(R)-1-Fluoromethyl-2-((R)-toluene-4-sulfinyl)-ethylamine | 197085-99-7

• 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: (R)-1-Fluoromethyl-2-((R)-toluene-4-sulfinyl)-ethylamine
• CAS: 197085-99-7
• 化学式: C₁₀H₁₄FNOS
• 分子量: 215.292
• InChiKey: YIOSDGPUHSQLEN-YMTOWFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-1-Fluoromethyl-2-((R)-toluene-4-sulfinyl)-ethylamine 在 2,4,6-三甲基吡啶 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  Stereoselective synthesis of the antibacterial 3-fluoro-d-alanine

  摘要：

  The wide spectrum antibacterial 3-fluoro-D-alanine (S)-9 has been stereoselectively synthesized via ''chiral sulfoxide chemistry''. Key steps are the azidation of the alpha-fluoro alpha'-sulfinyl alcohol (2S,R-s)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz alpha-sulfinyl amine (2R,R-s)-5 into the N-Cbz aminoalcohol (S)-7, through a ''non-oxidative Pummerer reaction''. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00334-0
• 作为产物：
  描述：

  (2S,R_S)-β-fluoromethyl-β-hydroxy sulfoxide 在 1,3-丙二硫醇 、 sodium azide 、 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 生成 (R)-1-Fluoromethyl-2-((R)-toluene-4-sulfinyl)-ethylamine
  参考文献：
  名称：

  Stereoselective synthesis of the antibacterial 3-fluoro-d-alanine

  摘要：

  The wide spectrum antibacterial 3-fluoro-D-alanine (S)-9 has been stereoselectively synthesized via ''chiral sulfoxide chemistry''. Key steps are the azidation of the alpha-fluoro alpha'-sulfinyl alcohol (2S,R-s)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz alpha-sulfinyl amine (2R,R-s)-5 into the N-Cbz aminoalcohol (S)-7, through a ''non-oxidative Pummerer reaction''. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00334-0

文献信息

• Stereoselective synthesis of the antibacterial 3-fluoro-d-alanine
  作者：Pierfrancesco Bravo、Giancarlo Cavicchio、Marcello Crucianelli、Andrea Poggiali、Matteo Zanda

  DOI：10.1016/s0957-4166(97)00334-0

  日期：1997.8

  The wide spectrum antibacterial 3-fluoro-D-alanine (S)-9 has been stereoselectively synthesized via ''chiral sulfoxide chemistry''. Key steps are the azidation of the alpha-fluoro alpha'-sulfinyl alcohol (2S,R-s)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz alpha-sulfinyl amine (2R,R-s)-5 into the N-Cbz aminoalcohol (S)-7, through a ''non-oxidative Pummerer reaction''. (C) 1997 Published by Elsevier Science Ltd.