(2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline | 501096-26-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S)-5-phenyl-2,5-dihydropyrrole-1,2-dicarboxylate
• CAS: 501096-26-0
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: FRSSUBNNRGPIKG-KZUDCZAMSA-N

物化性质

• 沸点：
  395.5±42.0 °C(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline 在 10 percent Pd/C 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate
  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：

  benzenediazonium tetrafluoroborate 、 (S)-2,3-二氢-1H-吡咯-1,2-二甲酸 1-叔丁基 2-甲基酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以70%的产率得到(2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-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

• Chiral Triphenylprolinol Ligands for the Efficient Catalytic Asymmetric Arylation of Aldehydes
  作者：Angélica Venturini Moro、Edward R. T. Tiekink、Julio Zukerman-Schpector、Diogo S. Lüdtke、Carlos Roque D. Correia

  DOI：10.1002/ejoc.201000336

  日期：2010.7

  The synthesis of new chiral amino alcohols by Heck arylation of an enecarbamate is described. These compounds were used as chiral ligands for the catalytic asymmetric arylation of aldehydes and can be easily recovered. Chiral, nonracemic diarylmethanols were obtained in high yields and enantioselectivities.

  描述了通过烯氨基甲酸酯的 Heck 芳基化合成新的手性氨基醇。这些化合物被用作醛的催化不对称芳基化的手性配体，并且可以很容易地回收。以高产率和对映选择性获得手性、非外消旋二芳基甲醇。
• 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