benzyl 3-{1-[benzyl(hydroxy)amino]cyclohexyl}but-3-enoate | 1373129-20-4

• 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 3-{1-[benzyl(hydroxy)amino]cyclohexyl}but-3-enoate
• 英文别名: Benzyl 3-[1-[benzyl(hydroxy)amino]cyclohexyl]but-3-enoate；benzyl 3-[1-[benzyl(hydroxy)amino]cyclohexyl]but-3-enoate
• CAS: 1373129-20-4
• 化学式: C₂₄H₂₉NO₃
• 分子量: 379.499
• InChiKey: POAZCFFWYSTCRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苄基环己亚胺氧化物 、 buta-2,3-dienoic acid benzyl ester 在 samarium diiodide 、 lithium bromide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以26%的产率得到benzyl 3-{1-[benzyl(hydroxy)amino]cyclohexyl}but-3-enoate
  参考文献：
  名称：

  SmI₂-Mediated Coupling of Nitrones and tert-Butanesulfinyl Imines with Allenoates: Synthesis of β-Methylenyl-γ-lactams and Tetramic Acids

  摘要：

  Nitrones and tert-butanesulfinyl imines undergo conjugate addition to alkyl allenoates under SmI2-mediated reductive coupling conditions to produce novel beta-methylenyl-substituted gamma-amino esters. The latter were readily transformed into the corresponding beta-methylenyl-gamma-lactams by simple zinc reduction (N-hydroxy amines) or by acid hydrolysis (sulfinamides). The diastereoselective preparation of various beta-methylenyl-gamma-lactams offers a route to tetramic acids, the key structural features of an important class of bioactive natural products.

  DOI：

  10.1021/ol300550x

文献信息

• SmI₂-Mediated Coupling of Nitrones and <i>tert</i>-Butanesulfinyl Imines with Allenoates: Synthesis of β-Methylenyl-γ-lactams and Tetramic Acids
  作者：Chu-Pei Xu、Pei-Qiang Huang、Sandrine Py

  DOI：10.1021/ol300550x

  日期：2012.4.20

  Nitrones and tert-butanesulfinyl imines undergo conjugate addition to alkyl allenoates under SmI2-mediated reductive coupling conditions to produce novel beta-methylenyl-substituted gamma-amino esters. The latter were readily transformed into the corresponding beta-methylenyl-gamma-lactams by simple zinc reduction (N-hydroxy amines) or by acid hydrolysis (sulfinamides). The diastereoselective preparation of various beta-methylenyl-gamma-lactams offers a route to tetramic acids, the key structural features of an important class of bioactive natural products.