(2R,5S)-1-(tert-butoxycarbonyl)-2-(p-carbomethoxyamino-phenyl)-5-hydroxymethyl-3-pyrroline | 501096-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (2R,5S)-1-(tert-butoxycarbonyl)-2-(p-carbomethoxyamino-phenyl)-5-hydroxymethyl-3-pyrroline
• 英文别名: tert-butyl (2S,5R)-2-(hydroxymethyl)-5-[4-(methoxycarbonylamino)phenyl]-2,5-dihydropyrrole-1-carboxylate
• CAS: 501096-29-3
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: KZJZVOVAVXRAKX-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5S)-1-(tert-butoxycarbonyl)-2-(p-carbomethoxyamino-phenyl)-5-hydroxymethyl-3-pyrroline 在 盐酸 、 potassium osmate(VI) 、 N-甲基吗啉氧化物 、 乙酰氯 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 33.5h， 生成 (2S,3S,4R,5R)-2-(4-aminophenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2S,5R)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside

  摘要：

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.

  DOI：

  10.1021/ol027268a
• 作为产物：
  描述：

  (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 sodium acetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.5h， 生成 (2R,5S)-1-(tert-butoxycarbonyl)-2-(p-carbomethoxyamino-phenyl)-5-hydroxymethyl-3-pyrroline
  参考文献：
  名称：

  Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2S,5R)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside

  摘要：

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.

  DOI：

  10.1021/ol027268a

文献信息

• Stereoselective Synthesis of Aza Analogues of Isoaltholactone and Goniothalesdiol - New Applications of the Heck-Matsuda Reaction
  作者：Angélica Venturini Moro、Marcelo Rodrigues dos Santos、Carlos Roque D. Correia

  DOI：10.1002/ejoc.201100886

  日期：2011.12

  The synthesis of (–)-aza-isoaltholactone 6 was successfully accomplished in nine steps from the starting enecarbamate. We also performed the synthesis of the new fully substituted pyrrolidine (–)-(2R,3R,4S,5S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-5-phenylpyrrolidin-2-ylacrylic acid 28, which is a potential advanced intermediate in the route to aza-altholactone. Moreover, the synthesis of a new nitrogen

  描述了具有生物活性的异戊内酯和goniothalesdiol 的氮类似物的立体选择性合成。成功的策略是在合成的早期阶段以不同的方式在带有酯官能团的手性内环烯氨基甲酸酯和重氮芳烃四氟硼酸盐之间进行 Heck-Matsuda 反应。讨论了与这种关键芳基化反应相关的几个方面，以突出影响芳基化过程结果的结构特征。(-) - aza-isoaltholactone 6 的合成从起始烯氨基甲酸酯分九步成功完成。我们还合成了新的完全取代的吡咯烷 (-) - (2R, 3R, 4S, 5S) -1- (叔丁氧基羰基) -3,4-二羟基-5-苯基吡咯烷-2-基丙烯酸 28，它是氮杂-内酯路线中潜在的高级中间体。此外，从受保护的二羟基吡咯烷 (-) - 27 合成了一种新的goniothalesdiol (+) - 33 的氮类似物，该二羟基吡咯烷 (-) - 27 是通过尝试合成 aza-altholactone
• Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2<i>S</i>,5<i>R</i>)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside
  作者：Elias A. Severino、Edson R. Costenaro、Ariel L. L. Garcia、Carlos Roque D. Correia

  DOI：10.1021/ol027268a

  日期：2003.2.1

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.