(S)-2-amino-3-phenyl-1-thioethylpropane | 340161-32-2

• 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)-2-amino-3-phenyl-1-thioethylpropane
• 英文别名: (S)-2-amino-1-(ethylsulfanyl)-3-phenylpropane；(2S)-1-ethylsulfanyl-3-phenylpropan-2-amine
• CAS: 340161-32-2
• 化学式: C₁₁H₁₇NS
• 分子量: 195.329
• InChiKey: RSUZOPHRFYXJKQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (S)-2-amino-3-phenyl-1-thioethylpropane 在 sodium tetrahydroborate 作用下， 以 乙醇 、 苯 为溶剂， 反应 22.0h， 生成 (S)-N-isopropyl-2-amino-3-phenyl-1-thioethylpropane
  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：

  N-Boc-L-苯丙氨醇 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-amino-3-phenyl-1-thioethylpropane
  参考文献：
  名称：

  New Chiral Auxiliaries for the Construction of Quaternary Stereocenters by Copper-Catalyzed Michael Reactions

  摘要：

  DOI：

  10.1002/1521-3773(20000804)39:15<2752::aid-anie2752>3.0.co;2-5

文献信息

• New Auxiliaries for Copper-Catalyzed Asymmetric Michael Reactions: Generation of Quaternary Stereocenters at Room Temperature
  作者：Jens Christoffers、Alexander Mann

  DOI：10.1002/1521-3765(20010302)7:5<1014::aid-chem1014>3.0.co;2-x

  日期：2001.3.2

  Dialkyl amides of L-valine, L-isoleucine, and L-tert-leucine (2) are excellent chiral auxiliaries for the construction of quaternary stereocenters at ambient temperature. Enaminoesters 3, prepared from these auxiliaries 2 and Michael donors 1, undergo a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone (MVK, 4) to afford products 5 in 70-90% yield and 90-99% ee (enantiomeric excess)

  L-缬氨酸、L-异亮氨酸和 L-叔亮氨酸 (2) 的二烷基酰胺是在环境温度下构建四元立体中心的极佳手性助剂。由这些助剂 2 和迈克尔供体 1 制备的烯胺酯 3 与甲基乙烯基酮 (MVK, 4) 进行铜催化的不对称迈克尔反应，以 70-90% 的产率和 90-99% 的 ee（对映体过量）提供产物 5 . 不需要排除水分或氧气。助剂2可通过标准程序容易地获得。后处理后，它们几乎可以定量回收。
• New Chiral Auxiliaries for the Construction of Quaternary Stereocenters by Copper-Catalyzed Michael Reactions
  作者：Jens Christoffers、Alexander Mann

  DOI：10.1002/1521-3773(20000804)39:15<2752::aid-anie2752>3.0.co;2-5

  日期：2000.8.4
• 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.