N-(2,2,2-trifluoro-ethylidene)benzylamine | 244793-66-6

• 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-(2,2,2-trifluoro-ethylidene)benzylamine
• CAS: 244793-66-6
• 化学式: C₉H₈F₃N
• 分子量: 187.164
• InChiKey: SVXVQGHKZKUEIS-NTUHNPAUSA-N

物化性质

• 沸点：
  173.9±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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-(2,2,2-trifluoro-ethylidene)benzylamine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 三氯化铝 、 tert-butyldimethylsilyl triflate 、 硫酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3S)-1-Benzyl-2-trifluoromethyl-piperidin-3-ol
  参考文献：
  名称：

  酒类曼尼希反应。将三甲基甲硅烷氧基呋喃加到氟化的亚胺中

  摘要：

  三氟甲基醛亚胺与三甲基甲硅烷基氧基呋喃在路易斯酸存在下反应，以高收率提供丁烯内酯，总非对映体选择性（> 98％）。这些产品的配置是反的。可以将被2-三氟甲基乙基胺取代的丁内酯4a转化为反式α-三氟甲基哌啶衍生物。

  DOI：

  10.1016/j.tetlet.2004.05.003
• 作为产物：
  描述：

  1,1,1-trifluoro-2-ethoxypropane 、 苄胺 以 甲苯 为溶剂， 以64%的产率得到N-(2,2,2-trifluoro-ethylidene)benzylamine
  参考文献：
  名称：

  Rapid access to CF3-containing heterocycles

  摘要：

  The silyl-Prins and aza-silyl-Prins reactions have been employed for the preparation of 6-CF3-substituted dihydropyrans and 6-CF3-substituted tetrahydropyridines. The product heterocycles have been further elaborated to a number of products, including CF3-substituted pipecolates and hydroxylated pyrans and piperidines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.178

文献信息

• Barbier Conditions for Reformatsky and Alkylation Reactions on Trifluoromethyl Aldimines
  作者：Benoit Crousse、Mickael Dos Santos、Danièle Bonnet-Delpon

  DOI：10.1055/s-2007-1000864

  日期：2008.2

  β-Trifluoromethyl β-amino acids and α-trifluoromethyl α-alkyl amines can be easily prepared under Barbier conditions from trifluoromethyl aldimines in moderate to good yields. β-Tri­fluoromethyl β-amino acids were obtained in good enantioselectivity from the chiral trifluoromethyl aldimine starting material.

  在Barbier条件下，可以通过中等至良好的产率轻松制备β-三氟甲基β-氨基酸和α-三氟甲基α-烷基胺。从手性三氟甲基亚胺前体出发，可以高对映选择性地获得β-三氟甲基β-氨基酸。
• Study of the Effect of Fluorine Atom(s) on Fluoromethylated Imines in the Tandem Mannich-Michael-type Reaction
  作者：Kouichi Murata、Tomoya Kitazume

  DOI：10.1002/ijch.199900021

  日期：——

  Differences in chemical behavior between non-fluorinated and fluorinated methylimines in the tandem Mannich–Michael-type reaction are described based on NMR and computational studies.

  基于NMR和计算研究描述了串联Mannich-Michael型反应中非氟化亚甲基亚胺和氟化亚甲基亚胺之间的化学行为差异。
• Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines
  作者：Laura Carroccia、Stefania Fioravanti、Lucio Pellacani、Claudia Sadun、Paolo A. Tardella

  DOI：10.1016/j.tet.2011.05.097

  日期：2011.7

  to be transformed into the corresponding diaziridines by a direct amination reaction with nosyloxycarbamates. The diastereoselective induction was strongly controlled by the N-substituent. Similar results were obtained in the epoxidation reactions performed on the same substrates using m-CPBA as oxidant. Starting from enantiopure imines chiral diaziridines or oxaziridines were obtained with very high

  （E）-三氟甲基亚胺被认为是理想的底物，可通过与壬基氧基氨基甲酸酯的直接胺化反应转化成相应的二氮丙啶。非对映选择性诱导受到N-取代基的强烈控制。使用m -CPBA作为氧化剂，在相同的底物上进行的环氧化反应获得了相似的结果。从对映体纯亚胺开始，以非常高的对映体纯度获得手性二氮丙啶或恶唑烷。
• Fluorinated β-nitro amines by a selective ZrCl4-catalyzed aza-Henry reaction of (E)-trifluoromethyl aldimines
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1039/c2ob26397a

  日期：——

  ZrCl4 was found to be an ideal catalyst to promote aza-Henry reactions between trifluoromethyl aldimines and some nitro alkanes giving new fluorinated β-nitro amines. The reaction is strongly influenced by the CF3 group, the yield by the alkyl chain of the nitro compound, while the stereochemical outcome seems to be unaffected, the anti isomer being always the major product.

  研究发现，ZrCl4 是一种理想的催化剂，可促进三氟甲基醛与某些硝基烷烃之间的偶氮-亨利反应，生成新的氟化δ-硝基胺。反应受 CF3 基团和硝基化合物烷基链的影响很大，而立体化学结果似乎不受影响，反异构体始终是主要产物。
• Solvent-Free Stereoselective Synthesis of (E)-Trifluoromethyl Imines and Hydrazones
  作者：Stefania Fioravanti、Lucio Pellacani、Paolo Tardella、Laura Carroccia

  DOI：10.1055/s-0030-1258280

  日期：2010.12

  ketimines, aldimines, and hydrazones starting from the corresponding trifluoromethyl carbonyl compounds or their hemiacetals is reported. The condensation reactions were performed under solvent-free conditions with a range of amines or hydrazines and proceeded with high stereoselectivity, always giving only the E-isomer in very good yields. fluorinated compounds - imines - hydrazones - stereo­selectivity

  据报道，从相应的三氟甲基羰基化合物或其半缩醛开始合成三氟甲基酮亚胺，醛亚胺和的新的，绿色的和有效的策略。缩合反应在无溶剂条件下与一系列胺或肼进行，并以高立体选择性进行，始终仅以非常好的收率得到E-异构体。 氟化化合物-亚胺--立体选择性-缩合