dimethyl (2S)-1-trityl-2,5-dihydropyrrole-2,3-dicarboxylate | 401909-81-7

• 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: dimethyl (2S)-1-trityl-2,5-dihydropyrrole-2,3-dicarboxylate
• CAS: 401909-81-7
• 化学式: C₂₇H₂₅NO₄
• 分子量: 427.5
• InChiKey: NCZGFGGSDWTVQY-DEOSSOPVSA-N

物化性质

• 沸点：
  516.8±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (2S)-1-trityl-2,5-dihydropyrrole-2,3-dicarboxylate 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
  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：

  甲醇 、 一氧化碳 、 (S)-methyl 3-(trifluoromethylsulfonyloxy)-1-trityl-2,5-dihydro-1H-pyrrole-2-carboxylate 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate TEA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以67%的产率得到dimethyl (2S)-1-trityl-2,5-dihydropyrrole-2,3-dicarboxylate
  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.