(S)-2-dibenzylamino-1-fluoropropane | 850374-28-6

• 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: (S)-2-dibenzylamino-1-fluoropropane
• 英文别名: (2S)-N,N-dibenzyl-1-fluoropropan-2-amine
• CAS: 850374-28-6
• 化学式: C₁₇H₂₀FN
• 分子量: 257.351
• InChiKey: TYAQDEZTQZEAFQ-HNNXBMFYSA-N

物化性质

• 沸点：
  333.2±22.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-dibenzylamino-1-fluoropropane 在 palladium on activated charcoal 作用下， 生成 (S)-(2-fluoro-1-methylethyl)amine
  参考文献：
  名称：

  Synthesis of (Fluoroalkyl)amines by Deoxyfluorination of Amino Alcohols

  摘要：

  氨基醇的去氧氟化是通过使用N,N-二乙基-α,α-二氟苯甲胺（DFBA）实现的，选择性地生成N-苯酰（氟烷基）胺。

  DOI：

  10.1055/s-2006-947316
• 作为产物：
  描述：

  (S)-(+)-2-(二苄氨基)-1-丙醇 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以74%的产率得到(S)-2-dibenzylamino-1-fluoropropane
  参考文献：
  名称：

  Nucleophilic fluorination of amino alcohols and diols using Deoxofluor

  摘要：

  Various fluorinated chiral compounds were synthesized using bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor) as a nucleophilic fluorinating reagent. Reactions of Deoxofluor (1) with amino alcohols (2a-d) and diols (2e-g) in methylene chloride at room temperature led to the formation of the corresponding fluoro derivatives (3a-g) in good yields.(C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00065-9

文献信息

• Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions
  作者：Yunwei Chen、Xiang Sun、Ningjie Wu、Jingbai Li、Shengnan Jin、Yongliang Zhong、Zirui Liu、Andrey Rogachev、Hyun-Soon Chong

  DOI：10.1039/c5ob01692d

  日期：——

  Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three-membered ring cogeners, aziridines and epoxides. The characterization of both optically active aziridinium ions and secondary β-halo amines as the

  iri啶鎓离子是用于合成对映体富集的结构单元的有用的反应性中间体。然而，与其他三元环同源热氮，氮丙啶和环氧化物相比，N，N-二烷基叠氮鎓离子在光学活性分子的合成中相对未被充分利用。几乎没有报道光学活性的叠氮鎓离子和仲β-卤代胺作为叠氮鎓离子的前体分子的表征，并且常常不清楚。在本文中，我们首次报道了旋光性叠氮鎓离子和仲β-卤代胺的制备以及实验和理论表征。旋光性次生N，NN，N-取代的丙氨醇通过卤化物在氮丙啶鎓离子的更受阻的碳上形成和开环而有效地合成了N-取代的β-卤代胺。通过NMR和计算分析对旋光性β-卤代胺和叠氮鎓离子进行了表征。通过X射线晶体学分析确认旋光性β-氯胺的结构。来自N，N的叠氮鎓离子-二苄基丙二醇仅在数小时内保持稳定，这对于分析NMR和光学活性而言足够长。使用DFT和高精度DLPNO-CCSD（T）方法，通过计算研究了卤化物对氮丙啶鎓离子的立体定向开环。氮丙啶鎓离子的高度区域
• Rearrangements accompanying fluorination of 2-amino alcohols and 1,2-diols with Deoxo-Fluor™
  作者：Chengfeng Ye、Jean’ne M. Shreeve

  DOI：10.1016/j.jfluchem.2004.06.013

  日期：2004.12

  2-Amino alcohols and 1,2-diols treated with Deoxo-Fluor™ in methylene chloride resulted in the formation of rearranged major products concomitantly with minor amounts of the straightforward fluorinated replacement products in good yields.

  用Deoxo-Fluor™在二氯甲烷中处理过的2-氨基醇和1,2-二醇导致重排的主要产物的形成，并伴有少量的简单氟化替代产物，收率很高。
• Process for Production of Optically Active Fluoroamine
  申请人：Ishii Akihiro

  公开号：US20110034732A1

  公开（公告）日：2011-02-10

  Disclosed is a process for producing a protected optically active fluoroamine, which comprises the step of reacting an imine-protected optically active hydroxyamine, an oxazolidine-protected optically active hydroxyamine, or a mixture of the imine-protected optically active hydroxyamine and the oxazolidine-protected optically active hydroxyamine, with sulfuryl fluoride (SO 2 F 2 ) in the presence of a tertiary amine having a carbon number of 7 to 18 (produced by substituting all of three hydrogen atoms in ammonia by alkyl groups). The desired optically active fluoroamine can be produced by hydrolyzing the protected optically active fluoroamine under acidic conditions.
• US8426645B2
  申请人：——

  公开号：US8426645B2

  公开（公告）日：2013-04-23
• Nucleophilic fluorination of amino alcohols and diols using Deoxofluor
  作者：Rajendra P. Singh、Jean’ne M. Shreeve

  DOI：10.1016/s0022-1139(02)00065-9

  日期：2002.7

  Various fluorinated chiral compounds were synthesized using bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor) as a nucleophilic fluorinating reagent. Reactions of Deoxofluor (1) with amino alcohols (2a-d) and diols (2e-g) in methylene chloride at room temperature led to the formation of the corresponding fluoro derivatives (3a-g) in good yields.(C) 2002 Elsevier Science B.V. All rights reserved.