(E)-3,7-dimethylocta-2,6-dien-1-yl 3-allyl-1-methyl-2-oxoindoline-3-carboxylate | 1410941-06-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-3,7-dimethylocta-2,6-dien-1-yl 3-allyl-1-methyl-2-oxoindoline-3-carboxylate
• 英文别名: (±)-(E)-3,7-dimethylocta-2,6-dien-1-yl 3-allyl-1-methyl-2-oxoindoline-3-carboxylate
• CAS: 1410941-06-8
• 化学式: C₂₃H₂₉NO₃
• 分子量: 367.488
• InChiKey: UGHKYYUEZSIKMI-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (E)-3,7-dimethylocta-2,6-dien-1-yl 3-(methyl(phenyl)amino)-3-oxopropanoate 在 potassium tert-butylate 、 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-3,7-dimethylocta-2,6-dien-1-yl 3-allyl-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

文献信息

• DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids
  作者：Subhajit Bhunia、Santanu Ghosh、Dhananjay Dey、Alakesh Bisai

  DOI：10.1021/ol400899e

  日期：2013.5.17

  An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.