乙基3-羟基-1-吡咯烷羧酸酯 | 93591-91-4

• 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: 乙基3-羟基-1-吡咯烷羧酸酯
• 英文名称: ethyl 3-hydroxypyrrolidine-1-carboxylate
• 英文别名: 3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester；3-Hydroxy-pyrrolidin-1-carbonsaeure-aethylester；1-ethoxycarbonyl-3-pyrrolidinol
• CAS: 93591-91-4
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: AQCCUQNJHACLSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙基3-羟基-1-吡咯烷羧酸酯 在 K₂Cr₂O₄ 作用下， 生成 1-乙氧羰基吡咯烷-3-酮
  参考文献：
  名称：

  Evaluation of the eutomer of 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, {(+)-SYA 09}, a pyrrolidine analog of haloperidol

  摘要：

  Enantionteric separation of the racemic 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, a pyrrolidine analog of haloperidol, {(+/-)-SYA 09}, and subsequent binding studies revealed that most of the binding affinity at dopamine and serotonin receptors resides in the (+)-isomer {(+)-SYA 09} or the eutomer. Further pharmacological evaluation of the eutomer revealed that it has a higher affinity for the dopamine D4 (DAD4) receptor subtype (K-i = 3.6 nM) than for the DAD2 subtype (K-i = 51.1 nM) with a ratio of 14.2 (D2K(i)/D4K(i) ratio = 14.2). In an animal model of antipsychotic efficacy, the (+)-SYA 09 was efficacious with an ED50 value of 1.6 mg/kg, ip, and at twice this value, (+)-SYA 09 did not induce significant catalepsy in rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.057
• 作为产物：
  描述：

  1-乙氧羰基吡咯烷-3-酮 在 sodium tetrahydroborate 作用下， 生成 乙基3-羟基-1-吡咯烷羧酸酯
  参考文献：
  名称：

  饱和N-杂环酮的立体互补生物还原

  摘要：

  摘要 使用酮还原酶 READH 和 ChKRED20 分别以立体互补方式生产 (S)- 和 (R)- 醇，证明了几种饱和 N-杂环酮的不对称生物还原。该反应接受具有五元环、六元环或七元环的底物，并在使用 2-丙醇作为最终还原剂和助溶剂时表现出出色的立体选择性，在大多数情况下，两种对映异构体的 ee 均大于 99%。

  DOI：

  10.1016/j.procbio.2017.03.002

文献信息

• Ethyl Imidazole-1-carboxylate (EImC) as a Carbonylating Agent: Efficient Synthesis of Oxazolidin-2-ones from Amino Alcohols
  作者：S. Veeraswamy、K. Indrasena Reddy、R. Venkat Ragavan、Satyanarayana Yennam、A. Jayashree

  DOI：10.1246/cl.2013.109

  日期：2013.2.5

  Various substituted oxazolidin-2-ones were synthesized from the corresponding amino alcohols using ethyl imidazole-1-carboxylate (EImC). Highly substituted and sterically hindered amino alcohols and amino alcohols having a free hydroxy group were cyclized to oxazolidin-2-ones efficiently. This method is simple and produces oxazolidin-2-ones in very good yield.

  从相应的氨基醇合成了多种取代的噁唑烷-2-酮，使用了乙基咪唑-1-羧酸酯（EImC）。高度取代且空间位阻的氨基醇以及具有自由羟基的氨基醇均能高效环化为噁唑烷-2-酮。该方法简单，并能以非常好的产率生产噁唑烷-2-酮。
• [EN] COMPOUNDS AS MODULATORS OF BIS-PHOSPHOGLYCERATE MUTASE FOR THE TREATMENT OF SICKLE CELL DISEASE<br/>[FR] COMPOSÉS UTILISÉS EN TANT QUE MODULATEURS DE LA BISPHOSPHOGLYCÉRATE MUTASE POUR LE TRAITEMENT DE LA DRÉPANOCYTOSE
  申请人：GENZYME CORP

  公开号：WO2022056449A1

  公开（公告）日：2022-03-17

  Provided herein are compounds and compositions thereof for modulating bis-phosphoglycerate mutase (BPGM) for treating sickle cell disease.

  本文提供了一种用于调节双磷酸甘油酸酯酶（BPGM）治疗镰状细胞贫血的化合物和其组合物。
• Process for Production of Benzyloxypyrrolidine Derivative, and Process for Production of Hydrochloride Salt Powder of Optically Active Benzyloxypyrrolidine Derivative
  申请人：Morimoto Masao

  公开号：US20090093643A1

  公开（公告）日：2009-04-09

  Provided are: a process for production of a benzyloxypyrrolidine derivative in high yield and safety, and a process for production of a hydrochloride powder of a benzyloxypyrrolidine derivative in high yield and safety; the process for production of a benzyloxypyrrolidine derivative expressed by the general formula (2) [Chemical formula 2], in reacting a pyrrolidinol derivative represented by the general formula (1) [Chemical formula 1] with a benzyl halide derivative in the presence of an alkali metal hydroxide, wherein the reaction is carried out in either of the following conditions A or B; condition A: an aprotic polar solvent, and condition B: an aliphatic ether solvent containing a phase transfer catalyst:

  提供了一种高产率和安全性的苯甲氧吡咯烷衍生物的生产工艺，以及一种高产率和安全性的苯甲氧吡咯烷衍生物盐酸盐粉末的生产工艺。苯甲氧吡咯烷衍生物的生产工艺由化学式（2）[化学式2]表示，通过在碱金属氢氧化物存在下，用苯甲醇衍生物与苯甲基卤代物反应，反应条件为以下条件A或B之一：条件A为无极性极性溶剂，条件B为含有相转移催化剂的脂肪醚溶剂。
• Synthesis and evaluation of ligands for D2-like receptors: The role of common pharmacophoric groups
  作者：Donald M.N. Sikazwe、Nancy T. Nkansah、Ramazan Altundas、Xue Y. Zhu、Bryan L. Roth、Vincent Setola、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2008.12.054

  日期：2009.2

  Arylcycloalkylamines, such as phenyl piperidines and piperazines and their arylalkyl substituents, constitute pharmacophoric groups exemplified in several antipsychotic agents. A review of previous reports indicates that arylalkyl substituents can improve the potency and selectivity of the binding affinity at D-2-like receptors. In this paper, we explored the contributions of two key pharmacophoric groups, that is, 40-fluorobutyrophenones and 3-methyl-7-azaindoles, to the potency and selectivity of synthesized agents at D-2-like receptors. Preliminary observation of binding affinities indicates that there is little predictability of specific effects of the arylalkyl moieties but the composite structure is responsible for selectivity and potency at these receptors. Published by Elsevier Ltd.
• PROCESS FOR PRODUCTION OF BENZYLOXYPYRROLIDINE DERIVATIVE, AND PROCESS FOR PRODUCTION OF HYDROCHLORIDE SALT POWDER OF OPTICALLY ACTIVE BENZYLOXYPYRROLIDINE DERIVATIVE
  申请人：Toray Fine Chemicals Co., Ltd.

  公开号：EP1950198B1

  公开（公告）日：2014-08-06