(S)-3-benzylamino-4-phenyl-1-butene | 510728-30-0

• 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)-3-benzylamino-4-phenyl-1-butene
• 英文别名: (2S)-N-benzyl-1-phenylbut-3-en-2-amine
• CAS: 510728-30-0
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: XGOSYYRXBLQNOL-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-benzylamino-4-phenyl-1-butene 在 Grubbs catalyst first generation Oxone 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 74.0h， 生成 (1S,2S,5R,6R)-2,3,5-tribenzyl-7-oxa-3-azabicyclo[4.1.0]heptan-4-one
  参考文献：
  名称：

  Synthesis of Functionalized Piperidinones

  摘要：

  A versatile, stereoselective synthesis of 5-hydroxypiperidinones with substituents at N1, C3, and C6 has been developed. The sequence involves ring-closing metathesis of a diene amide and epoxidation of the resulting alkene, followed by.base-mediated elimination, and finally hydrogenation.

  DOI：

  10.1021/jo0267091
• 作为产物：
  描述：

  (S)-1-phenylbut-3-en-2-amine 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 (S)-3-benzylamino-4-phenyl-1-butene
  参考文献：
  名称：

  立体选择性铜催化分子内烯烃氨基氧化：底物和配体结构对选择性的影响

  摘要：

  报道了一种非对映选择性铜催化分子内烯烃氨基氧化的新方案，该方案从相应的 γ-烯基磺酰胺和 N-烯丙基脲中提供亚甲氧基官能化的二取代吡咯烷和五元环脲。此外，对映选择性去对称化反应也取得了一些成功。我们发现对映选择性和非对映选择性的水平可以通过选择铜 (II) 配体和底物 N 取代基来调节。

  DOI：

  10.1002/ejoc.201100444

文献信息

• Sequential Allylic Substitution/Pauson–Khand Reaction: A Strategy to Bicyclic Fused Cyclopentenones from MBH-Acetates of Acetylenic Aldehydes
  作者：Chada Raji Reddy、Paridala Kumaraswamy、Kiran K. Singarapu

  DOI：10.1021/jo500962d

  日期：2014.9.5

  approach for the construction of novel bicyclic fused cyclopentenones starting from Morita–Baylis–Hillman (MBH) acetates of acetylenic aldehydes with flexible scaffold diversity has been achieved using a two-step reaction sequence involving allylic substitution and the Pauson–Khand reaction. This strategy provided a facile access to various bicyclic cyclopentenones fused with either a carbocyclic or a

  使用包含烯丙基取代和Pauson-Khand反应的两步反应序列，已成功构建了一种新的双环稠合环戊烯酮（从具有柔性骨架多样性的炔属乙醛的Morita-Baylis-Hillman（MBH）乙酸酯开始）的构建方法。该策略提供了以良好收率容易地获得与碳环或杂环系统稠合的各种双环环戊烯酮的途径。
• A Highly Enantioselective Allylic Amination Reaction Using a Commercially Available Chiral Rhodium Catalyst: Resolution of Racemic Allylic Carbonates
  作者：Derek C. Vrieze、Garrett S. Hoge、Perrine Z. Hoerter、Jared T. Van Haitsma、Brian M. Samas

  DOI：10.1021/ol901031b

  日期：2009.7.16

  A novel method for the kinetic resolution of unsymmetrical acyclic allylic carbonates and the concurrent synthesis of enantioenriched secondary amines using a commercially available chiral catalyst is disclosed.

  公开了一种用于动力学拆分不对称无环烯丙基碳酸酯并使用可商购的手性催化剂同时合成对映体富集的仲胺的新方法。
• Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease
  作者：Shazia Zaman、Pietro Campaner、Andrew D. Abell

  DOI：10.1016/j.bmc.2006.09.009

  日期：2006.12

  A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition. (c) 2006 Elsevier Ltd. All rights reserved.
• Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity
  作者：Monissa C. Paderes、Sherry R. Chemler

  DOI：10.1002/ejoc.201100444

  日期：2011.7

  A new protocol for diastereoselective copper-catalyzed intra-molecular alkene aminooxygenation, which provides methyleneoxy-functionalized disubstituted pyrrolidines and five-membered cyclic ureas from the corresponding γ-alkenyl sulfonamides and N-allylureas, is reported. In addition, some success was achieved in enantioselective desymmetrizations reactions. We discovered that the level of enantioselectivity

  报道了一种非对映选择性铜催化分子内烯烃氨基氧化的新方案，该方案从相应的 γ-烯基磺酰胺和 N-烯丙基脲中提供亚甲氧基官能化的二取代吡咯烷和五元环脲。此外，对映选择性去对称化反应也取得了一些成功。我们发现对映选择性和非对映选择性的水平可以通过选择铜 (II) 配体和底物 N 取代基来调节。
• Synthesis of Functionalized Piperidinones
  作者：Mark E. Humphries、James Murphy、Andrew J. Phillips、Andrew D. Abell

  DOI：10.1021/jo0267091

  日期：2003.3.1

  A versatile, stereoselective synthesis of 5-hydroxypiperidinones with substituents at N1, C3, and C6 has been developed. The sequence involves ring-closing metathesis of a diene amide and epoxidation of the resulting alkene, followed by.base-mediated elimination, and finally hydrogenation.