(S)-2-((S)-azido(phenyl)methyl)-1-tritylpyrrolidine | 1608091-96-8

• 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: (S)-2-((S)-azido(phenyl)methyl)-1-tritylpyrrolidine
• CAS: 1608091-96-8
• 化学式: C₃₀H₂₈N₄
• 分子量: 444.579
• InChiKey: OKXZPADYNOGHCV-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-azido(phenyl)methyl)-1-tritylpyrrolidine 在 盐酸 、 水 、 potassium carbonate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-2-((S)-azido(phenyl)methyl)-1-ethylpyrrolidine
  参考文献：
  名称：

  New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins

  摘要：

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.011
• 作为产物：
  描述：

  (αR,2S)-α-phenyl-1-triphenylmethyl-2-pyrrolidinemethanol 在 叠氮磷酸二苯酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以80%的产率得到(S)-2-((S)-azido(phenyl)methyl)-1-tritylpyrrolidine
  参考文献：
  名称：

  New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins

  摘要：

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.011

文献信息

• Role of Configuration at C6 in Catalytic Activity of <scp>l</scp>-Proline-Derived Bifunctional Organocatalysts
  作者：Hui Jin、Soo Min Cho、Juyeol Lee、Do Hyun Ryu

  DOI：10.1021/acs.orglett.7b01000

  日期：2017.5.5

  chiral bifunctional (thio)urea organocatalysts epi-PTU and epi-PU were newly synthesized, and their catalytic performances were compared with their C6 epimeric catalysts PTU and PU in various Michael reactions of nitrostyrene in terms of reactivities and stereoselectivities. The experimental results indicate that a proper relative stereochemistry at C2 and C6 in l-proline-derived bifunctional organocatalysts

  合成了1-脯氨酸衍生的手性双官能（硫）脲有机催化剂epi - PTU和epi - PU，并将它们的催化性能与C6差向异构催化剂PTU和PU在硝基苯乙烯的各种迈克尔反应中进行了反应性和立体选择性方面的比较。实验结果表明，1-脯氨酸衍生的双官能有机催化剂在C2和C6处的适当相对立体化学对于成功催化非常重要，并且具有2 S，6 R的催化剂（PTU和PU） 配置效率更高。