(4S,5S)-4-ethyl-5-methyloxazolidin-2-one

• 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: (4S,5S)-4-ethyl-5-methyloxazolidin-2-one
• 英文别名: (4S,5S)-4-ethyl-5-methyl-1,3-oxazolidin-2-one
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: YBSOFYRXTUQFMN-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S_S,2S)-2-methyl-propane-2-sulfinic acid [2-(tert-butyl-dimethyl-silanyloxy)-1-ethyl-propyl]-amide 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4S,5S)-4-ethyl-5-methyloxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines

  摘要：

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.

  DOI：

  10.1021/jo035224p

文献信息

• Copper-Catalyzed Intramolecular C-H Amination
  作者：Dipti N. Barman、Kenneth M. Nicholas

  DOI：10.1002/ejoc.201001160

  日期：2011.2

  The amino-functionalization of tertiary, secondary and benzylic C–H bonds of tethered carbamates and sulfamates by iodosobenzene is catalyzed by CuI-diimine complexes in moderate to good yield. Employing homochiral imine-Cucatalysts affords oxazolidinones and oxathiazinanes with modest enantioselectivity.

  碘代苯对束缚氨基甲酸酯和氨基磺酸酯的叔、仲和苄基 C-H 键的氨基官能化由 CuI-二亚胺配合物催化，产率中等至良好。采用同手性亚胺-Cu 催化剂提供具有适度对映选择性的恶唑烷酮和氧噻嗪烷。
• PYRAZOLYL DERIVATIVES AS SYK INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150191461A1

  公开（公告）日：2015-07-09

  The present invention provides novel pyrazole derivatives of formula I which are potent inhibitors of spleen tyrosine kinase, and are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.

  本发明提供了公式I的新型吡唑衍生物，它们是脾酪氨酸激酶的有效抑制剂，并可用于治疗和预防由该酶介导的疾病，如哮喘、慢性阻塞性肺疾病、类风湿性关节炎和癌症。
• Efficient synthesis of syn-aziridino alcohols by chelation-controlled addition of dialkylzincs and Grignard reagents to N-benzylaziridino aldehydes
  作者：JoséM. Andrés、Noemí de Elena、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4020(99)00879-0

  日期：1999.12

  N-Benzyl aziridino aldehydes, derived from (L)-serine and (L)-threonine react with dialkylzinc and alkylmagnesium halides leading to syn-aziridino alcohols as single or major stereoisomers. The diastereoselec tivity is affected by the nature of the organometallic and the solvent system.

  衍生自（L）-丝氨酸和（L）-苏氨酸的N-苄基叠氮基醛与二烷基锌和卤化烷基镁反应，生成单一或主要的立体异构体的合成叠氮基醇。非对映选择性受有机金属和溶剂体系性质的影响。
• US9242984B2
  申请人：——

  公开号：US9242984B2

  公开（公告）日：2016-01-26
• Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to <i>N</i>-<i>tert</i>-Butanesulfinyl α-Alkoxyaldimines
  作者：Jared W. Evans、Jonathan A. Ellman

  DOI：10.1021/jo035224p

  日期：2003.12.1

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.

表征谱图