(S)-2-Phenyl-2-(toluene-4-sulfonylamino)-pent-4-enoic acid methyl ester | 848829-67-4

• 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-Phenyl-2-(toluene-4-sulfonylamino)-pent-4-enoic acid methyl ester
• 英文别名: methyl (2S)-2-[(4-methylphenyl)sulfonylamino]-2-phenylpent-4-enoate
• CAS: 848829-67-4
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: PYPJHJGGGQEBJN-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-Phenyl-2-(toluene-4-sulfonylamino)-pent-4-enoic acid methyl ester 在 碘 、 sodium hydride 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (2S,4R)-4-Hydroxy-2-phenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 4-hydroxy-2-phenylproline framework

  摘要：

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.130
• 作为产物：
  描述：

  (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-pent-4-enoic acid tert-butyl ester 在 N,N,N',N'-四甲基-1,6-己二胺 、 硫酸 作用下， 以 乙腈 为溶剂， 生成 (S)-2-Phenyl-2-(toluene-4-sulfonylamino)-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 4-hydroxy-2-phenylproline framework

  摘要：

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.130

文献信息

• Stereoselective synthesis of 4-hydroxy-2-phenylproline framework
  作者：Kenji Maeda、Ross A. Miller、Ronald H. Szumigala、Ali Shafiee、Sandor Karady、Joseph D. Armstrong

  DOI：10.1016/j.tetlet.2004.12.130

  日期：2005.2

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.