(S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide | 1403959-04-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide
• 英文别名: (2S)-1-acetyl-N-(4-methylphenyl)sulfonylpyrrolidine-2-carboxamide
• CAS: 1403959-04-5
• 化学式: C₁₄H₁₈N₂O₄S
• 分子量: 310.374
• InChiKey: FPRXAVGQCFCFRE-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙酰-L-脯氨酸 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Organocatalyzed Baylis–Hillman reaction: an enantioselective approach

  摘要：

  A convenient protocol has been developed for the synthesis of Baylis-Hillman adducts in the presence of a base and an organocatalyst. We have designed and synthesized organocatalysts based on hydrogen bonding using a pyrrolidine ring as the backbone and applied them to Baylis-Hillman transformations. This method provides products in good to high yields (73-90%) and with excellent enantiomeric excesses (up to 96%) and reasonable reaction times. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.013
• 作为试剂：
  描述：

  1-萘甲醛 、 3-溴丙烯 在 tin 、 (S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以78%的产率得到
  参考文献：
  名称：

  An efficient route for the allylation of arylaldehydes to give enantiopure homoallylic alcohols

  摘要：

  An efficient asymmetric synthesis of homoallylic alcohols is described by the allylation of carbonyl compounds using organocatalysts as chiral directors in the presence of tin metal. The effect of chiral environment is also studied on the allylation reactions. This method allows us to obtain two different enantiomers of homoallylic alcohol in the presence of the corresponding chiral compound. The protocol is applied to various aldehydes to obtain high yields and excellent enantioselectivities for the corresponding homoallylic alcohols. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.016

文献信息

• Organocatalyzed Baylis–Hillman reaction: an enantioselective approach
  作者：Prashant B. Thorat、Santosh V. Goswami、Bhimrao C. Khade、Sudhakar R. Bhusare

  DOI：10.1016/j.tetasy.2012.08.013

  日期：2012.9

  A convenient protocol has been developed for the synthesis of Baylis-Hillman adducts in the presence of a base and an organocatalyst. We have designed and synthesized organocatalysts based on hydrogen bonding using a pyrrolidine ring as the backbone and applied them to Baylis-Hillman transformations. This method provides products in good to high yields (73-90%) and with excellent enantiomeric excesses (up to 96%) and reasonable reaction times. (C) 2012 Elsevier Ltd. All rights reserved.