(E)-methyl 3-(but-2-enyl(t-butyl)amino)-3-oxopropanoate | 1226792-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-methyl 3-(but-2-enyl(t-butyl)amino)-3-oxopropanoate
• 英文别名: methyl 3-[[(E)-but-2-enyl]-tert-butylamino]-3-oxopropanoate
• CAS: 1226792-43-3
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: MRAMSFQGPCNYEG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯基氯化硒 、 (E)-methyl 3-(but-2-enyl(t-butyl)amino)-3-oxopropanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 4.33h， 以60%的产率得到(E)-methyl 3-(but-2-enyl(t-butyl)amino)-3-oxo-2-(phenylseleno)propanoate
  参考文献：
  名称：

  Selective Approach toward Multifunctionalized Lactams by Lewis Acid Promoted PhSe Group Transfer Radical Cyclization

  摘要：

  We have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of alpha-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf)(3)) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure.

  DOI：

  10.1021/jo100139u
• 作为产物：
  描述：

  (E)-N-tert-butylbut-2-en-1-amine 、 monomethyl monopotassium malonate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(E)-methyl 3-(but-2-enyl(t-butyl)amino)-3-oxopropanoate
  参考文献：
  名称：

  Selective Approach toward Multifunctionalized Lactams by Lewis Acid Promoted PhSe Group Transfer Radical Cyclization

  摘要：

  We have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of alpha-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf)(3)) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure.

  DOI：

  10.1021/jo100139u

文献信息

• Selective Approach toward Multifunctionalized Lactams by Lewis Acid Promoted PhSe Group Transfer Radical Cyclization
  作者：Jin-Di Yu、Wei Ding、Gao-Yan Lian、Ke-Sheng Song、Dan-Wei Zhang、Xiang Gao、Dan Yang

  DOI：10.1021/jo100139u

  日期：2010.5.21

  We have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of alpha-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf)(3)) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure.