methyl (2S)-3-phenyl-1-trityl-2,5-dihydropyrrole-2-carboxylate | 401909-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl (2S)-3-phenyl-1-trityl-2,5-dihydropyrrole-2-carboxylate
• CAS: 401909-65-7
• 化学式: C₃₁H₂₇NO₂
• 分子量: 445.561
• InChiKey: RADJTHVSKBBGTP-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-phenyl-1-trityl-2,5-dihydropyrrole-2-carboxylate 在 palladium on activated charcoal 盐酸 、 甲醇 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 cis-3-phenyl-L-proline methyl ester hydrochloride
  参考文献：
  名称：

  Enantioselective approach to 3-substituted prolines

  摘要：

  Enantio selective synthesis of 3-substituted prolines was achieved starting from commercially available 3-hydroxy-(S)-2-proline. Palladium-mediated couplings were used to introduce a variety of groups at C3 using the corresponding enol triflate derived from N-trityl 3-oxo-(S)-2-proline methyl ester. Cleavage of the trityl residue and hydrogenation provided final products with good to modest diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01869-x
• 作为产物：
  描述：

  甲基(3S)-3-羟基-L-脯氨酸酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 三甲基氯硅烷 、 四丙基高钌酸铵 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.0h， 生成 methyl (2S)-3-phenyl-1-trityl-2,5-dihydropyrrole-2-carboxylate
  参考文献：
  名称：

  Enantioselective approach to 3-substituted prolines

  摘要：

  Enantio selective synthesis of 3-substituted prolines was achieved starting from commercially available 3-hydroxy-(S)-2-proline. Palladium-mediated couplings were used to introduce a variety of groups at C3 using the corresponding enol triflate derived from N-trityl 3-oxo-(S)-2-proline methyl ester. Cleavage of the trityl residue and hydrogenation provided final products with good to modest diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01869-x

文献信息

• Enantioselective approach to 3-substituted prolines
  作者：Theodore M Kamenecka、You-Jung Park、Linus S Lin、Thomas Lanza、William K Hagmann

  DOI：10.1016/s0040-4039(01)01869-x

  日期：2001.12

  Enantio selective synthesis of 3-substituted prolines was achieved starting from commercially available 3-hydroxy-(S)-2-proline. Palladium-mediated couplings were used to introduce a variety of groups at C3 using the corresponding enol triflate derived from N-trityl 3-oxo-(S)-2-proline methyl ester. Cleavage of the trityl residue and hydrogenation provided final products with good to modest diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.