N-(1,1-dimethylethoxy)methyl-2-pyrrolidinone | 144393-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(1,1-dimethylethoxy)methyl-2-pyrrolidinone
• 英文别名: 1-(tert-butoxymethyl)pyrrolidin-2-one；1-(tert-butoxymethyl)-2-pyrrolidone；1-[(2-Methylpropan-2-yl)oxymethyl]pyrrolidin-2-one
• CAS: 144393-27-1
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: QEYXTWKYGMTVOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  267.0±23.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  triethyloxonium fluoroborate 、 N-(1,1-dimethylethoxy)methyl-2-pyrrolidinone 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到2-ethoxy-N-(1,1-dimethylethoxy)methyl-2-pyrrolidiniminium tetrafluoroborate
  参考文献：
  名称：

  Zezza, Charles A.; Kwon, Tae Woo; Sheu, JennLine, Heterocycles, 1992, vol. 34, # 7, p. 1325 - 1342

  摘要：

  DOI：
• 作为产物：
  描述：

  (羟基甲基)-2-吡咯烷酮 在 氯化亚砜 作用下， 反应 25.0h， 生成 N-(1,1-dimethylethoxy)methyl-2-pyrrolidinone
  参考文献：
  名称：

  Zezza, Charles A.; Kwon, Tae Woo; Sheu, JennLine, Heterocycles, 1992, vol. 34, # 7, p. 1325 - 1342

  摘要：

  DOI：

文献信息

• Deoxygenation of tertiary and secondary alcohols ROH by thiol-catalysed radical-chain redox decomposition of derivatives ROCH2X to give RH and XCHO
  作者：Hai-Shan Dang、Brian P. Roberts

  DOI：10.1039/b202411j

  日期：2002.4.26

  electron-donating alkoxy, aryl or amido group, undergo thiol-catalysed radical-chain decomposition to give RH and XCHO. This reaction has been applied for the deoxygenation of representative tertiary and secondary alcohols ROH under metal-free conditions that require no stoichiometric co-reactant. Of the derivatives investigated, methoxymethyl (MOM) ethers and 1-alkoxymethylpyrrolidin-2-ones (PYRM ethers)

  ROCH 2 X类型的化合物，其中取代基X是供电子烷氧基，芳基 或酰胺基团，经历 硫醇催化自由基链 分解给RH和XCHO。该反应已用于代表性的叔胺和脱氧剂的脱氧。仲醇不含化学计量共反应物的无金属条件下的ROH。在研究的衍生物中，甲氧基甲基（MOM）醚 1-烷氧基甲基吡咯烷酮2-酮（PYRM醚）被证明是最普遍成功的方法，氧化还原分解产生RH的典型条件是在回流下加热。 辛烷 溶剂 在一个 过氧化物 发起人和 三叔-butoxysilanethiol[（Bu t O）3 SiSH]作为质子极性反转催化剂。在不存在以下条件的情况下，向RH的转化可以忽略不计硫醇。几种不同类型的叔醇包括甾体和碳水化合物实例在内的OH和MOM和PYRM醚均被脱氧，从而得到非常好的RH分离产率。尽管MOM和PYRM醚衍生自许多类型的仲醇 还提供了相对较高的相对湿度，MOM 醚 的 双丙酮D-葡萄糖 生成的3-脱氧糖收率不佳，相应的PYRM醚的收率仍然中等。
• Iron-Catalyzed Oxidative Coupling of Alkylamides with Arenes through Oxidation of Alkylamides Followed by Friedel−Crafts Alkylation
  作者：Eiji Shirakawa、Nanase Uchiyama、Tamio Hayashi

  DOI：10.1021/jo102217m

  日期：2011.1.7

  FeCL(3) in combination with t-BuOOt-Bu as an oxidant was found to be an efficient catalyst for oxidation of alkylamides to alpha-(tert-butoxy)alkylamides. FeCl(2) and CuCl showed, respectively, almost the same and slightly lower activities compared with FeCl(3) in the tert-butoxylation of N-phenylpyrrolidone (1a), whereas no tert-butoxylated product was obtained by use of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). FeCl(3) was found to be effective also as a catalyst for the Friedel-Crafts alkylation with thus obtained alpha-(tert-butoxy)alkylamides. The Friedel-Crafts alkylation proceeded smoothly also in the presence of a catalytic amount of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). In contrast, FeCl(2) and CuCl, which showed certain activity toward the tert-butoxylation, failed to promote the Friedel Crafts alkylation. Among the transition metal complexes thus far examined, only FeCl(3) showed high catalytic activities for both the oxidation and the Friedel-Crafts alkylation. The bifunctionality of FeCl(3) was utilized for the oxidative coupling of alkylamides with arenes through a tandem reaction consisting of oxidation of alkylamides to alpha-(tert-butoxy)alkylamides and the following Friedel-Crafts alkylation. The FeCl(3)-catalyzed oxidative coupling is applicable to a wide variety of alkylamides and arenes, though a combination of FeCl(3) with Fe(OTf)(3) was found to be effective for the reaction of arenes with low nucleophilicity. A Fe(II)-Fe(III) catalytic cycle is concerned with the tert-butoxylation, whereas a Fe(III) complex as a Lewis acid catalyzes the Friedel-Crafts alkylation.