benzyl [(3S,6S,9aR)-5-oxo-3-phenyloctahydro[1,3]oxazolo[3,2-a]azepin-6-yl]carbamate | 1196714-47-2

• 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: benzyl [(3S,6S,9aR)-5-oxo-3-phenyloctahydro[1,3]oxazolo[3,2-a]azepin-6-yl]carbamate
• 英文别名: benzyl N-[(3S,6S,9aR)-5-oxo-3-phenyl-3,6,7,8,9,9a-hexahydro-2H-[1,3]oxazolo[3,2-a]azepin-6-yl]carbamate
• CAS: 1196714-47-2
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: UHPYBNNZPGAAQP-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 L-苯甘氨醇 、 benzyl (1S)-1-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}but-3-enylcarbamate 在 dicarbonylacetylacetonato rhodium(I) 、 氢气 、 对甲苯磺酸 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 以 四氢呋喃 为溶剂， 70.0 ℃ 、1.0 MPa 条件下， 反应 1.0h， 以65%的产率得到benzyl [(3S,6S,9aR)-5-oxo-3-phenyloctahydro[1,3]oxazolo[3,2-a]azepin-6-yl]carbamate
  参考文献：
  名称：

  Four-Component Reactions toward Fused Heterocyclic Rings

  摘要：

  A multicomponent reaction between H-2, CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered, This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using pi-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.

  DOI：

  10.1021/ol902279m

文献信息

• Four-Component Reactions toward Fused Heterocyclic Rings
  作者：Etienne Airiau、Nicolas Girard、André Mann、Jessica Salvadori、Maurizio Taddei

  DOI：10.1021/ol902279m

  日期：2009.11.19

  A multicomponent reaction between H-2, CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered, This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using pi-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.