(4S)-4-羟基-2-氧代-1-吡咯烷羧酸叔丁酯 | 320343-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (4S)-4-羟基-2-氧代-1-吡咯烷羧酸叔丁酯
• 中文别名: S-1-BOC-2-氧代-4-羟基吡咯烷
• 英文名称: (S)-N-tert-butoxycarbonyl-4-hydroxy-pyrrolidin-2-one
• 英文别名: (S)-1-Boc-4-Hydroxy-2-pyrrolidinone；tert-butyl (4S)-4-hydroxy-2-oxopyrrolidine-1-carboxylate
• CAS: 320343-58-6
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: GUVYWSACSIYEDN-LURJTMIESA-N

物化性质

• 沸点：
  360.6±35.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 、 (4S)-4-羟基-2-氧代-1-吡咯烷羧酸叔丁酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以57%的产率得到tert-butyl (S)-2-oxo-4-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  具有抗炎活性的天然产物人参皂苷类似物的合成

  摘要：

  人参皂苷是来自草药的主要生物活性成分，具有广泛的药理功能。Goodyeroside A 是kinsenoside 的一种差向异构体，仍然很少被探索。在本报告中，我们化学合成了人参皂苷、Goodyeroside A 及其类似物，具有聚糖变异、手性中心的手性反转以及内酰胺对内酯的生物等排置换。在这些化合物中，goodyeroside A 及其甘露糖基对应物表现出优异的抗炎功效。此外，还发现枸杞苷 A 通过抑制 NF-κB 信号通路有效抑制炎症。还探索了构效关系，以进一步开发更有前途的人参皂苷类似物作为候选药物。

  DOI：

  10.1016/j.bmc.2020.115854
• 作为产物：
  描述：

  tert-butyl (S)-4-((tert-butyldimethylsilyl)oxy)-2-oxopyrrolidine-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以77%的产率得到(4S)-4-羟基-2-氧代-1-吡咯烷羧酸叔丁酯
  参考文献：
  名称：

  具有抗炎活性的天然产物人参皂苷类似物的合成

  摘要：

  人参皂苷是来自草药的主要生物活性成分，具有广泛的药理功能。Goodyeroside A 是kinsenoside 的一种差向异构体，仍然很少被探索。在本报告中，我们化学合成了人参皂苷、Goodyeroside A 及其类似物，具有聚糖变异、手性中心的手性反转以及内酰胺对内酯的生物等排置换。在这些化合物中，goodyeroside A 及其甘露糖基对应物表现出优异的抗炎功效。此外，还发现枸杞苷 A 通过抑制 NF-κB 信号通路有效抑制炎症。还探索了构效关系，以进一步开发更有前途的人参皂苷类似物作为候选药物。

  DOI：

  10.1016/j.bmc.2020.115854

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。
• Preparation of (<i>S</i>)-<i>N</i>-Substituted 4-Hydroxy-pyrrolidin-2-ones by Regio- and Stereoselective Hydroxylation with <i>Sphingomonas </i>sp. HXN-200
  作者：Dongliang Chang、Bernard Witholt、Zhi Li

  DOI：10.1021/ol006735q

  日期：2000.11.1

  Enantiopure (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones have been prepared for the first time by regio- and stereoselective hydroxylation of the corresponding pyrrolidin-2-ones by use of a biocatalyst. Hydroxylation of 6 and 8 with Sphingomonas sp. HXN-200 afforded 68% of (S)-7 in >99.9% ee and 46% of (S)-9 in 92% ee, respectively. Simple crystallization increased the ee of (S)-9 to 99.9% in 82% yield.
• 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.