(±)-allyl 2-methyl-3-(methyl(phenyl)amino)-3-oxopropanoate | 1319768-56-3

• 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: (±)-allyl 2-methyl-3-(methyl(phenyl)amino)-3-oxopropanoate
• 英文别名: allyl 2-methyl-3-(methyl(phenyl)amino)-3-oxopropanoate
• CAS: 1319768-56-3
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: VXGLAZAFVZYYAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (±)-allyl 2-methyl-3-(methyl(phenyl)amino)-3-oxopropanoate 在 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 以75%的产率得到allyl 1,3-dimethyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  通过sp（2）CH和sp（3）CH键的“无过渡金属”分子内脱氢偶联（IDC）合成2-氧吲哚。

  摘要：

  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。

  DOI：

  10.3762/bjoc.12.111
• 作为产物：
  描述：

  monoallyl malonate 在 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.08h， 生成 (±)-allyl 2-methyl-3-(methyl(phenyl)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

• Asymmetric Decarboxylative Allylation of Oxindoles
  作者：Vilius Franckevičius、James D. Cuthbertson、Mark Pickworth、David S. Pugh、Richard J. K. Taylor

  DOI：10.1021/ol201613a

  日期：2011.8.19

  An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.
• 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.