(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-isobutyl-4-methyl-2,5-dihydro-1H-pyrrole | 374937-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-isobutyl-4-methyl-2,5-dihydro-1H-pyrrole
• 英文别名: tert-butyl-dimethyl-[[(5R)-3-methyl-5-(2-methylpropyl)-1,2-dihydropyrrol-5-yl]methoxy]silane
• CAS: 374937-21-0
• 化学式: C₁₆H₃₃NOSi
• 分子量: 283.53
• InChiKey: QOWQTOCVWCPSGM-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-isobutyl-4-methyl-2,5-dihydro-1H-pyrrole 在 sodium hypochlorite 、 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-1-chloro-5-isobutyl-3-methyl-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  2,2,4-三取代的3-吡咯啉的氧化研究

  摘要：

  作为针对乳酸菌素全合成的研究的一部分，我们已经开发出一种可靠且环境可接受的方法，可将2,2,4-三取代的3-吡咯啉氧化为相应的3-吡咯啉-2-酮。检查了几种方案，分为两步（i）TPAP / NMO；（ii）发现次氯酸钠的烯丙基氧化是最令人满意的。3-吡咯啉的催化氧化以高收率得到相应的环状亚胺，随后用NaOCl氧化得到N-氯-3-吡咯啉-2-一。所述Ñ通过简单的酸处理除去氯取代基。

  DOI：

  10.1016/s0040-4039(02)00285-x
• 作为产物：
  描述：

  (3-bromo-2-methyl-allyl)-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-butyl]-amine 在 双(三甲基硅烷基)氨基钾 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 以53%的产率得到(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-isobutyl-4-methyl-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  A Convenient Method for 3-Pyrroline Synthesis

  摘要：

  [GRAPHICS]The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylldene carbene CH-Insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary stereocenters is a relatively facile process. The insertion reaction occurs with > 95% retention of stereochemistry, but the presence of protecting groups on nitrogen is generally deleterious to the cyclization process.

  DOI：

  10.1021/ol016603c

文献信息

• A Convenient Method for 3-Pyrroline Synthesis
  作者：Martin P. Green、Jeremy C. Prodger、Alexandra E. Sherlock、Christopher J. Hayes

  DOI：10.1021/ol016603c

  日期：2001.10.1

  [GRAPHICS]The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylldene carbene CH-Insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary stereocenters is a relatively facile process. The insertion reaction occurs with > 95% retention of stereochemistry, but the presence of protecting groups on nitrogen is generally deleterious to the cyclization process.
• Studies on the oxidation of 2,2,4-trisubstituted 3-pyrrolines
  作者：Martin P Green、Jeremy C Prodger、Christopher J Hayes

  DOI：10.1016/s0040-4039(02)00285-x

  日期：2002.4

  As part of our studies directed towards a total synthesis of lactacystin, we have developed a reliable and environmentally acceptable method to oxidise 2,2,4-trisubstituted 3-pyrrolines to the corresponding 3-pyrrolin-2-ones. Several protocols were examined and the two-step (i) TPAP/NMO; (ii) sodium hypochlorite allylic oxidation was found to be the most satisfactory. Catalytic oxidation of the 3-pyrroline

  作为针对乳酸菌素全合成的研究的一部分，我们已经开发出一种可靠且环境可接受的方法，可将2,2,4-三取代的3-吡咯啉氧化为相应的3-吡咯啉-2-酮。检查了几种方案，分为两步（i）TPAP / NMO；（ii）发现次氯酸钠的烯丙基氧化是最令人满意的。3-吡咯啉的催化氧化以高收率得到相应的环状亚胺，随后用NaOCl氧化得到N-氯-3-吡咯啉-2-一。所述Ñ通过简单的酸处理除去氯取代基。