(5R)-5-chloromethyl-3-phenyl-oxazolidin-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: (5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one
• 英文别名: (R)-5-(chloromethyl)-3-phenyloxazolidin-2-one；5-(chloromethyl)-3-phenyloxazolidin-2-one；5-chloromethyl-3-phenyloxazolidin-2-one；(R,S)-5-Chloromethyl-3-phenyl-oxazolidin-2-one；(5R)-5-(chloromethyl)-3-phenyl-1,3-oxazolidin-2-one
• 化学式: C₁₀H₁₀ClNO₂
• 分子量: 211.648
• InChiKey: KARLWXPEKSFFJC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯胺 在 lithium bromide 、 lipase B from Candida antarctica 作用下， 以 甲苯 为溶剂， 反应 124.0h， 生成 (5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one 、 (R)-1-chloro-3-(phenylamino)propan-2-ol
  参考文献：
  名称：

  脂肪酶催化的3-苯基恶唑烷-2-酮衍生物的动力学拆分：级联O-和N-烷氧羰基化

  摘要：

  已经建立了一种脂肪酶催化的级联动力学拆分方案，用于合成具有优异对映选择性（95％ee）的3-苯基恶唑烷丁-2-酮衍生物。南极假丝酵母脂肪酶B在顺序的O-和N-烷氧羰基化过程中显示出高催化活性和立体选择性。

  DOI：

  10.1016/j.catcom.2016.04.009

文献信息

• A Facile Solvent-Free Synthesis of Chiral Oxazolidinone Derivatives Catalyzed by MgI₂Etherate: An Approach to Enantiopure Synthesis of Linezolid
  作者：Xingxian Zhang、Chengfeng Zhao、Yue Gu

  DOI：10.1002/jhet.970

  日期：2012.9

  cycloaddition of aryl isocyanates with chiral oxiranes catalyzed by MgI2 etherate under solvent‐free conditions was developed to prepare the chiral oxazolidinone derivatives. This methodology has been applied into the practical synthesis of antibacterial drug linezolid.

  开发了在无溶剂条件下由MgI 2醚化物催化的高效手性异氰酸芳基酯与手性环氧乙烷的立体选择环加成反应，以制备手性恶唑烷酮衍生物的方法。该方法已应用于抗菌药物利奈唑胺的实际合成中。
• Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones
  作者：Yang Zhang、Sheng Xie、Mingdi Yan、Olof Ramström

  DOI：10.1016/j.mcat.2019.03.020

  日期：2019.6

  Asymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of β-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbonylations operating in cascade. Various N-aryloxazolidinone derivatives were obtained in high yields and good enantiopurities.

  开发了通过动态动力学拆分法不对称合成N-芳基恶唑烷酮的方法。β-苯胺醇的外消旋反应中使用了钌基催化剂，南极假丝酵母脂肪酶B（CAL-B）被应用在两个选择性的烷氧基羰基化反应中。以高收率和良好的对映体纯度获得了各种N-芳基恶唑烷酮衍生物。
• Surface and Adsorption Properties of Activated Carbon Fabric Prepared from Cellulosic Polymer: Mixed Activation Method
  作者：Surendra Bhati、J.S. Mahur、Savita Dixit、O.N. Choubey

  DOI：10.5012/bkcs.2013.34.2.569

  日期：2013.2.20

  In this study, activated carbon fabric was prepared from a cellulose-based polymer (viscose rayon) via a combination of physical and chemical activation (mixed activation) processes by means of $CO_2$ as a gasifying agent and surface and adsorption properties were evaluated. Experiments were performed to investigate the consequence of activation temperature (750, 800, 850 and $925^\circ}C$), activation time (15, 30, 45 and 60 minutes) and $CO_2$ flow rate (100, 200, 300 and 400 mL/min) on the surface and adsorption properties of ACF. The nitrogen adsorption isotherm at 77 K was measured and used for the determination of surface area, total pore volume, micropore volume, mesopore volume and pore size distribution using BET, t-plot, DR, BJH and DFT methods, respectively. It was observed that BET surface area and TPV increase with rising activation temperature and time due to the formation of new pores and the alteration of micropores into mesopores. It was also found that activation temperature dominantly affects the surface properties of ACF. The adsorption of iodine and $CCl_4$ onto ACF was investigated and both were found to correlate with surface area.

  在这项研究中，通过$CO_2$作为气化剂，采用物理和化学活化（混合活化）工艺，以纤维素聚合物（粘胶人造丝）为原料制备了活性炭织物，并评估了其表面和吸附性能。实验研究了活化温度（750、800、850和$925^\circ}C$）、活化时间（15、30、45和60分钟）和$CO_2$流速（100、200、300和400 mL/min）对活性炭织物表面和吸附性能的影响。测量了77 K下的氮气吸附等温线，并分别采用BET、t-plot、DR、BJH和DFT方法测定表面积、总孔体积、微孔体积、中孔体积和孔径分布。结果表明，由于新孔的形成和微孔向中孔的转变，BET表面积和TPV随着活化温度和时间的升高而增加。还发现活化温度主要影响活性炭织物的表面性质。研究了碘和$CCl_4$在活性炭织物上的吸附情况，发现两者都与表面积有关。
• Polymer-Aided Stereodivergent Synthesis (PASS):  A New Concept for the Discrete Preparation of Optical Antipodes
  作者：Peter ten Holte、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1021/ol015723h

  日期：2001.4.1

  [GRAPHICS]A new concept for the discrete preparation of optical antipodes is reported. The approach makes use of a cyclization/cleavage procedure that has been applied to polymer-supported quasi-meso compound 1, containing a polymeric leaving group and a regular leaving group. Two-directional cyclization leads to the formation and separation of quasi-enantiomers 2 and 3 simultaneously, with one being immobilized and one free in solution. Treatment of 2 and 3 with appropriate nucleophiles gives discrete enantiomers 4 and 5.
• Xie, Yuanyuan; Chen, Xiaodong; Su, Weike, Journal of Chemical Research, 2009, # 2, p. 129 - 132
  作者：Xie, Yuanyuan、Chen, Xiaodong、Su, Weike

  DOI：——

  日期：——