(+)-(1R)-1-phenyl-2-(phenylthio)ethylamine | 197020-74-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine
• 英文别名: (S)-2-amino-2-phenyl-1-thiophenylethane；(1S)-1-phenyl-2-phenylsulfanylethanamine
• CAS: 197020-74-9
• 化学式: C₁₄H₁₅NS
• 分子量: 229.346
• InChiKey: QGJBHDAXCPCBDT-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine 在 sodium tetrahydroborate 作用下， 以 乙醇 、 苯 为溶剂， 反应 22.0h， 生成 (S)-N-isopropyl-2-amino-2-phenyl-1-thiophenylethane
  参考文献：
  名称：

  Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes

  摘要：

  Six chiral amino sulfides have been synthesised from the amino acids phenylalanine. phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with berizaldehyde. resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of > 98.5 and 95% respectively. These stereoselectivities were significantly, higher than those induced by the ether analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00864-9
• 作为产物：
  描述：

  (S)-N-t-Boc-2-amino-2-phenyl-1-thiophenylethane 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以63%的产率得到(+)-(1R)-1-phenyl-2-(phenylthio)ethylamine
  参考文献：
  名称：

  Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes

  摘要：

  Six chiral amino sulfides have been synthesised from the amino acids phenylalanine. phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with berizaldehyde. resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of > 98.5 and 95% respectively. These stereoselectivities were significantly, higher than those induced by the ether analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00864-9

文献信息

• A Simple Synthesis of β-Amino Sulfides
  作者：Hiroyuki Ishibashi、Masayuki Uegaki、Manami Sakai

  DOI：10.1055/s-1997-971

  日期：1997.8

  Thiols reacted with 2-oxazolidinones in the presence of alkoxides to give β-amino sulfides in high yields. The method was applied to the synthesis of 5,6-dihydro-1,4-thiazin-3(2H)-ones.

  硫醇在醇盐的存在下与2-噁唑烷酮反应，得到高产率的β-氨基硫醚。该方法被应用于合成5,6-二氢-1,4-噻嗪-3(2H)-酮。
• Configurational Flexibility of Epimeric β-Aminothioether-chelated Ruthenium(II) η⁶-Arene Complex Salts
  作者：Immo Weber、Frank W. Heinemann、Walter Bauer、Ulrich Zenneck

  DOI：10.1515/znb-2009-0117

  日期：2009.1.1

  so far. The relative diastereomer concentrations in solution depend mainly on the spatial requirements of the η6-arene ligand rather than on the thioether moiety. Diastereomer ratios and the absolute configurations in solution were studied by NMR and CD spectroscopy. The spectroscopic results fit to the absolute X-ray crystal structure parameters determined for the diastereomers present in the crystalline

  五种手性 β-氨基硫醚是通过基于文献方案的不同途径获得的。这些β-氨基硫醚中的三种与两种二-μ-氯-双氯[η6-芳烃]-钌(II)}衍生物反应，产生标题复合盐。复杂的阳离子表现出3个立体，即 钌和硫原子以及螯合配体骨架的手性苄基碳原子。钌和硫立体中心在平衡时差向异构化为四种 NMR 可区分的非对映异构体的混合物，但设计的手性苄基碳原子在迄今为止应用的所有条件下都是稳定的。溶液中的相对非对映体浓度主要取决于 η6-芳烃配体的空间要求，而不是硫醚部分。通过NMR和CD光谱研究了溶液中的非对映体比率和绝对构型。光谱结果符合为以结晶状态存在的非对映异构体确定的绝对 X 射线晶体结构参数。差向异构 β-氨基硫醚螯合钌 (II) η6-芳烃复合盐的图形摘要构型灵活性