(S)-5-methyloxazolidin-2-one | 111688-36-9

• 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: (S)-5-methyloxazolidin-2-one
• 英文别名: (5S)-5-methyl-1,3-oxazolidin-2-one
• CAS: 111688-36-9
• 化学式: C₄H₇NO₂
• 分子量: 101.105
• InChiKey: HBRXQSHUXIJOKV-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-methyloxazolidin-2-one 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以27%的产率得到S-1-氨基-2-丙醇
  参考文献：
  名称：

  A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones

  摘要：

  A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from P-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral P-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (similar to 99%) and d.e. (> 99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00364-0
• 作为产物：
  描述：

  (S)-(-)-碳酸丙烯酯 在 cesium fluoride 、 尿素 作用下， 以 二甲基亚砜 为溶剂， 以66.8%的产率得到(S)-5-methyloxazolidin-2-one
  参考文献：
  名称：

  Process for producing oxazolidin-2-one derivative

  摘要：

  一种工业制备氧唑烷-2-酮衍生物的工艺，表示为以下通式（3），其中R1、R2、R3和R4分别为氢原子、直链、支链或环烷基，被烷氧基、取代氨基或烷硫基取代的直链或支链烷基，取代或未取代芳基或取代或未取代芳基，R5为氢原子、直链、支链或环烷基，取代或未取代芳基，或取代或未取代芳环，其特征在于在氟化盐存在下，使1,3-二氧杂环-2-酮衍生物与碳酸酯衍生物或脲衍生物发生反应。

  公开号：

  US06271388B1

文献信息

• Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates
  作者：Haile Qiu、Xiaofeng Chen、Junliang Zhang

  DOI：10.1039/c9sc04073k

  日期：——

  A novel class of bifunctional cyclic phosphine catalysts (Le-Phos) is reported, which showed good performances in enantioselective γ-addition reactions of N-centered nucleophiles and allenoates under mild conditions.

  一种新型的双功能环磷催化剂（Le-Phos）被报道，它在温和条件下对N-中心亲核试剂和烯酸酯的对映选择性γ-加成反应中表现出良好的性能。
• Photochemically induced radical alkynylation of C(sp³)–H bonds
  作者：Tamaki Hoshikawa、Shin Kamijo、Masayuki Inoue

  DOI：10.1039/c2ob26785c

  日期：——

  C(sp3)–H bonds has been developed. After C–H abstraction by the photo-excited benzophenone, a two-carbon unit was efficiently transferred to the generated radical from 1-tosyl-2-(trimethylsilyl)acetylene to afford the alkynylated product. The present reaction enables construction of various tri- and tetra-substituted carbons from heteroatom-substituted methylenes, methines and alkanes in a highly chemoselective

  已经开发出一种用于光化学炔化未反应的C（sp 3）–H键的通用策略。通过光激发的二苯甲酮将C–H抽象化后，一个两碳单元被有效地转移至由1-甲苯磺酰基-2-（三甲基甲硅烷基）乙炔得到炔基化产物。本反应使得能够以高度化学选择性的方式由杂原子取代的亚甲基，次甲基和烷烃构造各种三和四取代的碳，并且将用作快速构建复杂结构的新合成策略。
• OXAZOLIDIN-2-ONE COMPOUNDS AND USES THEREOF
  申请人：Novartis AG

  公开号：US20130225574A1

  公开（公告）日：2013-08-29

  The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

  本发明涉及氧唑烷-2-酮取代嘧啶化合物，其作为PI3K（磷脂酰肌醇-3-激酶）抑制剂，以及其药物组合物、制备方法和用于治疗依赖于PI3K的疾病、病症和疾病的用途。
• Efficient Routes to a Diverse Array of Amino Alcohol-Derived Chiral Fragments
  作者：Sina Haftchenary、Shawn D. Nelson、Laura Furst、Sivaraman Dandapani、Steven J. Ferrara、Žarko V. Bošković、Samuel Figueroa Lazú、Adrian M. Guerrero、Juan C. Serrano、DeMarcus K. Crews、Cristina Brackeen、Jeffrey Mowat、Thomas Brumby、Marcus Bauser、Stuart L. Schreiber、Andrew J. Phillips

  DOI：10.1021/acscombsci.6b00050

  日期：2016.9.12

  Efficient syntheses of chiral fragments derived from chiral amino alcohols are described. Several unique scaffolds were readily accessed in 1–5 synthetic steps leading to 45 chiral fragments, including oxazolidinones, morpholinones, lactams, and sultams. These fragments have molecular weights ranging from 100 to 255 Da and are soluble in water (0.085 to >15 mM).

  描述了衍生自手性氨基醇的手性片段的有效合成。在1-5个合成步骤中，很容易获得几个独特的支架，这些支架导致45个手性片段，包括恶唑烷酮，吗啉酮，内酰胺和sultams。这些片段的分子量为100至255 Da，可溶于水（0.085至> 15 mM）。
• Direct Catalytic Synthesis of Enantiopure 5-Substituted Oxazolidinones from Racemic Terminal Epoxides
  作者：Giuseppe Bartoli、Marcella Bosco、Armando Carlone、Manuela Locatelli、Paolo Melchiorre、Letizia Sambri

  DOI：10.1021/ol050675c

  日期：2005.5.1

  A venerable scaffold for asymmetric synthesis and drug development, chiral 5-substituted oxazolidinones are obtained in almost enantiomerically pure form (up to 99.9% ee) starting from racemic terminal epoxides. The salient features of this process include the very simple and convenient experimental protocol and the employment of a readily accessible catalyst and inexpensive, easily handled starting

  作为用于不对称合成和药物开发的古老支架，从外消旋末端环氧化物开始，以几乎对映体纯的形式（高达99.9％ee）获得手性5取代的恶唑烷酮。该方法的显着特征包括非常简单和方便的实验方案，以及使用易于获得的催化剂和廉价，易于处理的原料。还描述了将外消旋环氧化物完全转化为单一立体异构的恶唑烷酮的对映体收敛方法。