(E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-1-methyl-2-oxoindoline-3-carboxylate | 1410940-98-5

• 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)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-1-methyl-2-oxoindoline-3-carboxylate
• 英文别名: (±)-(E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-1-methyl-2-oxoindoline-3-carboxylate
• CAS: 1410940-98-5
• 化学式: C₂₁H₂₇NO₃
• 分子量: 341.45
• InChiKey: UTFNBXRCMBGDCB-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-(N-甲基-N-苯基氨基)-3-氧代丙酸甲酯 在 potassium tert-butylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-1-methyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids

  摘要：

  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.

  DOI：

  10.1021/ol400899e

文献信息

• Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds
  作者：Zheng-Jian Wu、Shi-Rui Li、Hao Long、Hai-Chao Xu

  DOI：10.1039/c8cc02472c

  日期：——

  The intramolecular C(sp3)–H/C(sp2)–H cross-coupling of 1,3-dicarbonyl compounds has been achieved through Cp2Fe-catalyzed electrochemical oxidation. The key to the success of these dehydrogenative cyclization reactions is the selective activation of the acidic α-C–H bond of the 1,3-dicarbonyl moiety to generate a carbon-centered radical.

  1,3-二羰基化合物的分子内C（sp 3）–H / C（sp 2）–H交叉偶联是通过Cp 2 Fe催化的电化学氧化实现的。这些脱氢环化反应成功的关键是选择性激活1,3-二羰基部分的酸性α-C–H键以生成一个以碳为中心的自由基。
• 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.