methyl 3-(t-butyl(cyclohex-2-enyl)amino)-3-oxo-2-(phenylseleno)propanoate | 1226792-41-1

• 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: methyl 3-(t-butyl(cyclohex-2-enyl)amino)-3-oxo-2-(phenylseleno)propanoate
• 英文别名: Methyl 3-[tert-butyl(cyclohex-2-en-1-yl)amino]-3-oxo-2-phenylselanylpropanoate
• CAS: 1226792-41-1
• 化学式: C₂₀H₂₇NO₃Se
• 分子量: 408.399
• InChiKey: PASDRSHKPJUPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methyl 3-(t-butyl(cyclohex-2-enyl)amino)-3-oxo-2-(phenylseleno)propanoate 在 ytterbium(III) triflate 作用下， 以 乙醚 为溶剂， 以84%的产率得到methyl cis-1-tert-butyl-2-oxo-cis-4-(phenylseleno)-octahydro-1H-indole-cis-3-carboxylate
  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：

  苯基氯化硒 、 methyl 3-(t-butyl(cyclohex-2-enyl)amino)-3-oxopropanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 4.33h， 以68%的产率得到methyl 3-(t-butyl(cyclohex-2-enyl)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

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.