tert-butyl 3-(methyl(phenyl)amino)-3-oxopropanoate | 1232167-07-5

• 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: tert-butyl 3-(methyl(phenyl)amino)-3-oxopropanoate
• 英文别名: tert-butyl 3-(N-methylanilino)-3-oxopropanoate
• CAS: 1232167-07-5
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: FJMKWDGRAKCNOE-UHFFFAOYSA-N

物化性质

• 沸点：
  342.0±25.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(methyl(phenyl)amino)-3-oxopropanoate 在 potassium tert-butylate 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 生成 tert-butyl 3-benzyl-1-methyl-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：

  N-甲基苯胺 在 三乙烯二胺 、 N-碘代丁二酰亚胺 、 水 、 palladium diacetate 、 silver nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 21.0h， 生成 tert-butyl 3-(methyl(phenyl)amino)-3-oxopropanoate
  参考文献：
  名称：

  Palladium-Catalyzed Alcoholysis of 3-Iodopropynamides: Selective Synthesis of Carbamoylacetates

  摘要：

  A novel and selective method for the synthesis of carbamoylacetates via the alcoholysis of 3-iodopropynamides has been developed. 3-Iodopropynamides react with alcohols in the presence of palladium(II) acetate and DABCO to afford the corresponding carbamoylacetates in moderate to good yields.

  DOI：

  10.1055/s-0034-1379104

文献信息

• Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids
  作者：Nivesh Kumar、Mrinal Kanti Das、Santanu Ghosh、Alakesh Bisai

  DOI：10.1039/c6cc10228j

  日期：——

  We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary...

  我们提出了一种有效的脱酰基烷基化策略，用于在假苄基位置上构筑各种带有2-碳吲哚的全碳季中心。季铵盐和季铵盐的种类繁多的产品
• Diels–Alder Reactions of α-Amido Acrylates with <i>N</i>-Cbz-1,2-dihydropyridine and Cyclopentadiene
  作者：Hossay Abas、Christopher S. Frampton、Alan C. Spivey

  DOI：10.1021/acs.joc.6b01684

  日期：2016.10.21

  Diels–Alder reactions of α-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene have been explored to investigate the factors influencing the endo/exo selectivity. For the dihydropyridine, steric factors allowed the diastereoselectivity to be modulated to favor either endo- or exo-ester adducts. For cyclopentadiene, the endo-ester adducts were favored regardless of steric perturbation, although

  研究了α-酰胺基丙烯酸酯与N -Cbz-1,2-二氢吡啶和环戊二烯的热Diels-Alder反应，以研究影响内/外选择性的因素。对于二氢吡啶，位阻因素所允许的非对映选择性进行调制以有利于任一内切或外切酯加合物。对于环戊二烯，将内-酯加合物，无论空间扰动的青睐，尽管催化由笨重的路易斯酸增加的比例外-酯加合物，在某些情况下。这些路易斯酸与二氢吡啶二烯不相容，因为它们引起其分解。
• Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation
  作者：Richard Taylor、David. Pugh、Johannes Klein、Alexis Perry

  DOI：10.1055/s-0029-1219392

  日期：2010.4

  A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

  介绍了一种将苯胺转化为 3-烷基-氧吲哚的新方法，其中先进行铜（II）介导的环化反应，然后再进行酸介导的脱羧基烷基化反应。报告了范围和局限性研究，以及结合了原位 N-脱保护的伸缩变体。
• 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.
• 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.