(R)-5-dimethylamminomethyl-2-oxazolidinone | 1373346-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-5-dimethylamminomethyl-2-oxazolidinone
• 英文别名: (5R)-5-[(dimethylamino)methyl]-1,3-oxazolidin-2-one
• CAS: 1373346-22-5
• 化学式: C₆H₁₂N₂O₂
• 分子量: 144.173
• InChiKey: LIUNIAJFCDDQCI-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-dimethylamminomethyl-2-oxazolidinone 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 C₈H₁₇N₂O₂⁽¹⁺⁾*I^(1-)
  参考文献：
  名称：

  乙酰胆碱氨基甲酰基类似物的设计，合成和结合亲和力

  摘要：

  测试了在氨基甲酸酯部分或阳离子头或两者上环化的一系列乙酰胆碱氨基甲酰基类似物对毒蕈碱和神经元烟碱样受体（nAChRs）的结合亲和力。虽然没有毒蕈碱亲和力发现，亚微摩尔ķ我值，类似于卡巴胆碱，物在α测定4 β 2个nAChRs的5二甲基氨基甲基和5- trimethylammoniomethyl甲基-2-恶唑烷酮，对映体2和2a中，以及用于（S）-N-甲基脯氨醇氨基甲酸酯（S）-3。2和2a和的恶唑烷酮氮的甲基化（S）-3的N-甲基脯氨醇氮以及甚至更多的环状氨基甲酸酯亚结构（恶唑烷酮）与环状阳离子头（N-甲基吡咯烷）的杂交显着降低了烟碱亲和力。对接结果与SAR分析一致，突出了（R）-2a和（S）-3的相互作用能力以及环内氮甲基化和双环化的负面影响。

  DOI：

  10.1016/j.bmcl.2013.09.023
• 作为产物：
  描述：

  (R)-carnitinchloramide chloride 在 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 (R)-5-dimethylamminomethyl-2-oxazolidinone
  参考文献：
  名称：

  From carnitinamide to 5-aminomethyl-2-oxazolidinones

  摘要：

  Carnitinamide chloride, an immediate synthetic precursor of carnitine, was chlorinated at the amide nitrogen. The resultant carnitinechloramide chloride, when treated with a base, revealed that the first-formed isolable and characterisable carnitinechloramide inner salt undergoes solid state conversion into 5-trimethylammoniomethyl-2-oxazolidinone chloride via Hoffmann rearrangement and intramolecular cyclization of the beta-hydroxyisocyanate. The trimethylaminomethyl substituent at C-5 of the 2-oxazolidinone was converted into a dimethylaminomethyl group by microwave-assisted demethylation in DMF and then into a methylaminomethyl group by decomposition of the alpha-chloroethyl carbamate obtained by treatment with alpha-chloroethyl chloroformate. This sequence of reactions was then applied to both (S)- and (R)-carnitinamide chloride without any racemization to yield both enantiomers of 5-aminomethyl-2-oxazolidinones that are mono-, di- and tri-methylated at the exocyclic nitrogen. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.006

文献信息

• Design, synthesis and binding affinity of acetylcholine carbamoyl analogues
  作者：Cristiano Bolchi、Ermanno Valoti、Matteo Binda、Francesca Fasoli、Rossana Ferrara、Laura Fumagalli、Cecilia Gotti、Rosanna Matucci、Giulio Vistoli、Marco Pallavicini

  DOI：10.1016/j.bmcl.2013.09.023

  日期：2013.12

  A series of acetylcholine carbamoyl analogues, cyclised at the carbamate moiety or at the cationic head or at both, were tested for binding affinity at muscarinic and neuronal nicotinic receptors (nAChRs). While no muscarinic affinity was found, submicromolar Ki values, similar to that of carbachol, were measured at α4β2 nAChRs for the enantiomers of 5-dimethylaminomethyl- and 5-trimethylammoniome

  测试了在氨基甲酸酯部分或阳离子头或两者上环化的一系列乙酰胆碱氨基甲酰基类似物对毒蕈碱和神经元烟碱样受体（nAChRs）的结合亲和力。虽然没有毒蕈碱亲和力发现，亚微摩尔ķ我值，类似于卡巴胆碱，物在α测定4 β 2个nAChRs的5二甲基氨基甲基和5- trimethylammoniomethyl甲基-2-恶唑烷酮，对映体2和2a中，以及用于（S）-N-甲基脯氨醇氨基甲酸酯（S）-3。2和2a和的恶唑烷酮氮的甲基化（S）-3的N-甲基脯氨醇氮以及甚至更多的环状氨基甲酸酯亚结构（恶唑烷酮）与环状阳离子头（N-甲基吡咯烷）的杂交显着降低了烟碱亲和力。对接结果与SAR分析一致，突出了（R）-2a和（S）-3的相互作用能力以及环内氮甲基化和双环化的负面影响。
• From carnitinamide to 5-aminomethyl-2-oxazolidinones
  作者：Cristiano Bolchi、Marco Pallavicini、Matteo Binda、Laura Fumagalli、Ermanno Valoti

  DOI：10.1016/j.tetasy.2012.02.006

  日期：2012.2

  Carnitinamide chloride, an immediate synthetic precursor of carnitine, was chlorinated at the amide nitrogen. The resultant carnitinechloramide chloride, when treated with a base, revealed that the first-formed isolable and characterisable carnitinechloramide inner salt undergoes solid state conversion into 5-trimethylammoniomethyl-2-oxazolidinone chloride via Hoffmann rearrangement and intramolecular cyclization of the beta-hydroxyisocyanate. The trimethylaminomethyl substituent at C-5 of the 2-oxazolidinone was converted into a dimethylaminomethyl group by microwave-assisted demethylation in DMF and then into a methylaminomethyl group by decomposition of the alpha-chloroethyl carbamate obtained by treatment with alpha-chloroethyl chloroformate. This sequence of reactions was then applied to both (S)- and (R)-carnitinamide chloride without any racemization to yield both enantiomers of 5-aminomethyl-2-oxazolidinones that are mono-, di- and tri-methylated at the exocyclic nitrogen. (C) 2012 Elsevier Ltd. All rights reserved.