(4R,5S)-3,4-dimethyl-5-phenyloxazolidin-2-one | 91049-48-8

• 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: (4R,5S)-3,4-dimethyl-5-phenyloxazolidin-2-one
• 英文别名: 3,4-dimethyl-5-phenyl-oxazolidin-2-one；(4R)-3,4r-dimethyl-5c-phenyl-oxazolidin-2-one；(4R)-3,4r-Dimethyl-5c-phenyl-oxazolidin-2-on；(4R,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 91049-48-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: MNYARIILPGRTQL-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3,4-dimethyl-5-phenyloxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到(1S,2R)-(+)-N-methylephedrine
  参考文献：
  名称：

  Photocycloaddition of N-Acyl Enamines to Aldehydes and Its Application to the Synthesis of Diastereomerically Pure 1,2-Amino Alcohols

  摘要：

  The regio- and stereoselective synthesis of the protected cis-3-aminooxetanes cis-5 and cis-7 is reported. The oxetanes were obtained by the photocycloaddition of aliphatic (6c-e) and aromatic (4, 6a) aldehydes to the corresponding enamides (1a-d,h) or enecarbamates (le-g). The enamine derivatives used in the Paterno-Buchi reaction were either commercially available or prepared from the corresponding acetaldehyde imines 2 by acylation. The oxetane formation proceeded with good-to-excellent simple diastereoselectivity for aromatic aldehydes (56-82% yield) and moderate selectivity for aliphatic aldehydes (46-55% yield). The cis-3-aminooxetanes are precursors for syn- and anti-1,2-amino alcohols. The relative configuration established in the photochemical step was retained upon nucleophilic ring opening between the oxygen atom and carbon atom C-4. By this means, syn-1,2-amino alcohols such as 8 and 10 were available in good yields. In contrast, the N-Boc-protected cis-3-aminooxetanes cis-5e and cis-5f were transformed into anti-1,2-amino alcohols. Upon treatment with trifluoroacetic acid, they underwent an intramolecular nucleophilic substitution at the carbon atom C-2 of the oxetane and the oxazolidinones II and 12 were formed. Because the substitution occurs with inversion of configuration, anti-1,2-amino alcohols, e.g., ephedrine (15), are accessible.

  DOI：

  10.1021/jo9819988
• 作为产物：
  描述：

  在 (rac)-sodium 1-phenylethanolate 作用下， 生成 (4R,5S)-3,4-dimethyl-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  Kinetic resolution of secondary alcohols using proline-derived bicyclic iminium salts

  摘要：

  DOI：

  10.1016/s0040-4039(97)00815-0

文献信息

• Experimental and DFT study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism
  作者：Abdelkarim El Moncef、El Mestafa El Hadrami、Miguel A. González、Elena Zaballos、Ramón J. Zaragozá

  DOI：10.1016/j.tet.2010.04.097

  日期：2010.7

  Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and/or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated

  磺化1,2-氨基醇的N -Boc衍生物，如麻黄碱，伪麻黄碱，去甲麻黄碱，去甲伪麻黄碱，硫代米胺和氯霉素，可得到相应的恶唑烷酮的混合物，具有倒置（赤型衍生物）和/或保留构型（苏式衍生物） ）在C5。我们建议两种机制之间的竞争：通过Boc基团的羰基氧攻击苄基碳引发的分子内S N 2过程，以及通过双重S N 2过程进行的另一种分子内S N 2过程。在赤型衍生物中，第一个机理是主要的，而在苏氨酸中，第一个机理是主要的。两种机制的导数具有相似的能量。这一假设得到理论计算和其他实验分析的支持。
• Ramoplanin derivatives possessing antibacterial activity
  申请人：Raju G. Bore

  公开号：US20060211603A1

  公开（公告）日：2006-09-21

  Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

  新型拉莫普兰衍生物已被披露。这些拉莫普兰衍生物表现出抗菌活性。由于本发明的化合物对革兰氏阳性细菌表现出强效活性，它们是有用的抗微生物药剂。该化合物的合成方法和使用方法也已被披露。
• Carbon Dioxide as a Carbonylating Agent in the Synthesis of 2-Oxazolidinones, 2-Oxazinones, and Cyclic Ureas: Scope and Limitations
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/jo100268n

  日期：2010.5.7

  Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such

  在2-恶唑烷酮，2-恶嗪酮和环状脲的合成中，二氧化碳可用作方便的羰基化剂。通过在碱性介质中处理伯胺或仲胺基团而生成的瞬态氨基甲酸酯阴离子可以用磷酸化剂（如二苯基磷酰叠氮化物（DPPA）和二苯基氯代磷酸酯（DPPC1））活化，也可以用其他类型的亲电试剂（如SOCl 2，TsCl或氯化铝。羟基将活化的氨基甲酸酯分子内捕获导致形成2-恶唑烷酮或2-恶嗪酮，产率高至优异。该方法已成功地用于从相应的二胺合成高达7元环的环状脲。
• [EN] PROCESS FOR PREPARATION OF ERIBULIN AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ÉRIBULINE ET DE SES INTERMÉDIAIRES
  申请人：DR REDDY'S LABORATORIES LTD

  公开号：WO2017203459A1

  公开（公告）日：2017-11-30

  The present application relate to a process for preparation of 4-Methylene tetrahydrofuran compound of formula II, which is useful as an intermediate for the preparation of halichondrin B analogues such as Eribulin.

  本申请涉及一种用于制备4-亚甲基四氢呋喃化合物（化学式II）的过程，该化合物可用作制备卤呋喃B类似物（如厄立布林）的中间体。
• [EN] FLUORINATED ARYL AMIDE COMPOUNDS<br/>[FR] COMPOSÉS FLUORÉS D'ARYLE ET D'AMIDE
  申请人：CASCADE THERAPEUTICS INC

  公开号：WO2009079763A1

  公开（公告）日：2009-07-02

  A compound of Formula I : The compound can be used in the treatment of epilepsy, neuropathic pain, acute and chronic inflammatory pain, migraine, tardive dyskinesia and other related CNS disorders.

  化合物I的公式为：该化合物可用于治疗癫痫、神经病性疼痛、急性和慢性炎症性疼痛、偏头痛、迟发性运动障碍和其他相关的中枢神经系统疾病。