2-methylallyl 3-((4-methoxyphenyl)(methyl)amino)-3-oxopropanoate | 1410940-55-4

• 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: 2-methylallyl 3-((4-methoxyphenyl)(methyl)amino)-3-oxopropanoate
• 英文别名: 2-methylprop-2-enyl 3-(4-methoxy-N-methylanilino)-3-oxopropanoate
• CAS: 1410940-55-4
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: HHQVQMLETPENSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylallyl 3-((4-methoxyphenyl)(methyl)amino)-3-oxopropanoate 在 potassium tert-butylate 、 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 2-methylallyl 3-benzyl-5-methoxy-1-methyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Intramolecular Dehydrogenative Coupling of sp² C–H and sp³ C–H Bonds: An Expeditious Route to 2-Oxindoles

  摘要：

  An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.

  DOI：

  10.1021/ol302767w
• 作为产物：
  描述：

  3-(2-methylallyloxy)-3-oxopropanoic acid 、 N-甲基-P-氨基苯甲醚 在 三乙胺 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.08h， 生成 2-methylallyl 3-((4-methoxyphenyl)(methyl)amino)-3-oxopropanoate
  参考文献：
  名称：

  Intramolecular Dehydrogenative Coupling of sp² C–H and sp³ C–H Bonds: An Expeditious Route to 2-Oxindoles

  摘要：

  An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.

  DOI：

  10.1021/ol302767w

文献信息

• Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds
  作者：Nivesh Kumar、Santanu Ghosh、Subhajit Bhunia、Alakesh Bisai

  DOI：10.3762/bjoc.12.111

  日期：——

  benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of beta-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for

  经由“无过渡金属”的分子内脱氢偶联（IDC），已经完成了在假苄基位置带有全碳季中心的各种2-氧吲哚的合成。通过使用KOt-Bu催化β-N-芳基酰胺酯与烷基卤化物的一锅C-烷基化，然后脱氢偶联，通过形成碳-碳键来进行2-氧吲哚部分的构建。实验证据表明该反应朝向自由基介导的途径。
• Intramolecular Dehydrogenative Coupling of sp² C–H and sp³ C–H Bonds: An Expeditious Route to 2-Oxindoles
  作者：Santanu Ghosh、Subhadip De、Badrinath N. Kakde、Subhajit Bhunia、Amit Adhikary、Alakesh Bisai

  DOI：10.1021/ol302767w

  日期：2012.12.7

  An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.