5-(氯甲基)-3-苯基-1,3-恶唑烷-2-酮 | 711-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-(氯甲基)-3-苯基-1,3-恶唑烷-2-酮
• 中文别名: 5-(氯甲基)-3-苯基-1,3-噁唑烷-2-酮
• 英文名称: 5-(chloromethyl)-3-phenyl-1,3-oxazolidin-2-one
• 英文别名: 5-chloromethyl-3-phenyl-1,3-dioxazolidin-2-one；3-phenyl-2-oxo-5-(chloromethyl)oxazolidine；5-(chloromethyl)-3-phenyl-oxazolidin-2-one；5-(chloromethyl)-3-phenyloxazolidin-2-one；3-phenyl-5-chloromethyloxazolidin-2-one；5-chloromethyl-3-phenyloxazolidin-2-one
• CAS: 711-85-3
• 化学式: C₁₀H₁₀ClNO₂
• mdl: MFCD01024968
• 分子量: 211.648
• InChiKey: KARLWXPEKSFFJC-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  315.8±11.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(氯甲基)-3-苯基-1,3-恶唑烷-2-酮 在 chlorosulphuric acid 作用下， 反应 1.0h， 生成 4-(5-Chloromethyl-2-oxo-oxazolidin-3-yl)-benzenesulfonyl chloride
  参考文献：
  名称：

  Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group

  摘要：

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.

  DOI：

  10.1021/jm00128a003
• 作为产物：
  描述：

  phenyl-carbamic acid-(β,β'-dichloro-isopropyl ester) 在 potassium fluoride 、 苄基三乙基氯化铵 作用下， 以 水 、 甲苯 为溶剂， 以83%的产率得到5-(氯甲基)-3-苯基-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  氟-阴离子促进的氨基烯烃官能团在1,2,3-三醇，1,3-二卤代丙烷-2-醇和2,3-二卤代丙醇中的区域特异性引入

  摘要：

  1,2,3-三醇，1,3-二卤代丙烷-2-醇和2,3-二卤代丙醇衍生物的区域特异性转化为氟阴离子促进的恶唑烷-2-酮和/或恶唑-2（3 H）-酮。被描述。

  DOI：

  10.1039/c39870000689

文献信息

• Chemoselective CaO-Mediated Acylation of Alcohols and Amines in 2-Methyltetrahydrofuran
  作者：Vittorio Pace、Pilar Hoyos、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1002/cssc.201200922

  日期：2013.5

  Calcium oxide is proposed as an innocuous acid scavenger for the chemoselective synthesis of amide‐ and ester‐type compounds. Although these molecules have wide spread applications in organic and pharmaceutical chemistry, and a large number of routes have been designed for their synthesis, the development of more efficient and environmentally friendly acylation strategies remains an ongoing challenge

  氧化钙被提议作为酰胺和酯类化合物化学选择性合成的无害酸清除剂。尽管这些分子在有机和药物化学中具有广泛的应用，并且已经设计了许多合成途径，但是开发更有效和对环境友好的酰化策略仍然是一项持续的挑战。CaO的使用允许在酚或叔醇存在下伯醇的化学计量酰化；胺还可以在羟基存在下进行酰化反应。如果起始原料是光学纯的醇或使用手性酰化剂，则通过酰化获得手性。此外，使用更环保的溶剂2-甲基四氢呋喃（2-MeTHF），导致产量最大化。该协议已成功应用于有趣的综合N-芳基恶唑烷-2-酮中间体，用于制备利奈唑胺类化合物。
• Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations
  作者：Yang Zhang、Yan Zhang、Sheng Xie、Mingdi Yan、Olof Ramström

  DOI：10.1016/j.catcom.2016.04.009

  日期：2016.7

  A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stereoselectivity in sequential O- and N-alkoxycarbonylation processes.

  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。
• 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。
• Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols
  作者：Teemu Niemi、Israel Fernández、Bethany Steadman、Jere K. Mannisto、Timo Repo

  DOI：10.1039/c8cc00636a

  日期：——

  for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations

  我们在本文中报道了在外部碱和羟基活化剂存在下由氨基醇和二氧化碳合成环状氨基甲酸酯的简单通用方法。利用对甲苯磺酰氯（TsCl），该反应在温和的条件下进行，该方法完全适用于制备各种高附加值的5-和6-元环以及双环稠合的氨基甲酸酯。DFT计算和实验结果表明具有高区域选择性，化学选择性和立体选择性的S N 2型反应机理。
• Microwave-Assisted Electrostatically Enhanced Phenol-Catalyzed Synthesis of Oxazolidinones
  作者：Ali Rostami、Amirhossein Ebrahimi、Nader Sakhaee、Farhad Golmohammadi、Ahmed Al-Harrasi

  DOI：10.1021/acs.joc.1c01686

  日期：2022.1.7

  one-component organocatalyst for the atom-economic transformation of epoxides to oxazolidinones under microwave irradiation. Integrating a positively charged center into phenols over a modular one-step preparation gives rise to a bifunctional system with improved acidity and activity, competent in rapid assembly of epoxides and isocyanates under microwave irradiation in a short reaction time (20–60 min)

  静电增强的苯酚被用作一种简单、可持续和有效的单组分有机催化剂，用于在微波照射下将环氧化物原子经济地转化为恶唑烷酮。通过模块化的一步制备将带正电荷的中心整合到酚类中，产生了一个双功能体系，具有改善的酸度和活性，能够在微波照射下在短反应时间（20-60 分钟）内快速组装环氧化物和异氰酸酯。仔细评估了各种带正电荷的苯酚和苯胺的功效，并检查了催化剂负载、温度和亲核试剂种类等几个因素对催化反应性的影响。在整洁的条件下，利用这一单组分催化平台，可在数分钟内从各种芳基和烷基取代的环氧化物和异氰酸酯制备 40 多个恶唑烷酮实例，实现了高达 96% 的收率和高选择性。进行了 DFT 计算以实现不同催化途径的反应势垒，以提供机理理解并证实了其中提出的同时环氧化物开环和异氰酸酯掺入的实验结果。