5-benzyl-4-ethoxycarbonyl-4-oxazolin-2-one | 204376-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzyl-4-ethoxycarbonyl-4-oxazolin-2-one
• 英文别名: ethyl 5-benzyl-2-oxo-2,3-dihydrooxazole-4-carboxylate；ethyl 5-benzyl-2-oxo-3H-1,3-oxazole-4-carboxylate
• CAS: 204376-35-2
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: XLBIOWGNSHAAPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzyl-4-ethoxycarbonyl-4-oxazolin-2-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以98%的产率得到5-benzyl-4-hydroxymethyl-4-oxazolin-2-one
  参考文献：
  名称：

  Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters

  摘要：

  New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of alpha-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTf under similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.

  DOI：

  10.1021/jo010630z
• 作为产物：
  描述：

  氨基甲酸苄酯 、 ethyl 3-[(p-nitrobenzenesulfonyl)oxy]-2-oxo-4-phenylbutanoate 在 TSA 作用下， 以 甲苯 为溶剂， 以60%的产率得到5-benzyl-4-ethoxycarbonyl-4-oxazolin-2-one
  参考文献：
  名称：

  Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters

  摘要：

  3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10854-1

文献信息

• Convergent Synthesis of 2-Oxazolone-4-carboxylates Esters by Reaction of Aldehydes with Ambivalent <i>N</i>-Cbz-α-Tosylglycinate Ester
  作者：Masahiro Abe、Baptiste Picard、Michaël De Paolis

  DOI：10.1021/acs.orglett.0c01703

  日期：2020.6.19

  N-Cbz-α-tosylglycinate ester was combined with aldehydes in a redox-neutral sequence leading to 2-oxazolone-4-carboxylates with high functional group tolerance. While the scope of the method was delineated to primary and secondary aliphatic aldehydes as well as aromatics, no racemization occurred with chiral aldehydes such as Garner’s. Hitherto unknown, this process relies on the ambivalent role of

  N -Cbz-α-甲苯磺酰基甘氨酸酯与醛以氧化还原中性顺序结合，产生具有高官能团耐受性的2-恶唑酮-4-羧酸酯。尽管该方法的范围被限定为伯和仲脂族醛以及芳族化合物，但手性醛（如Garner's）未发生外消旋作用。迄今为止未知，该过程依赖于N -Cbz-α-甲苯磺酰基甘氨酸酯作为亲核试剂的矛盾作用。