(2Z,4E)-1,1,1-三氟-4-(甲基亚胺)-2-戊烯-2-醇 | 524939-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2Z,4E)-1,1,1-三氟-4-(甲基亚胺)-2-戊烯-2-醇
• 英文名称: 2-Penten-2-ol, 1,1,1-trifluoro-4-(methylimino)-
• 英文别名: 1,1,1-trifluoro-4-(methylamino)pent-3-en-2-one
• CAS: 524939-18-2
• 化学式: C₆H₈F₃NO
• 分子量: 167.131
• InChiKey: SNKFRXXAKXVABN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲基苯磺酰异氰酸酯 、 (2Z,4E)-1,1,1-三氟-4-(甲基亚胺)-2-戊烯-2-醇 以 氯仿 为溶剂， 反应 24.0h， 以88%的产率得到(Z)-1,1,1-trifluoro-3-tosylcarbamoyl-4-(4-methylamino)-4-methylbut-3-en-2-one
  参考文献：
  名称：

  β-氨基乙烯基三氟甲基酮与甲苯磺酸异氰酸酯的区域选择性反应

  摘要：

  甲苯磺酰基异氰酸酯与所述的NH-和α-CH-插入反应Ñ单取代的和Ñ，Ñ含三氟甲基-二取代的烯胺酮进行了研究。N-单取代的β-氨基乙烯基三氟甲基酮的N-甲苯磺酰基羰基化的区域选择性取决于烯胺酮的结构，反应温度，溶剂和催化剂的性质。通过X射线分析推导了氟化乙烯基磺酰脲3e的Z构型。N，N-二取代烯胺5a的反应用甲苯磺酰基异氰酸酯与α-CH-或COCF 3基团的氧原子发生亲电反应的产物混合物，即磺酰脲6a和甲苯磺酰胺7a的乙烯基。

  DOI：

  10.1016/s0040-4020(03)00106-6
• 作为产物：
  描述：

  三氟乙酰丙酮 、 甲胺 反应 24.0h， 以60%的产率得到(2Z,4E)-1,1,1-三氟-4-(甲基亚胺)-2-戊烯-2-醇
  参考文献：
  名称：

  Volatile asymmetric fluorinated (O^N)-chelated palladium complexes: From ligand sources to MOCVD application

  摘要：

  The work deals with the volatile asymmetric palladium complexes of beta-ketoiminate-type as a new direction to design the effective partially fluorinated ((ON)-N-boolean AND)-chelated precursors for metal-organic chemical vapor deposition (MOCVD). To determine the effect of the substituent on the donor nitrogen atom, [Pd(CF3COCHCN(R)CH3)(2)](2) complexes with R = CH3 (Mei-tfac) and N(CH3)(2) (dmht) were synthesized and characterized by elemental analysis, IR and NMR spectroscopy. The molecular and crystal structures of the complexes as well as the initial ligand sources HMei-tfac and Hdmht were determined by single-crystal XRD. The obtained a new crystallographic and thermal (TG/DTA) information combined with the crystal lattice energy calculations allowed to reveal the features of the N-substituted fluorinated complexes in comparison with their non-fluorinated analogs. The possibility of using the proposed compounds as MOCVD precursors was experimentally confirmed. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.07.039

文献信息

• aza-Annulation of β-aminovinyl trifluoromethyl ketones with acryloyl chloride: an efficient synthesis of 5-(trifluoroacetyl)-3,4-dihydro-2(1H)-pyridinones
  作者：Nataliya V. Lyutenko、Igor I. Gerus

  DOI：10.1016/j.tetlet.2013.05.108

  日期：2013.7

  The first example of aza-annulation of β-aminovinyl trifluoromethyl ketones with acryloyl chloride has been studied. 5-Trifluoroacetyl-containing 3,4-dihydro-2(1H)-pyridinones 3a–j were obtained from β-substituted enaminones 2a–j, whereas β-unsubstituted enaminone 4 gave a mixture of cyclic and acyclic products.

  已经研究了用丙烯酰氯对β-氨基乙烯基三氟甲基酮进行氮杂环化的第一个例子。含5-三氟乙酰基的3,4-二氢-2（1 H）-吡啶酮3a – j是从β-取代的烯胺酮2a – j获得的，而β–未取代的烯胺酮4得到了环状和无环产物的混合物。
• Regioselective reactions of β-aminovinyl trifluoromethyl ketones with tosyl isocyanate
  作者：Natalie V Lyutenko、Igor I Gerus、Alexey D Kacharov、Valery P Kukhar

  DOI：10.1016/s0040-4020(03)00106-6

  日期：2003.3

  The NH- and α-CH-insertion reactions of tosyl isocyanate with N-monosubstituted and N,N-disubstituted trifluoromethyl-containing enaminones have been studied. The regioselectivity of N-tosylcarbomoylation of N-monosubstituted β-aminovinyl trifluoromethyl ketones depends on the structure of enaminones, the reaction temperature, the nature of solvent and catalyst. The Z configuration of fluorinated vinylogous

  甲苯磺酰基异氰酸酯与所述的NH-和α-CH-插入反应Ñ单取代的和Ñ，Ñ含三氟甲基-二取代的烯胺酮进行了研究。N-单取代的β-氨基乙烯基三氟甲基酮的N-甲苯磺酰基羰基化的区域选择性取决于烯胺酮的结构，反应温度，溶剂和催化剂的性质。通过X射线分析推导了氟化乙烯基磺酰脲3e的Z构型。N，N-二取代烯胺5a的反应用甲苯磺酰基异氰酸酯与α-CH-或COCF 3基团的氧原子发生亲电反应的产物混合物，即磺酰脲6a和甲苯磺酰胺7a的乙烯基。
• Volatile asymmetric fluorinated (O^N)-chelated palladium complexes: From ligand sources to MOCVD application
  作者：N.S. Nikolaeva、N.V. Kuratieva、E.S. Vikulova、P.A. Stabnikov、N.B. Morozova

  DOI：10.1016/j.poly.2019.07.039

  日期：2019.10

  The work deals with the volatile asymmetric palladium complexes of beta-ketoiminate-type as a new direction to design the effective partially fluorinated ((ON)-N-boolean AND)-chelated precursors for metal-organic chemical vapor deposition (MOCVD). To determine the effect of the substituent on the donor nitrogen atom, [Pd(CF3COCHCN(R)CH3)(2)](2) complexes with R = CH3 (Mei-tfac) and N(CH3)(2) (dmht) were synthesized and characterized by elemental analysis, IR and NMR spectroscopy. The molecular and crystal structures of the complexes as well as the initial ligand sources HMei-tfac and Hdmht were determined by single-crystal XRD. The obtained a new crystallographic and thermal (TG/DTA) information combined with the crystal lattice energy calculations allowed to reveal the features of the N-substituted fluorinated complexes in comparison with their non-fluorinated analogs. The possibility of using the proposed compounds as MOCVD precursors was experimentally confirmed. (C) 2019 Elsevier Ltd. All rights reserved.