3-(叔丁基氨基)-3-氧代丙酸乙酯 | 17797-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(叔丁基氨基)-3-氧代丙酸乙酯
• 英文名称: ethyl 3-(tert-butylamino)-3-oxopropanoate
• CAS: 17797-87-4
• 化学式: C₉H₁₇NO₃
• mdl: MFCD24392303
• 分子量: 187.239
• InChiKey: QADAZNVHNJFDTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(叔丁基氨基)-3-氧代丙酸乙酯 在 溴 、 potassium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  一种噻吗洛尔杂质的制备方法

  摘要：

  本发明公开了一种噻吗洛尔杂质的制备方法，属于噻吗洛尔杂质合成技术领域，以3‑卤代‑4‑吗啉基‑1,2,5‑噻二唑为起始原料经碱性水解和酸处理制得中间体M1，以丙二酸单乙酯钾盐和叔丁胺经缩合反应制得中间体M2，中间体M2和液溴经取代反应制得中间体M3，中间体M3再与中间体M1经亲核取代反应制得中间体M4，中间体M4经还原反应和碱性水解制得目标产物。该方法合成路线合理、原料易得、操作简单易行，具有收率高和纯度高的特点。本发明制备得到的可作为对照品供噻吗洛尔质量研究中杂质的定性定量研究，控制原料药有关物质的含量，保证原料药的质量。

  公开号：

  CN112920138B
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 在 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 336.0h， 生成 3-(叔丁基氨基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  Transacylation of α-Aryl-β-keto Esters

  摘要：

  The acyl group of an alpha-aryl-beta-keto ester was readily transferred to N-, O-, and S-nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, which enabled the chemoselective monoacylation of diamines and amino alcohols without any modifications such as protection.

  DOI：

  10.1021/jo0344642

文献信息

• Anodic oxidation of di-tert-butyl disulfide: a facile method for the preparation of N-tert-butylamides
  作者：Driss Elothmani、Quang Tho Do、Jacques Simonet、Georges Le Guillanton

  DOI：10.1039/c39930000715

  日期：——

  The electrochemical oxidation of di-tert-butyl disulfide is shown to correspond to a one electron process; at 1.3 V, one carbon–sulfur bond is cleaved yielding two intermediate special : the tret-butyl cation and the radical ButS–S˙; a Ritter reaction occurs with the cation when the sovent is a nitrile and the cation dimerizes in to a tetrasulfide; at a more positive potential (1.9V) the two carbon–sulfur bonds are cleaved giving But+ and sulfur.

  电化学氧化二叔丁基二硫化物表明其对应于一个单电子过程；在1.3 V时，一个碳-硫键断裂，生成两个中间体：叔丁基碳正离子和自由基ButS–S˙；当溶剂为腈时，碳正离子会发生Ritter反应并二聚成四硫化物；在更正的电位（1.9V）下，两个碳-硫键断裂，产生正丁基和硫。
• Polyvinylpolypyrrolidone-Supported Boron Trifluoride; Highly Efficient Catalyst for the Synthesis of<i>N</i>-<i>tert</i>-Butyl Amides
  作者：Masoud Mokhtary、Faranak Najafizadeh

  DOI：10.1155/2012/632574

  日期：——

  Highly efficient method for the preparation ofN-tert-butyl amides by reaction of nitriles withtert-butyl acetate is described using polyvinylpolypyrrolidone-supported boron trifluoride (PVPP-BF₃) at 70°C in good to excellent yields. Selective amidation of benzonitrile in the presence of acetonitrile was also achieved. polyvinylpolypyrrolidone-boron trifluoride complex shows non-corrosive and stable solid catalyst elevated Lewis acid property.

  通过在70°C下使用聚乙烯吡咯烷酮支持的三氟化硼（PVPP-BF3），以良好至优异的产率描述了一种高效的方法，通过腈与叔丁基乙酸叔丁酯反应制备N-叔丁基酰胺。在乙腈存在下实现了对苯腈的选择性酰胺化。聚乙烯吡咯烷酮-三氟化硼复合物表现出非腐蚀性和稳定的固体催化剂，具有升高的Lewis酸性能。
• Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups
  作者：Yumi Nakaike、Daisuke Hayashi、Nagatoshi Nishiwaki、Yoshito Tobe、Masahiro Ariga

  DOI：10.1039/b815306j

  日期：——

  therefore, serve as C3N1 building blocks having a nitro group to afford nitropyridones and aminonitropyridines with a functional group at the 3-position. Upon treatment with malonic acid derivatives or β-keto esters, nitropyridones were obtained, whereas reactions with functionalized acetonitriles afford aminonitropyridines, via a formal transfer of an alkyl group from the ring nitrogen to the imino group

  β-甲酰基-β-亚硝胺1同时具有亲电甲酰基和亲核氨基，因此，作为具有硝基的C 3 N 1结构单元，可以提供在3-位具有官能团的硝基吡啶酮和氨基硝基吡啶。经治疗丙二酸可以得到硝基吡啶酮衍生物或β-酮酯，而与官能化乙腈的反应则是通过烷基从环氮到亚氨基的正式转移而得到氨基硝基吡啶。这些程序提供了制备具有硝基的杂环的实用方法。
• SO₄²⁻/Ce<i>_x</i>Zr₁₋<i>_x</i>O₂-catalyzed Synthesis of <i>N</i>-<i>tert</i>-Butylamides from Various Nitriles under Solvent-free Conditions
  作者：Sandeep S. Kahandal、Sandip R. Kale、Shamrao T. Disale、Radha V. Jayaram

  DOI：10.1246/cl.2012.738

  日期：2012.7.5

  The synthesis of N-tert-butylamides using SO42−/CexZr1−xO2 catalysts under solvent-free conditions is reported. The methodology has several advantages such as reusability of the catalyst, solvent-free conditions, easy workup, and comparable yield of N-tert-butylamides. A variety of aliphatic, aromatic, and acid-sensitive substrates give high to moderate yields of the corresponding N-tert-butylamides. Surface acidities of the catalysts were correlated with the results obtained. To the best of our knowledge, this is the first report of a modified Ritter reaction on SO42−/CexZr1−xO2 using tert-butyl acetate as carbocationic source.

  报道了在无溶剂条件下，利用SO42−/CexZr1−xO2催化剂合成N-叔丁基酰胺的方法。该方法具有多个优点，如催化剂可重复使用、无溶剂条件、简单的后处理过程，以及比较相似的N-叔丁基酰胺的产率。多种脂肪族、芳香族及酸敏感底物均能获得高至中等的相应N-叔丁基酰胺的产率。催化剂的表面酸度与所得结果相关联。据我们所知，这是首次报道在SO42−/CexZr1−xO2催化下，使用叔丁醇乙酸酯作为正电荷源进行改进型Ritter反应。
• Tunable Copper-Catalyzed Reaction of C₆₀ with 2-Ethoxycarbonylacetamides and Subsequent BF₃·Et₂O-Mediated Isomerization of the Generated Dihydrofuran-Fused Fullerenes to Fulleropyrrolidinones
  作者：Qiaoqiao Teng、Yi-Chen Tan、Chun-Bao Miao、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1021/acs.joc.8b02547

  日期：2018.12.21

  copper-catalyzed reaction of C60 with 2-ethoxycarbonylacetamides using air as the oxidant has been explored, which selectively affords methanofullerenes (2) and dihydrofuran-fused fullerenes (3) under the CuI/DMAP and CuCl/NMI catalytic systems, respectively. Furthermore, the generated dihydrofuran-fused fullerenes could be transformed to fulleropyrrolidinones (4 and 5) upon treatment with BF3·Et2O.

  已经研究了使用空气作为氧化剂的C 60与2-乙氧基羰基乙酰胺的可调谐铜催化反应，该反应分别在CuI / DMAP和CuCl / NMI催化体系下分别提供了甲基富勒烯（2）和二氢呋喃稠合的富勒烯（3）。 。此外，在用BF 3 ·Et 2 O处理后，生成的二氢呋喃稠合的富勒烯可以转化为全吡咯烷酮（4和5）。