applicable for the synthesis of optically-active fluorohydrin derivatives.

  通过与DFMBA反应实现1,2-和1,3-二醇的选择性单氟化。该方法适用于光学活性的氟代醇衍生物的合成。
• Intramolecular OH⋅⋅⋅Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif
  作者：Bruno Linclau、Florent Peron、Elena Bogdan、Neil Wells、Zhong Wang、Guillaume Compain、Clement Q. Fontenelle、Nicolas Galland、Jean-Yves Le Questel、Jérôme Graton

  DOI：10.1002/chem.201503253

  日期：2015.12.1

  is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogen‐bond (HB) properties of adjacent functional groups, as well as the HB‐accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH⋅⋅⋅F intramolecular HBs (IMHBs) has been established for conformationally restricted fluorohydrins, such interaction in

  氟化通常用于化合物性能优化。然而，氟化对相邻官能团氢键（HB）性质以及氟本身的HB接受能力的影响尚不完全清楚。尽管构象限制的氟代醇可以形成 OH⋅⋅⋅F 分子内 HBs (IMHBs)，但柔性化合物中的这种相互作用仍然存在疑问。与之前的报道相比，本文首次证明了无环饱和 γ-氟代醇中存在 OH⋅⋅⋅F IMHB，甚至对于母体 3-氟丙-1-醇也是如此。相对立体化学对相应的h1 J OH⋅⋅⋅F值具有至关重要的影响，如syn ‐ 和anti- 4-氟戊烷-2-ol (6.6 和 1.9 Hz) 所示。OH⋅⋅⋅F IMHBs 的大小及其对整体分子构象、氟化基序和烷基取代水平的强烈依赖性，通过量子化学计算得到了合理化。对于给定的烷基链，“屏蔽规则”适用于 OH⋅⋅⋅F IMHB 能量。令人惊讶的是，预测的 OH⋅⋅⋅F IMHB 能量仅比相应的 OH⋅⋅⋅OMe 弱一些。这些结果为脂肪醇氟化的影