3-isopropyl-5-<((methanesulfonyl)oxy)methyl>oxazolidin-2-one | 99726-39-3

• 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: 3-isopropyl-5-<((methanesulfonyl)oxy)methyl>oxazolidin-2-one
• 英文别名: (3-isopropyl-2-oxooxazolidin-5-yl)methyl methanesulfonate；(2-oxo-3-propan-2-yl-1,3-oxazolidin-5-yl)methyl methanesulfonate
• CAS: 99726-39-3
• 化学式: C₈H₁₅NO₅S
• 分子量: 237.277
• InChiKey: KHAVBYUNOCYTST-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±18.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-isopropyl-5-<((methanesulfonyl)oxy)methyl>oxazolidin-2-one 在 氢氧化钾 作用下， 以 苯 为溶剂， 反应 48.0h， 生成 普萘洛尔
  参考文献：
  名称：

  Oxazolidin-2-ones from allylic amines by means of iodine and carbonate anion on polymeric support. A convenient synthesis of (.+-.)-propranolol

  摘要：

  DOI：

  10.1021/jo00355a023
• 作为产物：
  描述：

  (R,S)-5-acetoxymethyl-3-isopropyl-oxazolidin-2-one 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 3-isopropyl-5-<((methanesulfonyl)oxy)methyl>oxazolidin-2-one
  参考文献：
  名称：

  Oxazolidin-2-ones from allylic amines by means of iodine and carbonate anion on polymeric support. A convenient synthesis of (.+-.)-propranolol

  摘要：

  DOI：

  10.1021/jo00355a023

文献信息

• Bioisosteric Replacement and Related Analogs in the Design, Synthesis and Evaluation of Ligands for Muscarinic Acetylcholine Receptors
  作者：Richie Bhandare、Daniel Canney

  DOI：10.2174/15734064113096660043

  日期：2014.4

  Previous structure-activity relationship studies involving a series of lactone-based muscarinic ligands identified a lead compound containing a diphenylmethylpiperazine moiety (4; IC50 = 340 nM). The purpose of the present work is to investigate 1,3-benzodioxoles, 4,4-diethyl substituted tetrahydrofurans, 5-substituted oxazolidinones and chromones as bioisosteric replacements for the lactone ring in a novel series of muscarinic ligands. The approach provided compounds with improved % inhibition values and identified a non-selective muscarinic ligand with an IC50 value of 280 nM. The structure-activity relationship for this new series will be discussed. Selected compounds were evaluated in preliminary assays for subtype selectivity and were found to be non-selective.

  之前关于一系列基于内酯的毒蕈碱配体的结构-活性关系研究中，确定了一种含有二苯甲基哌嗪基团的领先化合物（4；IC50 = 340 nM）。本研究的目的是探讨1,3-苯并二氧杂环、4,4-二乙基取代的四氢呋喃、5-取代的噁唑烷酮和色烯作为新系列毒蕈碱配体中内酯环的生物等效替代物。该方法提供了具有改善的抑制率值的化合物，并识别出一种非选择性的毒蕈碱配体，其IC50值为280 nM。将讨论这一新系列的结构-活性关系。选定的化合物在初步实验中进行亚型选择性评估，结果发现它们是非选择性的。
• [EN] DISUBSTITUTED OXAZOLIDIN-2-ONES 5-HYDROXYTRYPTAMINE RECEPTOR 2B ACTIVITY MODULATORS<br/>[FR] OXAZOLIDIN-2-ONES DISUBSTITUÉES, MODULATEURS DE L'ACTIVITÉ DU RÉCEPTEUR 2B DE 5-HYDROXYTRYPTAMINE
  申请人：UNIV TEMPLE

  公开号：WO2014085413A1

  公开（公告）日：2014-06-05

  Pharmaceutical compositions of the invention comprise disubstituted oxazolidin-2-ones derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 2b activity.

  本发明的药物组合物包括二取代氧唑啉-2-酮衍生物，具有疾病修饰作用，用于治疗与5-羟色胺受体2b活性失调相关的疾病。
• Method of preparing a heterocyclic intermediate for the production of optically active aryloxysubstituted vicinal aminoalcohols
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0647633A1

  公开（公告）日：1995-04-12

  The invention relates to a method of preparing a heterocyclic intermediate of the general formula wherein    X is a carbonyl group, a thiocarbonyl group, a (C₁-C₁₀)(ar)alkylidene group or a dihydrocarbylsilyl group,    R is a straight or branched (C₁-C₁₀)alkyl group, optionally substituted with halogen, hydroxy, (C₁-C₄)alkoxy or protected hydroxy, or a phenyl(C₁-C₃)alkyl or heteroaryl(C₁-C₃)alkyl group, which groups are optionally substituted with 1-3 substituents, selected from the group consisting of hydroxy, (C₅-C₁₂)cycloalkyl, amino, nitro, halogen, cyano, alkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylsulphonylamino, alkylsulphonyl, alkylcarbonyl, and alkyl, wherein the alkyl groups have 1-5 carbon atoms, and which intermediate has either the R or the S configuration, by subjecting an optically active cyanohydrin of the general formula to a reduction-transimination-reduction sequence, using R - NH₂ as the primary amine, followed by a cyclization reaction and, finally, by an ozonolysis-reduction sequence.

  本发明涉及一种制备杂环中间体的方法，其通式如下：其中X为羰基，硫代羰基，(C₁-C₁₀)(芳)烷基亚甲基或二氢基碳基硅基，R为直链或支链(C₁-C₁₀)烷基，可选用卤素、羟基、(C₁-C₄)烷氧基或保护羟基进行取代，或苯基(C₁-C₃)烷基或杂环芳基(C₁-C₃)烷基，这些基团可选用1-3个取代基进行取代，所述取代基选自羟基、(C₅-C₁₂)环烷基、氨基、硝基、卤素、氰基、烷氧基、烷基羰氧基、烷基羰基氨基、烷基磺酰胺基、烷基磺酰基、烷基羰基和烷基，其中烷基含有1-5个碳原子，该中间体具有R或S构型，通过将手性氰醇通式的还原-转移-还原序列，使用R-NH₂作为主要胺，然后进行环化反应，最后进行臭氧化-还原序列。
• DISUBSTITUTED OXAZOLIDIN-2-ONES 5-HYDROXYTRYPTAMINE RECEPTOR 2B ACTIVITY MODULATORS
  申请人：TEMPLE UNIVERSITY - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：US20150291539A1

  公开（公告）日：2015-10-15

  Pharmaceutical compositions of the invention comprise disubstituted oxazolidin-2-ones derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 2b activity.

  本发明的制药组合物包括二取代噁唑烷-2-酮衍生物，具有改变疾病作用，用于治疗与5-羟色胺受体2b活性失调相关的疾病。
• Method of preparing a heterocyclic intermediate for the production of optically active aryloxy-substituted vicinal aminoalcohols
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0647634A1

  公开（公告）日：1995-04-12

  The invention relates to a method of preparing a heterocyclic intermediate of the general formula wherein    X is a carbonyl group, a thiocarbonyl group, a (C₁-C₁₀)(ar)alkylidene group or a dihydrocarbylsilyl group,    R is a straight or branched (C₁-C₁₀)alkyl group, optionally substituted with halogen, hydroxy, (C₁-C₄) alkoxy or protected hydroxy, or a phenyl(C₁-C₃)alkyl or heteroaryl(C₁-C₃)alkyl group, which groups are optionally substituted with 1-3 substituents, selected from the group consisting of hydroxy, (C₅-C₁₂)cycloalkyl, amino, nitro, halogen, cyano, alkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylsulphonylamino, alkylsulphonyl, alkylcarbonyl, and alkyl, wherein the alkyl groups have 1-5 carbon atoms, and which intermediate has either the R or the S configuration, by subjecting an optically active cyanohydrin of the general formula to a reduction-transimination-reduction sequence, using R - NH₂ as the primary amine, followed by a cyclization reaction and, finally, by an ozonolysis-reduction sequence.

  本发明涉及一种通式如下的杂环中间体的制备方法 其中 X 是羰基、硫代羰基、(C₁-C₁₀)(ar)亚烷基或二氢羰基硅烷基、 R 是直链或支链(C₁-C₁₀)烷基，可选择被卤素、羟基、(C₁-C₄)烷氧基或受保护羟基取代，或苯基(C₁-C₃)烷基或杂芳基(C₁-C₃)烷基，这些基团可选择被 1-3 个取代基取代、选自由羟基、(C₅-C₁₂)环烷基、氨基、硝基、卤素、氰基、烷氧基、烷基羰氧基、烷基羰基氨基、烷基磺酰基氨基、烷基磺酰基、烷基羰基和烷基组成的组，其中烷基具有 1-5 个碳原子、 将通式如下的具有光学活性的氰醇与具有 R 或 S 构型的中间体反应 以 R - NH₂ 作为伯胺，进行还原-反式-还原反应、 然后进行环化反应，最后进行臭氧分解还原反应。