N-methyl-N-allyltrifluoroacetamide | 179404-69-4

• 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
• 英文名称: N-methyl-N-allyltrifluoroacetamide
• 英文别名: 2,2,2-trifluoro-N-methyl-N-2-propenylacetamide；2,2,2-Trifluoro-N-methyl-N-(prop-2-en-1-yl)acetamide；2,2,2-trifluoro-N-methyl-N-prop-2-enylacetamide
• CAS: 179404-69-4
• 化学式: C₆H₈F₃NO
• 分子量: 167.131
• InChiKey: MUGKBQBGCOPQKP-UHFFFAOYSA-N

物化性质

• 沸点：
  181.3±40.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-N-allyltrifluoroacetamide 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-甲基烯丙基胺
  参考文献：
  名称：

  Highly Enantioselective Intramolecular Cyclopropanation Reactions of N-Allylic-N-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates

  摘要：

  Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N-methyldiazoacetamide, catalysis by dirhodium(II) tetrakis[methyl 2-oxapyrrolidine-5(S)-carboxylate], Rh-2(5(S)-MEPY)(4), achieved the highest yield and enantioselectivity (93% eel. Dirhodium(II) tetrakis[methyl 2-oxo-1-(3-phenylpropanoyl)imidazolidin-4(S)-carboxylate] Rh-2(4S)-MPPIM)(4), was preferred for substituted N-allylic-N-methyldiazoacetamides from which 92-95% ee's were obtained in intramolecular cyclopropanation reactions (88-95% yields), even when the catalyst was employed in only 0.1 mol %, Competition with intramolecular dipolar cycloaddition was minimized with the use of N-methyldiazoacetamides relative to N-tert-butyldiazoacetamides.

  DOI：

  10.1021/jo9519219
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 三氟乙酸酐 在 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 以9.4 g (75%)的产率得到N-methyl-N-allyltrifluoroacetamide
  参考文献：
  名称：

  Substituted tetracyclic azepine derivatives

  摘要：

  这项发明涉及式(I)的化合物，其药学上可接受的盐和立体异构体，以及它们的N-氧化物形式。其中：R.sup.1和R.sup.2分别独立地是氢；C.sub.1-6烷基；C.sub.1-6烷基羰基；三卤甲基羰基；带有羟基、C.sub.1-6烷氧基、羧基、C.sub.1-6烷基羰氧基、C.sub.1-6烷氧羰基或芳基的C.sub.1-6烷基；或者R.sup.1和R.sup.2与它们所连接的氮原子一起可以形成吗啡啉环或一个可选择地取代的杂环；R.sup.3、R.sup.4、R.sup.5、R.sup.6、R.sup.9、R.sup.10、R.sup.11或R.sup.12分别独立地是氢、卤、氰、羟基、三氟甲基、三氟甲氧基、羧基、硝基、氨基、单或双(C.sub.1-6烷基)-氨基、C.sub.1-6烷基羰胺基、氨基磺酰基、单或双(C.sub.1-6烷基)-氨基磺酰基、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6烷基羰基、C.sub.1-6烷氧羰基；R.sup.7和R.sup.8各自独立地是氢、羟基、C.sub.1-6烷基、C.sub.1-6烷氧基或R.sup.7和R.sup.8一起可以形成单或双(氰)亚甲基，或者与它们连接的碳原子一起形成羰基或螺旋取代基；或者R.sup.7和R.sup.8一起可以形成亚甲基；R.sup.13是氢、C.sub.1-6烷基或三氟甲基；R.sup.14是氢、C.sub.1-6烷基、氰或三氟甲基；n为0到6。这些化合物在大鼠中作为mCPP拮抗剂进行了测试。式(I)的化合物可用作治疗或预防中枢神经系统疾病、心血管疾病或消化系统疾病的治疗剂。

  公开号：

  US05552399A1

文献信息

• Organic-Fluorous Phase Switches:  A Fluorous Amine Scavenger for Purification in Solution Phase Parallel Synthesis
  作者：Bruno Linclau、Ashvani K. Sing、Dennis P. Curran

  DOI：10.1021/jo9823442

  日期：1999.4.1

  The synthesis of the fluorous amine scavenger [(C(6)F(13)CH(2)CH(2))(3)SiCH(2)CH(2)CH(2)](2)NH and its successful application in the automated solution phase parallel synthesis of a urea library are described. Ureas were made by robotic synthesis from organic amines and excess isocyanates. The amine scavenger reacts with excess isocyanate, and the fluorous tag serves to solubilize the resulting adduct

  氟胺清除剂[（C（6）F（13）CH（2）CH（2））（3）SiCH（2）CH（2）CH（2）]（2）NH的合成及其成功应用在自动化溶液阶段中，描述了尿素库的平行合成。尿素由有机胺和过量的异氰酸酯通过机器人合成而制得。胺清除剂与过量的异氰酸酯反应，并且氟标签用于溶解氟相中所得的加合物，因此可以通过氟有机萃取将其除去。液-液萃取后，有机尿素产品以高收率和纯度分离。初步生物学评估表明，几种脲具有离子通道调节能力。与聚合物和离子猝灭方法相比，无论产物可溶于还是不溶于反应介质，氟猝灭均有效。
• Phosphine-catalyzed acyl-transfer of heteroaryl ketones for the construction of N-fused heterocycles
  作者：Yu Zhang、De-Rui Han、Dan Ye、Hong Lu、Hao Wei

  DOI：10.1016/j.cclet.2023.108529

  日期：2024.3

  An inexpensive phosphine catalyst was used effectively for a transition-metal-free acyl-transfer of N-containing heteroaryl ketones for the rapid synthesis of N-fused heterocycles. The key pre-aromatic spirocyclic intermediate initialized by the single electron transfer (SET) process of Togni's reagent II promoted by the tertiary phosphine resulted in an intriguing and alternative tactic for the cleavage

  一种廉价的膦催化剂可有效地用于含N的杂芳基酮的无过渡金属酰基转移，从而实现快速合成N-稠合杂环。由叔膦促进的 Togni 试剂 II 的单电子转移 (SET) 过程引发的关键前芳香螺环中间体产生了一种有趣的替代 C-C 键断裂策略。通过使用廉价的叔膦作为催化剂，这种含N的杂芳基酮的骨架重组方法可以简化复杂的组装N-稠合杂环，具有广泛的官能团耐受性。
• Synthesis and structure–activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: a novel series of 5-HT2A/2C receptor antagonists. Part 1
  作者：J.Ignacio Andrés、Jesús Alcázar、José M Alonso、Adolfo Dı́az、Javier Fernández、Pilar Gil、Laura Iturrino、Encarna Matesanz、Theo F Meert、Anton Megens、Victor K Sipido

  DOI：10.1016/s0960-894x(01)00721-1

  日期：2002.1

  The synthesis of a series of novel 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives as well as their 5-HT2A/2C and H-1 receptor binding affinities are described. The in vivo activity as potential anxiolytics of the svnthesised compounds was measured in a mCPP challenge test. One of the compounds, 2a, proved to be a potent 5-HT2A 2C c receptor antagonist showing as well oral activity and therefore could be considered as a potential anxiolytic/antidepressant agent. (C) 2002 Elsevier Science Ltd. All rights reserved.
• SUBSTITUTED TETRACYCLIC AZEPINE DERIVATIVES WHICH HAVE AFFINITY FOR 5-HT2 RECEPTORS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0789701B1

  公开（公告）日：2001-02-07
• US5552399A
  申请人：——

  公开号：US5552399A

  公开（公告）日：1996-09-03