3-amino-2-benzylamino-1,1,1-trifluoropropane | 270253-11-7

• 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: 3-amino-2-benzylamino-1,1,1-trifluoropropane
• 英文别名: N²-benzyl-3,3,3-trifluoropropan-1,2-diamine；2-(N-benzylamino)-3,3,3-trifluoropropane-1-amine；(3-Amino-1,1,1-trifluoropropan-2-yl)(benzyl)amine；2-N-benzyl-3,3,3-trifluoropropane-1,2-diamine
• CAS: 270253-11-7
• 化学式: C₁₀H₁₃F₃N₂
• 分子量: 218.222
• InChiKey: ZVQBRWKRJPPJQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  合成左氧氟沙星 、 3-amino-2-benzylamino-1,1,1-trifluoropropane 以 甲苯 为溶剂， 反应 2.0h， 以81%的产率得到ethyl 1-(2-benzylamino-3,3,3-trifluoropropyl)-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  Novel 1-Trifluoromethyl Substituted 1,2-Ethylenediamines and Their use for the Synthesis of Fluoroquinolones

  摘要：

  A common approach to the synthesis of 1-trifluoromethyl-1,2-ethylenediamines was developed. Based on these original building blocks the new derivatives of N-substituted fluoroquinolones bearing the trifluoromethyl group were obtained. Through-space transmitted coupling constants (7)J(F-F) between the trifluoromethyl group and F-8 were measured in the F-19 NMR spectra of all fluoroquinolones examined and assigned unequivocally by using F-19{F-19} double resonance technique. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00107-1
• 作为产物：
  描述：

  Benzoylamino-3-nitro-1,1,1-trifluoropropane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3-amino-2-benzylamino-1,1,1-trifluoropropane
  参考文献：
  名称：

  Aizikovich; Korotaev, Russian Journal of Organic Chemistry, 1999, vol. 35, # 2, p. 207 - 208

  摘要：

  DOI：

文献信息

• 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。
• N-Substituted α-trifluoromethyl β-nitro amines in the synthesis of fluorine-containing 1,2-diamines, amino alcohols, and β-amino acids
  作者：V. Yu. Korotaev、A. Yu. Barkov、M. I. Kodess、I. B. Kutyashev、P. A. Slepukhin、A. Ya. Zapevalov

  DOI：10.1007/s11172-009-0257-2

  日期：2009.9

  Reactions of 2-diazo-1,1,1-trifluoro-3-nitropropane or 1-trifluoromethyl-2-nitroethenes with amines and amino alcohols afforded N-mono- and N,N-disubstituted α-trifluoromethyl β-nitro amines, which were used to obtain a number of trifluoromethyl-containing 1,2-diamines, amino alcohols, and β-amino acids.

  2-重氮-1,1,1-三氟-3-硝基丙烷或1-三氟甲基-2-硝基乙烯与胺和氨基醇反应生成N-单和N,N-二取代的α-三氟甲基β-硝基胺，用于获得许多含三氟甲基的 1,2-二胺、氨基醇和 β-氨基酸。
• Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions
  作者：Stefania Fioravanti、Alessia Pelagalli、Lucio Pellacani、Fabio Sciubba、Maria Cecilia Vergari

  DOI：10.1007/s00726-014-1749-4

  日期：2014.8

  Chiral (R)-1-phenylethylamine was successfully employed in a tandem aza-Henry addition-reduction reaction to give chiral beta-nitro alpha-trifluoromethyl amines. A subsequent coupling reaction with N-Boc-protected amino acids leads to obtain optically pure CF3-modified dipeptides carrying two different N-protecting groups. These peptidomimetic units are characterized by the presence of the [CH(CF3)NH] group as mimetic of the natural [CONH] peptidic bond and can be used for the synthesis of more complex CF3-modified peptides after selective deprotection of one of the two amine functions. 2D NMR spectral analyses were employed to determine the absolute configurations of all newly synthesized chiral compounds.