2,2,2-三氟-N-[2-[(2,2,2-三氟乙酰基)氨基]乙基]乙酰胺 | 360-43-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,2,2-三氟-N-[2-[(2,2,2-三氟乙酰基)氨基]乙基]乙酰胺
• 英文名称: N,N'-bis(trifluoroacetyl)ethylenediamine
• 英文别名: N,N'-bistrifluoroacetyl ethylenediamine；N,N'-ethylene-bis(trifluoroacetamide)；1,2-bis-(2,2,2-trifluoro-acetylamino)-ethane；1,2-Bis-(2,2,2-trifluor-acetylamino)-aethan；2,2,2-trifluoro-N-{2-[(trifluoroacetyl)amino]ethyl}acetamide；2,2,2-trifluoro-N-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]acetamide
• CAS: 360-43-0
• 化学式: C₆H₆F₆N₂O₂
• 分子量: 252.116
• InChiKey: BSMXDULOVFUYER-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  140 °C(Press: 0.001 Torr)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟-N-[2-[(2,2,2-三氟乙酰基)氨基]乙基]乙酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以95%的产率得到N,N'-Bis(2,2,2-trifluoroethyl)ethylenediamine
  参考文献：
  名称：

  N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction

  摘要：

  N,N-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide (8), synthesized by a simple four-step sequence from ethylenediamine and benzylidenetartaric acid, was designed in anticipation that the derived allylboronates 9-11 would display enhanced reactivity owing to the inductive effect of the N-trifluoroethyl substituents that would increase the Lewis acidity of the boron atom of the B-allyl-1,3,2-dioxaborolanes. Reagents 9-11 were synthesized by transesterification of 8 with the crystalline and easily purified allylboronate diethanolamine complexes 13, 19, and 25. Allylboronate 9 is ca. 100-fold more reactive than 6 and is also substantially more useful than the previously reported allyboronate 4, which suffers from very poor solubility in toluene at -78 degrees C. Most importantly, allylboronates 9-11 are significantly more enantioselective than the parent tartrate allylboronates 1-3 and rank among the most highly enantioselective allylboron reagents yet reported. Reactions of 9-11 with aldehydes are performed in THF at- -78 or -55 degrees C for 5-12 h periods. The enantioselectivity realized in reactions with achiral aldehydes is 92-95% ee (Table 2), and excellent diastereoselectivity is achieved in double asymmetric reactions with chiral aldehydes 15a, 15b, and 33 (Tables 3 and 4). For example, 16 and 28 are now available with a minimum selectivity of 92% from reactions of 15a and 15b with allylboronate 9, while the crotylboration products 29, 30, and 31 are available with a minimum selectivity of 90% (usually greater than or equal to 95%) from reactions of 15a and 15b with crotylboronates 10 and 11; the fourth isomer, 32a, is available with 83% selectivity. Chiral reagents 9-11 thus appear well suited for application to complex problems in organic synthesis.

  DOI：

  10.1021/jo00117a036
• 作为产物：
  描述：

  copper bis(ethyl-3-hydroxy-4,4,4-trifluoro-2-butenoate) 以 氯仿 为溶剂， 反应 24.0h， 以49%的产率得到2,2,2-三氟-N-[2-[(2,2,2-三氟乙酰基)氨基]乙基]乙酰胺
  参考文献：
  名称：

  Interaction of fluorine-containing 1,3-dicarbonyl compounds with polyamines

  摘要：

  In the reaction of fluorinated copper(II) 1,3-diketonates with diethylenetriamine (or triethylenetetramine) in CHCl3, N,N'-bis(1,3-aminovinylketones) are formed in 21-35% yields. Fluorine-containing 1,3-diketones and 1,3-ketoesters, upon interaction with polyamines without solvent, undergo acid cleavage, forming the corresponding amides. The copper(II) 1,3-ketoesterates are readily cleaved in CHCl3 at 25-degrees-C in excess triethylenetetramine or ethylenediamine.

  DOI：

  10.1007/bf00863371

文献信息

• Convenient One-Pot Synthesis of N-Substituted 3-Trifluoroacetyl Pyrroles
  作者：Nilo Zanatta、Ana Wouters、Leonardo Fantinel、Fabio da Silva、Rosemário Barichello、Pedro da Silva、Daniela Ramos、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-0028-1087821

  日期：——

  A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines, which generated 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same

  提出了一种新的一锅法合成一系列新的 N-取代 3-三氟乙酰基吡咯。这些化合物是通过 3-三氟乙酰基-4,5-二氢呋喃与伯胺反应得到的，反应生成 1,1,1-三氟-3-(2-羟乙基)-4-烷基氨基丁-3-en-2-one中间体。在大多数情况下，这些中间体不够稳定，无法分离。因此，在同一反应容器中，它们直接被 PCC（科里试剂）氧化以提供 1,1,1-三氟-3-(2-乙醛)-4-烷基氨基丁-3-en-2-ones，其中在回流下进行分子内环化，以中等产率得到所需的 N-取代 3-三氟乙酰基吡咯。
• THE REACTION OF ACETIC AND TRIFLUOROACETIC ANHYDRIDES WITH SOME SUBSTITUTED GUANIDINE HYDROCHLORIDES
  作者：W. F. Cockburn、R. A. B. Bannard

  DOI：10.1139/v57-171

  日期：1957.11.1

  Acetylation of the hydrochlorides of guanidine, cyclohexylguanidine, and 1-guanylpiperidine has been found to yield substituted triazines. Trifluoroacetylation of 1-guanylpiperidine hydrochloride also gives a triazine, whereas guanidine hydrochloride and cyclohexylguanidine hydrochloride are converted to bistrifluoroacetyl derivatives. The same triazines can also be obtained by acylation of the appropriate

  已经发现胍、环己基胍和1-胍基哌啶的盐酸盐的乙酰化产生取代的三嗪。1-胍基哌啶盐酸盐的三氟乙酰化也产生三嗪，而胍盐酸盐和环己基胍盐酸盐转化为双三氟乙酰基衍生物。同样的三嗪也可以通过适当的双胍酰化得到。
• Ethyl trifluoroacetate: a powerful reagent for differentiating amino groups
  作者：Daqiang Xu、Kapa Prasad、Oljan Repic、Thomas J. Blacklock

  DOI：10.1016/0040-4039(95)01655-4

  日期：1995.10

  Selective protection of primary amines in the presence of secondary amines and monofunctionalization of symmetric primary and secondary diamines using ethyl trifluoroacetate is described. Effective differentiation of primary, secondary and tertiary alkyl-substituted primary amines from one another by ethyl trifluoroacetate acylation is also demonstrated. These results are explained on the basis of

  描述了在仲胺存在下对伯胺的选择性保护以及使用三氟乙酸乙酯对对称伯和仲二胺进行单官能化。还证明了通过三氟乙酸乙酯酰化作用将伯，仲和叔烷基取代的伯胺彼此有效区分。这些结果是基于底物胺的空间和电子效应来解释的。
• 一种利用三氟乙酸乙酯制备高哌嗪的方法
  申请人：苏州百灵威超精细材料有限公司

  公开号：CN106699674B

  公开（公告）日：2019-06-18

  本发明公开了一种利用三氟乙酸乙酯制备高哌嗪的方法，其中，包括如下步骤：(1)以乙二胺为初始原料，在有机溶剂作用下，与三氟乙酸乙酯反应制得二三氟乙酰基乙二胺；(2)将步骤(1)中得到的二三氟乙酰基乙二胺，与1,3‑二取代丙烷化合物反应，在溶剂、催化剂的作用下，得到二三氟乙酰基高哌嗪；(3)将步骤(2)中得到的二三氟乙酰基高哌嗪，与氯化氢乙醇溶液反应得到高哌嗪二盐酸盐，并回收三氟乙酸乙酯；(4)将步骤(3)中得到的高哌嗪二盐酸盐，在溶剂、催化剂的作用下，与碱化反应制得高哌嗪。本发明具有以下有益效果：操作简便、成本较低、收率较高、污染较小、适用范围广，并且能满足产品工业化生产的需求。
• A facile access to new diazepines derivatives: Spectral characterization and crystal structures of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1 H -1,4-diazepine and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine
  作者：Guillermo Ahumada、David Carrillo、Carolina Manzur、Mauricio Fuentealba、Thierry Roisnel、Jean-René Hamon

  DOI：10.1016/j.molstruc.2016.07.047

  日期：2016.12

  and ethylenediamine. Compounds 1 – 3 were fully characterized by elemental analysis, FT-IR and multinuclear ( 1 H, 13 C and 19 F) NMR spectroscopy. In addition, their molecular identities and geometries have been authenticated by single-crystal X-ray diffraction analysis. The spectroscopic and structural data confirm that the 1,4-diazepine 2 and the 1,5-benzodiazepine 3 exist in the imine-enamine and

  摘要 2-苯甲酰基三氟丙酮 (2-TTA) 与乙二胺或邻苯二胺以 2:1 的化学计量摩尔比进行一锅双缩合反应，生成 7-(噻吩-2-基)-5- (trifluoromethyl)-2,3-dihydro-1 H -1,4-diazepine 2 和2-thiophene-4-trifluoromethyl-1,5-benzodiazepine 3 分别以56%和53%的产率分离出来。双(三氟乙酰胺)乙烯衍生物1也作为2-TTA和乙二胺反应的副产物以32％的产率分离。化合物 1-3 通过元素分析、FT-IR 和多核（ 1 H、 13 C 和 19 F）NMR 光谱进行了充分表征。此外，它们的分子特性和几何结构已通过单晶 X 射线衍射分析进行验证。光谱和结构数据证实 1,4-二氮卓 2 和 1,