tert-butyl 5-(2-ethoxy-2-oxoethyl)-3,4-dihydropyridine-1(2H)-carboxylate | 1268245-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl 5-(2-ethoxy-2-oxoethyl)-3,4-dihydropyridine-1(2H)-carboxylate
• 英文别名: tert-butyl 5-(2-ethoxy-2-oxoethyl)-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 1268245-92-6
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: MSZFLLHFCKDZPK-UHFFFAOYSA-N

物化性质

• 沸点：
  356.5±42.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-(2-ethoxy-2-oxoethyl)-3,4-dihydropyridine-1(2H)-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 生成 1-O-tert-butyl 2-O-methyl 3-(2-methoxy-2-oxoethyl)piperidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines

  摘要：

  A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.131
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl 5-(2-ethoxy-2-oxoethyl)-3,4-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines

  摘要：

  A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.131

文献信息

• β-C(sp²)–H alkylation of enamides using xanthate chemistry
  作者：Sylvain Bertho、Ismaël Dondasse、Pascal Retailleau、Cyril Nicolas、Isabelle Gillaizeau

  DOI：10.1039/d0nj01209b

  日期：——

  Access to the γ-amino-β,γ-unsaturated acyl scaffold was established by applying xanthate chemistry to enamides. This original β-C(sp2)–H alkylation is regioselective and exhibits broad substrate scope and good functional group tolerance. The large availability of xanthates is advantageous to the scope of the reaction which combines a radical process and a polar reaction.

  通过将黄药化学方法应用于酰胺，可以建立对γ-氨基-β，γ-不饱和酰基支架的访问。最初的β-C（sp 2）–H烷基化具有区域选择性，并具有广泛的底物范围和良好的官能团耐受性。黄原酸酯的大量可用性有利于结合自由基过程和极性反应的反应范围。