(3S,5R)-benzyl 3-benzyl-5-(2-oxopropyl)thiomorpholine-4-carboxylate | 1427030-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,5R)-benzyl 3-benzyl-5-(2-oxopropyl)thiomorpholine-4-carboxylate
• CAS: 1427030-85-0
• 化学式: C₂₂H₂₅NO₃S
• 分子量: 383.511
• InChiKey: CBGVCZXAILGTPY-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,5R)-benzyl 3-benzyl-5-(2-oxopropyl)thiomorpholine-4-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 1-((3R,5S)-5-benzyl-1,1-dioxidothiomorpholin-3-yl)propan-2-one
  参考文献：
  名称：

  Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts

  摘要：

  An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) complex or strong Bronsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.

  DOI：

  10.1021/ol202276h
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 Hoveyda-Grubbs catalyst second generation 、 四溴化碳 、 三氟甲磺酸 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (3S,5R)-benzyl 3-benzyl-5-(2-oxopropyl)thiomorpholine-4-carboxylate
  参考文献：
  名称：

  Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts

  摘要：

  An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) complex or strong Bronsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.

  DOI：

  10.1021/ol202276h

文献信息

• Synthesis of Substituted Morpholines Using Stereodivergent Aza-Michael Reactions Catalyzed by Brønsted Acids
  作者：Cheng Zhong、Yikai Wang、Conor O’Herin、Damian W. Young

  DOI：10.1021/cs400031p

  日期：2013.4.5

  A diastereoselective intramolecular aza-Michael reaction between N-Cbz carbamates and enones was studied. The investigation revealed that Bronsted acids with different strengths produce different diastereomers. The catalysts TfOH and TFA were used to generate differential outcomes in the aza-Michael reaction.