(S)-N-isopropyl-2-amino-2-phenyl-1-thiophenylethane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-N-isopropyl-2-amino-2-phenyl-1-thiophenylethane
• 英文别名: N-[(1S)-1-phenyl-2-phenylsulfanylethyl]propan-2-amine
• 化学式: C₁₇H₂₁NS
• 分子量: 271.426
• InChiKey: CPBNQSUCADFXQL-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  噁拉戈利杂质35 在 盐酸 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 苯 为溶剂， 反应 37.0h， 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
• 作为试剂：
  描述：

  正丁基锂 、 环己烷基甲醛 在 (S)-N-isopropyl-2-amino-2-phenyl-1-thiophenylethane 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 0.75h， 生成 (S)-1-cyclohexyl-1-pentanol 、 (R)-(+)-1-cyclohexylpentanol
  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

• Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes
  作者：Johan Granander、Richard Sott、Göran Hilmersson

  DOI：10.1016/s0957-4166(02)00864-9

  日期：2003.2

  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.