tert-butyl 2-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate | 1011716-08-7

• 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: tert-butyl 2-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl 2-hydroxy-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 1011716-08-7
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: ZWLKWISWXLHFDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5(RS)-hydroxy-3-pyrrolin-2-one
  参考文献：
  名称：

  2-甲硅烷氧基吡咯的二甲基二环氧乙烷氧化：5-羟基-3-吡咯啉-2-酮的有效区域控制合成

  摘要：

  报道了一种合成 5-羟基-3-吡咯啉-2-酮的新方法。N-Boc-3-pyrrolin-2-ones 转化为 2-triisopropylsilyloxypyrroles 并随后用二甲基二环氧乙烷氧化以高产率提供相应的 N-Boc-5-hydroxy-3-pyrrolin-2-ones。

  DOI：

  10.1055/s-2007-992376
• 作为产物：
  描述：

  2-furoyl azide 在 水 、 碘 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 tert-butyl 2-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation

  摘要：

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.011

文献信息

• Synthesis of 2,4-Disubstituted Pyrroles by Rearrangements of 2-Furanyl Carbamates
  作者：Sezgin Kiren、Xuechuan Hong、Carolyn A. Leverett、Albert Padwa

  DOI：10.1021/ol900059e

  日期：2009.3.19

  2,4-Disubstituted pyrroles were synthesized by an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with different alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine.

  通过呋喃基氨基甲酸酯的氧化重排，然后使所得的5-甲氧基吡咯-2（5 H）-one与不同的烷基锂酸酯顺序反应，合成了2,4-二取代的吡咯。该方法的最后步骤涉及将开环的1-甲氧基-5-氧戊基氨基甲酸酯与伯胺一起加热。
• Oxidative rearrangement of 2-furylcarbamates with dimethyldioxirane: a high-yielding preparation of 5-hydroxypyrrol-2(5H)-ones
  作者：John Boukouvalas、Richard P. Loach、Etienne Ouellet

  DOI：10.1016/j.tetlet.2011.07.084

  日期：2011.9

  A mild, general and efficient method for the oxidative rearrangement of 2-furylcarbamates to N-Boc-5-hydroxypyrrol-2(5H)-ones is reported. The feasibility of removing the Boc group from the products was demonstrated by the synthesis of two hitherto unknown 5-aryl-5-hydroxypyrrol-2(5H)-ones. (C) 2011 Elsevier Ltd. All rights reserved.
• MONOACYLGLYCEROL LIPASE MODULATORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20210253565A1

  公开（公告）日：2021-08-19

  3.1.0 and 4.1.0 Azabicycle compounds of Formula (I), pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with MGL modulation, such as those associated with pain, psychiatric disorders, neurological disorders (including, but not limited to major depressive disorder, treatment resistant depression, anxious depression, bipolar disorder), cancers and eye conditions. wherein X, Y, R 1 , R 2a , and R 2b are defined herein.
• A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation
  作者：Sezgin Kiren、Xuechuan Hong、Carolyn A. Leverett、Albert Padwa

  DOI：10.1016/j.tet.2009.03.011

  日期：2009.8

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.
• Dimethyldioxirane Oxidation of 2-Silyloxypyrroles: An Efficient Regiocontrolled Synthesis of 5-Hydroxy-3-pyrrolin-2-ones
  作者：John Boukouvalas、Yufang Xiao、Yun-Xing Cheng、Richard Loach

  DOI：10.1055/s-2007-992376

  日期：——

  A new method for the synthesis of 5-hydroxy-3-pyrrolin-2-ones is reported. Conversion of N-Boc-3-pyrrolin-2-ones into 2-triisopropylsilyloxypyrroles and ensuing oxidation with dimethyldioxirane provides the corresponding N-Boc-5-hydroxy-3-pyrrolin-2-ones in high yields.

  报道了一种合成 5-羟基-3-吡咯啉-2-酮的新方法。N-Boc-3-pyrrolin-2-ones 转化为 2-triisopropylsilyloxypyrroles 并随后用二甲基二环氧乙烷氧化以高产率提供相应的 N-Boc-5-hydroxy-3-pyrrolin-2-ones。