N-Formyloxazolidinone | 248252-53-1

• 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: N-Formyloxazolidinone
• 英文别名: 2-oxazolidinone；N-formyl-oxazolidinone；2-oxo-1,3-oxazolidine-3-carbaldehyde
• CAS: 248252-53-1
• 化学式: C₄H₅NO₃
• 分子量: 115.089
• InChiKey: JRZSJAZVEWNVFA-UHFFFAOYSA-N

物化性质

• 沸点：
  168.1±23.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Formyloxazolidinone 在 碳酸氢钠 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 以14 mg的产率得到2-唑烷酮
  参考文献：
  名称：

  钌，酰胺，内酰胺，酰亚胺和同类物中烯丙基保护基的实际钌催化裂解。

  摘要：

  开发了一种方便的方法，用于脱保护N-烯丙基酰胺样部分。通过顺序使用Grubbs卡宾（异构化步骤）和RuCl（3）（氧化步骤）获得了第一个实例，说明了钌催化的酰胺，内酰胺，酰亚胺，吡唑烷酮，乙内酰脲和恶唑烷酮的脱羧反应。可以使用多种底物，包括对映纯多功能β-和γ-内酰胺。

  DOI：

  10.1002/chem.200501227
• 作为产物：
  描述：

  Se-phenyl 2-oxo-1,3-oxazolidine-3-carboselenoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以99%的产率得到N-Formyloxazolidinone
  参考文献：
  名称：

  Generation and Reactivity of Oxazolidinone Derived N-Acyl Radicals

  摘要：

  用三光气处理噁唑烷酮的锂盐，然后加入苯硒醇，制备出 N-酰基（苯基硒）噁唑烷酮 5（收率 85%）。用 n-Bu3SnH/AIBN 还原 5 得到 N-甲酰噁唑烷酮 6（99%），与烯丙基三丁基锡烷反应得到 7（89%）。此外，还研究了利用从噁唑烷酮 5 衍生的 N-酰基对各种烯烃进行双分子加成的情况。富电子烯烃（如烯醇醚衍生物）的效果最好。报告中介绍了八种这样的加成反应，产率在 51-90% 之间。在与 5/Bu3SnH 的反应中，两种亲手性底物显示出显著的非对映选择性。

  DOI：

  10.1055/s-1999-2913

文献信息

• Metal‐Ligand Cooperativity in Mn ^I ‐Catalysed N‐Formylation of Secondary Amides and Lactams Using CO ₂ at Room Temperature
  作者：Soumi Chakraborty、Rounak Nath、Anuj Kumar Ray、Ankan Paul、Swadhin K. Mandal

  DOI：10.1002/chem.202202710

  日期：2023.2

  A MnI complex coordinated with a redox non-innocent phenalenyl (PLY) ligand is reported for catalytic N-formylation of secondary amides (including late-stage diversification of pharmaceutics) and lactams with CO2 as C1 source at room temperature for the first time. A combined approach of experimental analysis and DFT calculations sketch the plausible radical-mediated pathway of an unconventional metal-ligand

  据报道， Mn I络合物与氧化还原非无害苯二甲酰 (PLY) 配体配位，首次在室温下以 CO 2作为 C 1源催化仲酰胺（包括后期药物多样化）和内酰胺的 N-甲酰化时间。实验分析和 DFT 计算的组合方法描绘了一种非常规金属-配体合作的可能的自由基介导途径，涉及以配体为中心的自由基。
• Stereocontrol within Confined Spaces:  Enantioselective Photooxidation of Enecarbamates Inside Zeolite Supercages
  作者：J. Sivaguru、Thomas Poon、Roberto Franz、Steffen Jockusch、Waldemar Adam、Nicholas J. Turro

  DOI：10.1021/ja046115a

  日期：2004.9.1

  Dye-exchanged Y zeolite is shown to be an effective medium to control the stereoselectivity in the photooxygenation of chiral oxazolidinone-functionalized Z/E-1 enecarbamates. An enantioselectivity (ee) as high as 80% was observed in the methyldesoxybenzoin (MDB) product, obtained in the methylene-blue-exchanged NaY zeolite at room temperature. The efficacy of the asymmetric induction in the MDB product depends on the Z/E geometry of the alkene, the Z-isomer being more effective than the corresponding E-isomer. The stereoselectivity is rationalized in terms of conformational effects through cationic interactions between the zeolite and the substrate.
• Stereochemical Features of the Physical and Chemical Interactions of Singlet Oxygen with Enecarbamates
  作者：Thomas Poon、Nicholas J. Turro、Jessica Chapman、P. Lakshminarasimhan、Xuegong Lei、Steffen Jockusch、Roberto Franz、Ilyas Washington、Waldemar Adam、Sara G. Bosio

  DOI：10.1021/ol035856y

  日期：2003.12.1

  [GRAPHICS]Oxazolidinone-substituted enecarbamates represent a mechanistically rich system for the study of stereoelectronic, steric, and conformational effects on stereoselectivity and mode selectivity in O-1(2) [2 + 2] and ene reactions. Photooxygenation of these enecarbamates with O-1(2) leads to diastereomerically pure dioxetanes that decompose to yield an oxazolidinone carbaldehyde and one of the two enantiomers of methyldesoxybenzoin in enantiomeric excess. Stereoselectivity originates at the allylic stereocenter, a result supported by quenching studies, computational analysis, and deuterium solvent isotope effects.
• A Practical Ruthenium-Catalyzed Cleavage of the Allyl Protecting Group in Amides, Lactams, Imides, and Congeners
  作者：Benito Alcaide、Pedro Almendros、Jose M. Alonso

  DOI：10.1002/chem.200501227

  日期：2006.3.20

  deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl(3) (oxidation step). A variety of substrates, including enantiopure multifunctional beta- and gamma-lactams, can

  开发了一种方便的方法，用于脱保护N-烯丙基酰胺样部分。通过顺序使用Grubbs卡宾（异构化步骤）和RuCl（3）（氧化步骤）获得了第一个实例，说明了钌催化的酰胺，内酰胺，酰亚胺，吡唑烷酮，乙内酰脲和恶唑烷酮的脱羧反应。可以使用多种底物，包括对映纯多功能β-和γ-内酰胺。
• Generation and Reactivity of Oxazolidinone Derived N-Acyl Radicals
  作者：Gary E. Keck、Mark C. Grier

  DOI：10.1055/s-1999-2913

  日期：——

  The N-acyl(phenylseleno)oxazolidinone 5 was prepared (85% yield) by treatment of the lithium salt of oxazolidinone with triphosgene, followed by addition of benzeneselenol. Reduction of 5 with n-Bu3SnH/AIBN gave the N-formyloxazolidinone 6 (99%) and reaction with allyltri-n-butylstannane gave 7 (89%). Bimolecular additions to various alkenes using the N-acyl radical derived from oxazolidinone 5 were also studied. Best results were obtained with electron rich olefins, such as enol ether derivatives. Eight such additions are reported, with yields ranging from 51-90%. Two prochiral substrates showed significant levels of diastereoselectivity in reactions with 5/Bu3SnH.

  用三光气处理噁唑烷酮的锂盐，然后加入苯硒醇，制备出 N-酰基（苯基硒）噁唑烷酮 5（收率 85%）。用 n-Bu3SnH/AIBN 还原 5 得到 N-甲酰噁唑烷酮 6（99%），与烯丙基三丁基锡烷反应得到 7（89%）。此外，还研究了利用从噁唑烷酮 5 衍生的 N-酰基对各种烯烃进行双分子加成的情况。富电子烯烃（如烯醇醚衍生物）的效果最好。报告中介绍了八种这样的加成反应，产率在 51-90% 之间。在与 5/Bu3SnH 的反应中，两种亲手性底物显示出显著的非对映选择性。