(S)-1-phenyl-N-((furan-2-yl)methyl)ethanamine | 161170-64-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-phenyl-N-((furan-2-yl)methyl)ethanamine
• 英文别名: (S)-N-(furan-2-ylmethyl)-1-phenylethylamine；(1S)-N-(furan-2-ylmethyl)-1-phenylethanamine
• CAS: 161170-64-5
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: GWRYGVPRPBVFRS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-phenyl-N-((furan-2-yl)methyl)ethanamine 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (1S,5S,7R)-3-((S)-1-Phenyl-ethyl)-10-oxa-4-thia-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene 4,4-dioxide
  参考文献：
  名称：

  Preparation of enantiopure sultams by intramolecular Diels–Alder reaction of furan-containing vinylsulfonamides

  摘要：

  Enantiomerically pure delta- and gamma-sultams have been prepared by intramolecular [4+2] cycloaddition of N-1-phenylethyl substituted vinylsulforiamides with purely thermal activation and under high pressure, An optimized procedure for reductive debenzylation of the resultant delta-sultams is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00912-7
• 作为产物：
  描述：

  (S)-N-2-furylmethylidene-1-phenylethylamine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 50.25h， 以10.5 g的产率得到(S)-1-phenyl-N-((furan-2-yl)methyl)ethanamine
  参考文献：
  名称：

  用于对映选择性去质子化反应的新型潜在螯合手性氨基镁碱

  摘要：

  合成了一系列手性仲胺，结合了 5 或 6 元杂环，并用于制备新型手性镁双酰胺试剂。随后将这些酰胺碱应用于不对称去质子化反应中，以探索螯合辅助选择性增强的潜力。当使用噻吩衍生的镁双酰胺复合物时，可以在一系列前手性环己酮底物上实现良好的选择性（高达 87:13 er (R:S)）。

  DOI：

  10.1055/s-0030-1259282

文献信息

• Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes
  作者：Matt R. Adams、Chieh-Hung Tien、Robert McDonald、Alexander W. H. Speed

  DOI：10.1002/anie.201709926

  日期：2017.12.22

  first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three‐step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %)

  对映选择性亚胺氢硼化已证明了二氮杂膦烯作为手性催化剂的首次使用。已证明，由市售材料通过简单的三步合成方法制备的手性二氮杂ol烯具有最高的对映选择性，迄今为止，据报道该化合物与频哪醇硼烷一起对烷基亚胺进行硼氢化。在低（2 mol％）催化剂负载下，可获得高达88:12的对映体比例。显示了使用这种主要基团催化方案进行不对称还原的20个实例，包括药物对雷沙吉兰和芬迪林的合成。
• New Potentially Chelating Chiral Magnesium Amide Bases for Use in Enantioselective Deprotonation Reactions
  作者：William Kerr、Michael Middleditch、Allan Watson

  DOI：10.1055/s-0030-1259282

  日期：2011.1

  to prepare novel chiral magnesium bisamide reagents. These amide bases were subsequently applied within asymmetric deprotonation reactions to probe the potential for chelation-assisted selectivity enhancement. Good levels of selectivity could be achieved (up to 87:13 e.r. (R:S)) across a range of prochiral cyclohexanone substrates when employing a thiophene-derived magnesium bisamide complex.

  合成了一系列手性仲胺，结合了 5 或 6 元杂环，并用于制备新型手性镁双酰胺试剂。随后将这些酰胺碱应用于不对称去质子化反应中，以探索螯合辅助选择性增强的潜力。当使用噻吩衍生的镁双酰胺复合物时，可以在一系列前手性环己酮底物上实现良好的选择性（高达 87:13 er (R:S)）。
• Scope of the organocatalysed asymmetric reductive amination of ketones with trichlorosilane
  作者：François-Moana Gautier、Simon Jones、Xianfu Li、Stephen J. Martin

  DOI：10.1039/c1ob05965c

  日期：——

  A highly active organocatalyst has been shown to affect the asymmetric reductive amination of ketones producing both aromatic and aliphatic amines. At 1 mol% catalyst loading, a series of structurally diverse chiral amines were quickly and economically prepared with good enantioselectivity and generally useful yield. The efficient synthesis of the calcimimetic (+)-NPS R-568 (67%, 89% ee) demonstrated the synthetic applicability of this methodology.

  一个高度活性的有机催化剂已被证明能影响酮的不对称还原胺化，生成芳香胺和脂肪胺。在1摩尔%催化剂负载下，一系列结构多样的手性胺被迅速且经济地制备出来，具有良好的对映选择性和一般有用的产率。这种合成方法的有效性通过钙离子模拟剂(+)-NPS R-568（产率67%，对映体过量89%）的合成得到证明。
• Facile Synthesis of (<i>S,S</i>)‐1,2‐Diacylamides and (<i>S,S</i>)‐1,2‐Diamines with <i>C</i> ₂‐Symmetry
  作者：Lin Ai、Jichuan Xiao、Guo Wang、Xiumin Shen、Cong Zhang

  DOI：10.1080/00397910600770698

  日期：2006.9.1

  A series of chiral vicinal tertiary diacylamides with C-2-symmetry was synthesized from (S)-alpha-phenylethylamine, different aromatic aldehydes, and oxalyl chloride. The diacylamides obtained were then reduced to afford chiral vicinal diamines with C-2-symmetry. We propose that the diacylamides existed in four stable conformational isomers in solution because of the dihedral angle between acylamide bonds.
• Asymmetric synthesis of methyl N-(1-phenylethyl)-3-aza-10-oxatricyclo[5.2.1.01,5]-4-oxo dec-8-en-6-carboxylate by an intramolecular Diels-Alder reaction
  作者：J Zylber、A Tubul、P Brun

  DOI：10.1016/0957-4166(95)00018-k

  日期：1995.2

  The title compound can be obtained with up to five asymmetric centres of known absolute configuration by a diastereoselective intramolecular Diels-Alder reaction between optically active N-substituted furfurylamines and maleic anhydride, in which the chirality is transferred from one stereocentre to the four others.