N-[2-((R)-1-Hydroxymethyl-propylamino)-ethyl]-4-methyl-benzenesulfonamide | 152877-82-2

• 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: N-[2-((R)-1-Hydroxymethyl-propylamino)-ethyl]-4-methyl-benzenesulfonamide
• 英文别名: N-[2-[[(2R)-1-hydroxybutan-2-yl]amino]ethyl]-4-methylbenzenesulfonamide
• CAS: 152877-82-2
• 化学式: C₁₃H₂₂N₂O₃S
• 分子量: 286.395
• InChiKey: PFAZTQIFHMWLLJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  86.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 N-[2-((R)-1-Hydroxymethyl-propylamino)-ethyl]-4-methyl-benzenesulfonamide 在 吡啶 、 sodium hydride 作用下， 生成 (R)-1,4-Bis(p-tolylsulfonyl)-2-ethylpiperazine
  参考文献：
  名称：

  Catalytic asymmetric construction of morpholines and piperazines by palladium-catalyzed tandem allylic substitution reactions

  摘要：

  Reaction of 1,4-diacetoxy-cis-2-butene (1a) with 2-(benzylamino)ethanol (2a) was catalyzed by a palladium complex (5 mol %) coordinated with (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl to give optically active (R)-4-benzyl-2-vinylmorpholine (3a) of up to 65% ee. Optically active 1,4-bis(p-tolylsulfonyl)-2-vinylpiperazine (7a) (60% ee) was also obtained from 1,4-dicarbomethoxy-2-butene (1b) and 1,2-bis[(p-tolylsulfonyl)amino]ethane (6a) in a similar manner. This cyclization proceeds through a tandem allylic substitution via pi-allylpalladium intermediates. The palladium-catalyzed reaction with 2-amino-1,3-propanediols 17 gave 2-vinyl-5-(hydroxymethyl)morpholines of up to 73 % ee.

  DOI：

  10.1021/jo00076a052
• 作为产物：
  描述：

  2-氨基丁醇 、 2-(tosylamino)ethyl p-toluenesulfonate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 生成 N-[2-((R)-1-Hydroxymethyl-propylamino)-ethyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Catalytic asymmetric construction of morpholines and piperazines by palladium-catalyzed tandem allylic substitution reactions

  摘要：

  Reaction of 1,4-diacetoxy-cis-2-butene (1a) with 2-(benzylamino)ethanol (2a) was catalyzed by a palladium complex (5 mol %) coordinated with (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl to give optically active (R)-4-benzyl-2-vinylmorpholine (3a) of up to 65% ee. Optically active 1,4-bis(p-tolylsulfonyl)-2-vinylpiperazine (7a) (60% ee) was also obtained from 1,4-dicarbomethoxy-2-butene (1b) and 1,2-bis[(p-tolylsulfonyl)amino]ethane (6a) in a similar manner. This cyclization proceeds through a tandem allylic substitution via pi-allylpalladium intermediates. The palladium-catalyzed reaction with 2-amino-1,3-propanediols 17 gave 2-vinyl-5-(hydroxymethyl)morpholines of up to 73 % ee.

  DOI：

  10.1021/jo00076a052

文献信息

• Catalytic asymmetric construction of morpholines and piperazines by palladium-catalyzed tandem allylic substitution reactions
  作者：Yasuhiro Uozumi、Asako Tanahashi、Tamio Hayashi

  DOI：10.1021/jo00076a052

  日期：1993.11

  Reaction of 1,4-diacetoxy-cis-2-butene (1a) with 2-(benzylamino)ethanol (2a) was catalyzed by a palladium complex (5 mol %) coordinated with (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl to give optically active (R)-4-benzyl-2-vinylmorpholine (3a) of up to 65% ee. Optically active 1,4-bis(p-tolylsulfonyl)-2-vinylpiperazine (7a) (60% ee) was also obtained from 1,4-dicarbomethoxy-2-butene (1b) and 1,2-bis[(p-tolylsulfonyl)amino]ethane (6a) in a similar manner. This cyclization proceeds through a tandem allylic substitution via pi-allylpalladium intermediates. The palladium-catalyzed reaction with 2-amino-1,3-propanediols 17 gave 2-vinyl-5-(hydroxymethyl)morpholines of up to 73 % ee.