(1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-hydroxy-1-methylethyl]-4-methylbenzenesulfonamide | 497968-31-7

• 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: (1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-hydroxy-1-methylethyl]-4-methylbenzenesulfonamide
• 英文别名: N-benzyl-N-[(1S,2S)-1-hydroxy-1-(5-methylfuran-2-yl)propan-2-yl]-4-methylbenzenesulfonamide
• CAS: 497968-31-7
• 化学式: C₂₂H₂₅NO₄S
• 分子量: 399.511
• InChiKey: SHRQXZXNLSFZJE-AVRDEDQJSA-N

物化性质

• 沸点：
  552.6±60.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三苯基氯硅烷 、 (1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-hydroxy-1-methylethyl]-4-methylbenzenesulfonamide 生成 (1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-triphenylsilanyloxy-1-methylethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Asymmetric addition of 2-methylfuran and its lithiated derivative to variously N,N-protected l-alaninals

  摘要：

  The asymmetric reaction of 2-methylfuran 2a and its lithiated derivative 2b with N,N-diprotected L-alaninals 1a-c, carried out under high pressure conditions in the presence of Lewis acid-catalyst, are described. For aldehyde la two diastereoisomeric adducts anti-3a and syn-3a were formed, with predominance of the former. In the case of aldehydes 1b and 1c only the anti-diastereoisomers 3b or 3c were formed, but accompanied by two diastereoisomeric oxazolidinones trans-4 and cis-4. The absolute configuration (via X-ray analysis of anti-5 and chemical correlations) and the extent of asymmetric induction were established. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00545-1
• 作为产物：
  描述：

  N-benzyl-N-benzyloxycarbonyl-L-alaninal 在 palladium on activated charcoal 正丁基锂 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-hydroxy-1-methylethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Asymmetric addition of 2-methylfuran and its lithiated derivative to variously N,N-protected l-alaninals

  摘要：

  The asymmetric reaction of 2-methylfuran 2a and its lithiated derivative 2b with N,N-diprotected L-alaninals 1a-c, carried out under high pressure conditions in the presence of Lewis acid-catalyst, are described. For aldehyde la two diastereoisomeric adducts anti-3a and syn-3a were formed, with predominance of the former. In the case of aldehydes 1b and 1c only the anti-diastereoisomers 3b or 3c were formed, but accompanied by two diastereoisomeric oxazolidinones trans-4 and cis-4. The absolute configuration (via X-ray analysis of anti-5 and chemical correlations) and the extent of asymmetric induction were established. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00545-1

文献信息

• Asymmetric addition of 2-methylfuran and its lithiated derivative to variously N,N-protected l-alaninals
  作者：Elżbieta Kobrzycka、Dorota Gryko、Janusz Jurczak

  DOI：10.1016/s0957-4166(02)00545-1

  日期：2002.10

  The asymmetric reaction of 2-methylfuran 2a and its lithiated derivative 2b with N,N-diprotected L-alaninals 1a-c, carried out under high pressure conditions in the presence of Lewis acid-catalyst, are described. For aldehyde la two diastereoisomeric adducts anti-3a and syn-3a were formed, with predominance of the former. In the case of aldehydes 1b and 1c only the anti-diastereoisomers 3b or 3c were formed, but accompanied by two diastereoisomeric oxazolidinones trans-4 and cis-4. The absolute configuration (via X-ray analysis of anti-5 and chemical correlations) and the extent of asymmetric induction were established. (C) 2002 Published by Elsevier Science Ltd.