(S,E)-benzyl (3-methyl-1-((4-oxopent-2-en-1-yl)oxy)butan-2-yl)carbamate | 1334324-40-1

• 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: (S,E)-benzyl (3-methyl-1-((4-oxopent-2-en-1-yl)oxy)butan-2-yl)carbamate
• 英文别名: benzyl N-[(2S)-3-methyl-1-[(E)-4-oxohex-2-enoxy]butan-2-yl]carbamate
• CAS: 1334324-40-1
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: SRICZMNDAQRSNX-VEGGFIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,E)-benzyl (3-methyl-1-((4-oxopent-2-en-1-yl)oxy)butan-2-yl)carbamate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (3S,5S)-benzyl 3-isopropyl-5-(2-oxobutyl)morpholine-4-carboxylate 、 (3S,5R)-benzyl 3-isopropyl-5-(2-oxobutyl)morpholine-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
• 作为产物：
  描述：

  Cbz-L-缬氨醇 在 Hoveyda-Grubbs catalyst second generation 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.42h， 生成 (S,E)-benzyl (3-methyl-1-((4-oxopent-2-en-1-yl)oxy)butan-2-yl)carbamate
  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

• Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts
  作者：Cheng Zhong、Yikai Wang、Alvin W. Hung、Stuart L. Schreiber、Damian W. Young

  DOI：10.1021/ol202276h

  日期：2011.10.21

  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.