Ethyl trans-3-isopropyloxirane-2-carboxylate | 52945-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Ethyl trans-3-isopropyloxirane-2-carboxylate
• 英文别名: ethyl 3-isopropyloxiranecarboxylate；Ethyl (2R,3S)-3-propan-2-yloxirane-2-carboxylate
• CAS: 52945-83-2；52945-84-3；82235-00-5；136889-94-6；136889-95-7；145631-84-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: HPSAABPQZURAKQ-NKWVEPMBSA-N

物化性质

• 沸点：
  177.8±15.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl trans-3-isopropyloxirane-2-carboxylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,3R)-1-(3,5-Dinitro-benzoyl)-3-isopropyl-aziridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  氮丙啶-2-羧酸酯的便捷合成

  摘要：

  用叠氮化钠处理由使用Sharpless环氧化的烯丙基醇制备的旋光环氧乙烷-2-羧酸酯。随后通过与三苯基膦反应以高收率和高光学纯度将获得的叠氮基醇转化为氮丙啶-2-羧酸酯。使各种外消旋环氧乙烷-2-羧酸酯进行相同的反应顺序。

  DOI：

  10.1002/recl.19921110101
• 作为产物：
  描述：

  4-methyl-1,3-bis<(trimethylsilyl)oxy>-1-ethoxy-1-pentene 在 sodium methylate 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 3.0h， 生成 Ethyl trans-3-isopropyloxirane-2-carboxylate
  参考文献：
  名称：

  Synthesis and reactions of 3-hydroxy-2-nosyloxy esters produced by the stereoselective reduction of 2-nosyloxy-3-keto esters

  摘要：

  The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters. The reduction is stereoselective for the syn isomer. The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters. The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters. As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.

  DOI：

  10.1021/jo00024a013

文献信息

• Synthesis of β-amino α-hydroxy carboxylic esters from oxiranecarboxylic esters
  作者：Johan Legters、Erik van Dienst、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/recl.19921110202

  日期：——

  prepared from the corresponding 3-aryl-oxirane-2-carboxylic esters by ring opening with sodium azide, were reduced with tin(II) chloride dihydrate in methanol to give 3-amino-3-aryl-2-hydroxypropanoic esters in good yields. Under these conditions, halogen substituents in the aromatic rings were not affected. The nitro group, however, was partially reduced to the amino group. Treatment of aliphatic oxirane-2-carboxylic

  由相应的3-芳基-环氧乙烷-2-羧酸酯与叠氮化钠开环制备的3-芳基-3-叠氮基-2-羟基丙酸酯，在甲醇中用氯化锡（II）二水合物还原，得到3-氨基-3-芳基-2-羟基丙酸酯产率高。在这些条件下，芳环中的卤素取代基不受影响。然而，硝基部分还原为氨基。在三氟化硼醚化物的存在下用乙腈处理脂肪族环氧乙烷-2-羧酸酯会导致区域特异性形成2，4-二烷基-2-恶唑啉-5-羧酸酯，这是由于腈在C3处的反应所致。这些恶唑啉-5-羧酸酯的酸性水解得到相应的3-（酰基氨基）-2-羟基羧酸酯。通过这两种互补的方法，
• Synthetic transformations using arenesulfonyloxy groups, first as electrophiles, then as leaving groups
  作者：Robert V. Hoffman

  DOI：10.1016/s0040-4020(01)86369-9

  日期：1991.1
• Pergola, R. Della; Battista, P. Di, Synthetic Communications, 1984, vol. 14, # 2, p. 121 - 126
  作者：Pergola, R. Della、Battista, P. Di

  DOI：——

  日期：——
• A convenient synthesis of aziridine-2-carboxylic esters
  作者：Johan Legters、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/recl.19921110101

  日期：——

  Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide. The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity. Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of

  用叠氮化钠处理由使用Sharpless环氧化的烯丙基醇制备的旋光环氧乙烷-2-羧酸酯。随后通过与三苯基膦反应以高收率和高光学纯度将获得的叠氮基醇转化为氮丙啶-2-羧酸酯。使各种外消旋环氧乙烷-2-羧酸酯进行相同的反应顺序。
• Synthesis and reactions of 3-hydroxy-2-nosyloxy esters produced by the stereoselective reduction of 2-nosyloxy-3-keto esters
  作者：Robert V. Hoffman、Hwa Ok Kim

  DOI：10.1021/jo00024a013

  日期：1991.11

  The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters. The reduction is stereoselective for the syn isomer. The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters. The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters. As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.