(S)-1-(4-fluorophenyl)but-3-en-1-amine | 949096-30-4

• 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)-1-(4-fluorophenyl)but-3-en-1-amine
• 英文别名: (1S)-1-(4-fluorophenyl)but-3-en-1-amine
• CAS: 949096-30-4
• 化学式: C₁₀H₁₂FN
• 分子量: 165.21
• InChiKey: NLXGUZPOWJQRTI-JTQLQIEISA-N

物化性质

• 沸点：
  221.9±28.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-fluorophenyl)but-3-en-1-amine 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 24.5h， 生成 (2S)-2-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  RETRACTED: Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

  摘要：

  An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.061
• 作为产物：
  描述：

  4-甲氧基-N-(4-氟亚苄基)苯胺 在 ammonium cerium (IV) nitrate 、 (R)-3,3'-二苯基-1,1'-联萘酚 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (S)-1-(4-fluorophenyl)but-3-en-1-amine
  参考文献：
  名称：

  手性联苯酚催化的不对称折叠硼-曼尼希烯丙基化反应

  摘要：

  手性联苯酚通过使用工作台稳定的烯丙基二氧硼杂硼烷催化醛和胺的不对称 Petasis 硼-曼尼希烯丙基化。该反应通过两步一锅法进行，需要 2-8 摩尔%的 3,3'-Ph 2 -BINOL 作为最佳催化剂。在微波加热下，该反应以优异的产率（高达 99%）和高对映选择性（高达 99:1）提供手性高烯丙胺。催化反应是真正的多组分缩合反应，而醛和胺都可以具有广泛的结构和电子特性。在反应中使用巴豆基二氧硼杂硼烷会产生具有反式和顺式非对映异构体的立体发散产物，其与相应的 E-和 Z-硼杂硼烷立体异构体均具有良好的非对映选择性和对映选择性。

  DOI：

  10.1002/anie.201611332

文献信息

• Synthesis of Enantiopure Benzyl Homoallylamines by Indium-Mediated Barbier-Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N-Containing Heterocycles
  作者：Ari Hietanen、Tiina Saloranta、Sara Rosenberg、Evelina Laitinen、Reko Leino、Liisa T. Kanerva

  DOI：10.1002/ejoc.200901216

  日期：2010.2

  N-(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding (S)-amines and (R)-amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide

  Barbier 型铟介导的不同 N,N-(二甲基氨磺酰基)-保护的醛亚胺与许多烯丙基溴的烯丙基化，然后进行高产率脱保护，以良好到极好的产率提供烯丙胺。然后对外消旋胺进行酶动力学拆分以获得相应的(S)-胺和(R)-酰胺。当具有末端双键的酰基供体应用于酶动力学拆分时，产物酰胺可以通过闭环复分解以直接的方式转化为不饱和内酰胺。此外，对映体纯的 (S)-1-苯基丁-3-烯胺被转化为相应的二烯丙胺，然后进行闭环复分解以产生模拟许多天然产物的取代脱氢哌啶。
• γ-Fluorophenyl-GABA derivatives from fluorobenzonitriles in high diastereomeric and enantiomeric excess
  作者：P. Veeraraghavan Ramachandran、G. Venkat Reddy、Debanjan Biswas

  DOI：10.1016/j.jfluchem.2008.10.002

  日期：2009.2

  An enantioselective synthesis of α-fluoroaryl homoallylic amines in 52–71% yields and 76–93% enantioselectivities has been achieved via the allylboration of the corresponding fluorinated N-aluminobenzaldimines with B-allyldiisopinocampheylborane in the presence of methanol, followed by alkaline hydrogen peroxide workup. Crotylboration of these aluminobenzaldimines with potassium B-methoxy B-E- or

  在甲醇存在下，通过将相应的氟化N-铝联苯二胺与B-烯丙基二ii基樟脑基硼烷进行烯丙基硼化，然后进行碱性过氧化氢处理，实现了α-氟芳基均烯丙基胺的对映选择性合成，产率为52-71％，对映选择性为76-93％。。这些aluminobenzaldimines与钾的Crotylboration乙-甲氧基乙- ë -或- Ž -crotyldiisopinocampheylborinate提供相应的β-抗或-顺式-甲基α-fluoroarylhomoallylamines，分别在高德和EE。同样，用锂B进行烷氧基烯丙基化-甲氧基B -γ-OMEMallyldiisopinocampheylborinate提供优秀的de和ee的相应的β-顺-烷氧基高烯丙基胺。通过氢硼化-氧化将这些氨基烯烃的代表转化为相应的具有光学活性的N -Boc保护的氟化氨基醇。进一步的铬介导的氧化提供了N -Boc保护的γ-氟苯
• Asymmetric Synthesis of δ-Substituted α,β-Unsaturated δ-Lactams by Ring Closing Metathesis of Enantiomerically Pure <i>N</i>-Acryloyl-homoallylic Amines
  作者：Claudio Fiorelli、Diego Savoia

  DOI：10.1021/jo0703000

  日期：2007.8.1

  Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl amides. Then, ring closing metathesis gave delta-substituted delta-lactams in good overall yields.
• Convenient Synthesis of Stable Aldimine−Borane Complexes, Chiral δ-Amino Alcohols, and γ-Substituted GABA Analogues from Nitriles
  作者：P. Veeraraghavan Ramachandran、Debanjan Biswas

  DOI：10.1021/ol0710919

  日期：2007.8.1

  A one-pot synthesis of stable aldimine-trialkylborane adducts, the first synthesis of C- and N-deuterated imine-borane complexes, and their application for a highly enantioselective (84-99% ee) synthesis of delta-amino alcohols and gamma-substituted gamma-aminobutyric acids, including deuterated amino acids from nitriles, are described.
• WO2023/76218
  申请人：——

  公开号：——

  公开（公告）日：——