3-(2-phenoxyacetyl)oxazolidin-2-one | 22445-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-phenoxyacetyl)oxazolidin-2-one
• 英文别名: 3-phenoxyacetyl-oxazolidin-2-one；3-(2-Phenoxyacetyl)-1,3-oxazolidin-2-one
• CAS: 22445-79-0
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: RUKXDWSRBCVQSN-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  418.4±28.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-phenoxyacetyl)oxazolidin-2-one 、 N-thiocyanatosuccinimide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以54%的产率得到3-(2-phenoxy-2-thiocyanatoacetyl)oxazolidin-2-one
  参考文献：
  名称：

  Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

  摘要：

  Electrophilic alpha-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. alpha-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.034
• 作为产物：
  描述：

  苯氧乙酰氯 在 氧气 、 高氯酸四乙基铵 作用下， 生成 3-(2-phenoxyacetyl)oxazolidin-2-one
  参考文献：
  名称：

  Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

  摘要：

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.

  DOI：

  10.1021/jo970308h

文献信息

• Formation of<i>N</i>-Tributylstannyl Heterocycle from Bis(tributyltin) Oxide and ω-Haloalkyl Isocyanate. One-Pot Convenient Synthesis of 2-Oxazolidinones and Tetrahydro-2<i>H</i>-1,3-oxazin-2-one
  作者：Ikuya Shibata、Kenji Nakamura、Akio Baba、Haruo Matsuda

  DOI：10.1246/bcsj.62.853

  日期：1989.3

  Novel types of compounds, N-tributylstannyl-2-oxazolidinone (4a) and tetrahydro-2H-1,3-oxazin-2-one (4b), are formed from the adduct of (n-Bu3Sn)2O (1) with ω-haloalkyl isocyanate (2), and the subsequent coupling reaction with alkyl halides gives a variety of N-substituted 2-oxazolidinones and tetrahydro-2-oxazinones in a one-pot procedure. Both the cyclization and the coupling reaction proceed quantitatively in the presence of HMPA which enhances the reactivity of the Sn–heteroatom bond by coordination.

  新型化合物N-三正丁基锡-2-噁唑烷酮 (4a) 和四氢-2H-1,3-噁唑啉-2-酮 (4b) 是由(n-Bu3Sn)2O (1) 与ω-卤烷基异氰酸酯 (2)的加合物形成的。随后与烷基卤化物的偶联反应在一锅中生成多种N-取代的2-噁唑烷酮和四氢-2-噁唑啉酮。在HMPA的存在下，环化和偶联反应都以定量方式进行，HMPA通过配位增强了Sn–杂原子键的反应性。
• Formation of N-tributylstannyl-2-oxazolidone from (Bu3Sn)2O and 2-chloroethyl isocyanate
  作者：Ikuya Shibata、Akio Baba、Haruo Matsuda

  DOI：10.1039/c39860001703

  日期：——

  N-Tributylstannyl-2-oxazolidone is formed from the reaction of (Bu3Sn)2O and 2-chloroethyl isocyanate in the presence of hexamethylphosphoric triamide, and reacts with electrophiles to give N-substituted 2-oxazolidones in good yields.

  N-三丁基锡烷基-2-恶唑烷酮由（Bu 3 Sn）2 O和2-氯乙基异氰酸酯在六甲基磷酸三酰胺的存在下反应形成，并与亲电试剂反应以高收率得到N-取代的2-恶唑烷酮。
• SHIBATA, IKUYA;NAKAMURA, KENJI;BABA, AKIO;MATSUDA, HARUO, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 853-859
  作者：SHIBATA, IKUYA、NAKAMURA, KENJI、BABA, AKIO、MATSUDA, HARUO

  DOI：——

  日期：——
• SHIBATA IKUYA; BABA AKIO; MATSUDA HARUO, J. CHEM. SOC. CHEM. COMMUN.,(1986) N 23, 1703-1704
  作者：SHIBATA IKUYA、 BABA AKIO、 MATSUDA HARUO

  DOI：——

  日期：——
• Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates
  作者：Maria Antonietta Casadei、Franco Micheletti Moracci、Giovanni Zappia、Achille Inesi、Leucio Rossi

  DOI：10.1021/jo970308h

  日期：1997.10.1

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.