(4S,5S)-4-(3,4-difluorophenyl)-5-methyloxazolidin-2-one | 218450-05-6

• 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: (4S,5S)-4-(3,4-difluorophenyl)-5-methyloxazolidin-2-one
• 英文别名: 4(S)-(3,4-difluorophenyl)-5(S)-methyloxazolidin-2-one；(4S,5S)-4-(3,4-difluorophenyl)-5-methyl-1,3-oxazolidin-2-one
• CAS: 218450-05-6
• 化学式: C₁₀H₉F₂NO₂
• 分子量: 213.184
• InChiKey: SIIPMODOOMLRBR-SSDLBLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(3,4-difluorophenyl)-5-methyloxazolidin-2-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 SNAP 7915
  参考文献：
  名称：

  Determination of the relative and absolute stereochemistry of a potent and α1A-selective adrenoceptor antagonist

  摘要：

  The binding affinities and selectivities of antagonists 1-4 for the alpha (1A)-adrenoceptor are dependent on the stereochemical orientation of the groups at the C-4 and C-5 positions of the oxazolidinone ring. The unambiguous assignment of the relative and absolute configurations of the diastereomers of SNAP 7915 (1) is reported. (C) 2000 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0960-894x(00)00524-2
• 作为产物：
  描述：

  (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(3,4-difluorophenyl)-1-propanone oxime 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 生成 (4S,5S)-4-(3,4-difluorophenyl)-5-methyloxazolidin-2-one
  参考文献：
  名称：

  Determination of the relative and absolute stereochemistry of a potent and α1A-selective adrenoceptor antagonist

  摘要：

  The binding affinities and selectivities of antagonists 1-4 for the alpha (1A)-adrenoceptor are dependent on the stereochemical orientation of the groups at the C-4 and C-5 positions of the oxazolidinone ring. The unambiguous assignment of the relative and absolute configurations of the diastereomers of SNAP 7915 (1) is reported. (C) 2000 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0960-894x(00)00524-2

文献信息

• Crystalline pharmaceutically acceptable salts of an oxazolidinone derivative
  申请人：Merck & Co., Inc.

  公开号：US06329393B1

  公开（公告）日：2001-12-11

  A crystalline pharmaceutically acceptable benzenesulfonate salt of Compound A of formula: and solvates thereof are disclosed. Compound A and its benzenesulfonate salts are alpha 1a adrenergic receptor antagonists useful in the treatment of benign prostatic hyperplasia. Pharmaceutical compositions employing the crystalline salts, and processes for making and using the crystalline salts are also disclosed.

  本文披露了化合物A的苯磺酸盐的晶体药用盐及其溶剂化物。化合物A及其苯磺酸盐是α1a肾上腺素能受体拮抗剂，可用于治疗良性前列腺增生症。本文还披露了使用晶体盐的制药组合物以及制备和使用晶体盐的方法。
• Process for preparing &bgr;-hydroxycarbamates and their conversion to oxazolidinones
  申请人：Merck & Co., Inc.

  公开号：US06372911B1

  公开（公告）日：2002-04-16

  A process for preparing a &bgr;-hydroxy carbamate product is disclosed. The process comprises reacting an olefin compound containing at least one carbon-carbon double bond with a carbamate in an aqueous solvent and in the presence of a base, an osmium catalyst, a co-oxidant selected from a halohydantoin, a haloisocyanuric acid, and an alkali metal salt of a haloisocyanuric acid, and optionally an asymmetric ligand, to form a reaction mixture containing the &bgr;-hydroxy carbamate product. The process optionally further comprises treating the &bgr;-hydroxy carbamate product with additional base to form an oxazolidinone. The oxazolidinones are useful as chiral auxiliary agents and as intermediates for the formation of pharmaceutically active substances such as alpha 1 a adrenergic receptor antagonists. A process for preparing nitrogen-functionalized derivatives of the oxazolidinones is also disclosed.

  公开了一种制备&bgr;-羟基氨基甲酸酯产品的方法。该方法包括在水溶剂和碱的存在下，将至少含有一个碳-碳双键的烯烃化合物与氨基甲酸酯反应，并与一种卤代烷二酮、一种卤代异氰尿酸或一种卤代异氰尿酸的碱金属盐等共氧化剂以及可选的不对称配体反应，形成含有&bgr;-羟基氨基甲酸酯产品的反应混合物。该方法还可选地包括使用额外的碱处理&bgr;-羟基氨基甲酸酯产品，以形成噁唑烷酮。噁唑烷酮可用作手性辅助剂和制药活性物质的中间体，例如α1a肾上腺素受体拮抗剂。公开了一种制备噁唑烷酮的氮功能化衍生物的方法。
• Practical Modifications and Applications of the Sharpless Asymmetric Aminohydroxylation in the One-Pot Preparation of Chiral Oxazolidin-2-ones
  作者：Nancy S. Barta、Daniel R. Sidler、Kara B. Somerville、Steven A. Weissman、Robert D. Larsen、Paul J. Reider

  DOI：10.1021/ol006255z

  日期：2000.9.1

  This communication focuses on a convenient, practical one-pot preparation of chiral 4,5-disubstituted oxazolidan-2-ones in good yield with high enantioselectivities, using a modified Sharpless asymmetric aminohydroxylation of beta-substituted styrene derivatives followed by base-mediated ring closure. This procedure has been demonstrated on both small and large scale, utilizing 1, 3-dichloro-5,5-dimethyl

  [反应：见正文]手性恶唑烷-2-酮在手性助剂方面具有合成价值，并且许多具有药学上令人关注的生物学活性。该交流侧重于方便，实用的一锅法制备高收率，高对映选择性的手性4,5-二取代的oxazolidan-2-ones，方法是使用改良的Sharpless不对称氨基羟基化β-取代的苯乙烯衍生物，然后进行碱介导的闭环。已经使用1，3-二氯-5，5-二甲基乙内酰脲作为次氯酸叔丁酯的易于处理的市售替代品在小规模和大规模上证明了该方法。
• De Novo Design of a Novel Oxazolidinone Analogue as a Potent and Selective α_1A Adrenergic Receptor Antagonist with High Oral Bioavailability
  作者：Bharat Lagu、Dake Tian、Yoon Jeon、Chao Li、John M. Wetzel、Dhanapalan Nagarathnam、Quanrong Shen、Carlos Forray、Raymond S. L. Chang、Theodore P. Broten、Richard W. Ransom、Tsing-Bao Chan、Stacey S. O'Malley、Terry W. Schorn、A. David Rodrigues、Kelem Kassahun、Douglas J. Pettibone、Roger Freidinger、Charles Gluchowski

  DOI：10.1021/jm000085e

  日期：2000.7.1
• US6329393B1
  申请人：——

  公开号：US6329393B1

  公开（公告）日：2001-12-11