4-Hydroxy-2-oxo-pyrrolidine-1-carboxylic acid benzyl ester

• 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: 4-Hydroxy-2-oxo-pyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: Benzyl 4-hydroxy-2-oxopyrrolidine-1-carboxylate
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: ABTKQISAPAZLRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-Hydroxy-2-oxo-pyrrolidine-1-carboxylic acid benzyl ester 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以51%的产率得到benzyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  N-取代的吡咯啉-2-酮的合成

  摘要：

  在关于合成小分子柯林类似物的研究中，当在4-二甲基氨基吡啶存在下用碳酸二叔丁酯处理1-苄氧基羰基-4-羟基-5-甲基吡咯烷丁-2-酮时，观察到了意外的脱水。该反应用于几种N-保护的吡咯烷-2-酮的立体定向合成。

  DOI：

  10.1016/0040-4039(95)02267-8

文献信息

• Process for preparing optically active 4-hydroxy-2-pyrrolidinone and n-substituted 4-hydroxy-2-pyrrolidinones by enzymatic hydroxylation
  申请人：——

  公开号：US20040009562A1

  公开（公告）日：2004-01-15

  This invention provides a process for the preparation of optically active 4-hydroxy-2-pyrrolidinone or N-substituted 4-hydroxy-2-pyrrolidinones, wherein an oxygen atom is inserted regio- and stereoselectively into the corresponding non-hydroxylated 2-pyrrolidinones, by using, as a biocatalyst, a microorganism having hydroxylation activity, or a host-organism having the gene(s) necessary for the hydroxylation enzymes derived from the said microorganism, or an enzyme having hydroxylation activity derived from the above microorganisms. The microorganism may be selected from the group consisting of microorganisms that degrade alkanes or cyclic hydrocarbons, microorganisms having alkane hydroxylase(s), or microorganisms that are able to oxidize hydrocarbons.

  本发明提供了一种制备光学活性4-羟基-2-吡咯烷酮或N-取代的4-羟基-2-吡咯烷酮的方法，其中将氧原子以区域和立体选择性插入相应的非羟基化2-吡咯烷酮中，使用具有羟化活性的微生物或具有来自所述微生物的羟化酶所必需的基因的宿主生物作为生物催化剂，或者使用来自上述微生物的羟化酶活性的酶。微生物可以从降解烷烃或环烃的微生物、具有烷烃羟化酶的微生物或能够氧化碳氢化合物的微生物中选择。
• Process for preparing optically active 4-hydroxy-2-pyrrolidinone and N-substituted 4-hydroxy-2-pyrrolidinones by enzymatic hydroxylation
  申请人：Eidgenössische Technische Hochschule Zürich

  公开号：EP1197561A1

  公开（公告）日：2002-04-17

  This invention provides a process for the preparation of optically active 4-hydroxy-2-pyrrolidinone or N-substituted 4-hydroxy-2-pyrrolidinones, wherein an oxygen atom is inserted regio- and stereoselectively into the corresponding non-hydroxylated 2-pyrrolidinones, by using, as a biocatalyst, a microorganism having hydroxylation activity, or a host-organism having the gene(s) necessary for the hydroxylation enzymes derived from the said microorganism, or an enzyme having hydroxylation activity derived from the above microorganisms. The microorganism may be selected from the group consisting of microorganisms that degrade alkanes or cyclic hydrocarbons, microorganisms having alkane hydroxylase(s), or microorganisms that are able to oxidize hydrocarbons.

  本发明提供了一种制备具有光学活性的 4-羟基-2-吡咯烷酮或 N-取代的 4-羟基-2-吡咯烷酮的工艺，其中氧原子可在相应的非羟基化 2-吡咯烷酮中进行区域和立体选择性插入、作为生物催化剂，使用具有羟基化活性的微生物，或具有羟基化酶所需基因的宿主生物，或从上述微生物中提取的具有羟基化活性的酶。所述微生物可选自降解烷烃或环烃的微生物、具有烷烃羟化酶的微生物或能够氧化烃的微生物。
• PROCESS FOR PREPARING OPTICALLY ACTIVE 4-HYDROXY-2-PYRROLIDINONE AND N-SUBSTITUTED 4-HYDROXY-2-PYRROLIDINONES BY ENZYMATIC HYDROXYLATION
  申请人：Eidgenössiche Technische Hochschule Zürich

  公开号：EP1325146B1

  公开（公告）日：2005-12-14
• [EN] PROCESS FOR PREPARING OPTICALLY ACTIVE 4-HYDROXY-2-PYRROLIDINONE AND N-SUBSTITUTED 4-HYDROXY-2-PYRROLIDINONES BY ENZYMATIC HYDROXYLATION<br/>[FR] PROCEDE DE PREPARATION DE 4-HYDROXY-2-PYRROLIDINONE ET DE 4-HYDROXY-2-PYRROLIDINONES N-SUBSTITUEES OPTIQUEMENT ACTIVES PAR HYDROXYLATION ENZYMATIQUE
  申请人：EIDGENOESSICHE TECH HOCHSCHULE

  公开号：WO2002031174A2

  公开（公告）日：2002-04-18

  This invention provides a process for the preparation of optically active 4-hydroxy-2-pyrrolidinone or N-substituted 4-hydroxy-2-pyrrolidinones, wherein an oxygen atom is inserted regio- and stereoselectively into the corresponding non-hydroxylated 2-pyrrolidinones, by using, as a biocatalyst, a microorganism having hydroxylation activity, or a host-organism having the gene(s) necessary for the hydroxylation enzymes derived from the said microorganism, or an enzyme having hydroxylation activity derived from the above microorganisms. The microorganism may be selected from the group consisting of microorganisms that degrade alkanes or cyclic hydrocarbons, microorganisms having alkane hydroxylase(s), or microorganisms that are able to oxidize hydrocarbons.
• Synthesis of N-substituted pyrrolin-2-ones
  作者：Ralph-Heiko Mattern

  DOI：10.1016/0040-4039(95)02267-8

  日期：1996.1

  During studies towards the synthesis of microcolin analogues, an unexpected dehydration was observed when 1-benzyloxycarbonyl-4-hydroxy-5-methylpyrrolidin-2-one was treated with di-tert-butyl dicarbonate in the presence of 4-dimethylaminopyridine. This reaction was used for the stereospecific synthesis of several N-protected pyrrolin-2-ones.

  在关于合成小分子柯林类似物的研究中，当在4-二甲基氨基吡啶存在下用碳酸二叔丁酯处理1-苄氧基羰基-4-羟基-5-甲基吡咯烷丁-2-酮时，观察到了意外的脱水。该反应用于几种N-保护的吡咯烷-2-酮的立体定向合成。