trans-4-Methoxycarbonyl-2-(p-methoxyphenyl)-5-(p-nitrophenyl)-2-oxazoline | 139334-35-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-4-Methoxycarbonyl-2-(p-methoxyphenyl)-5-(p-nitrophenyl)-2-oxazoline
• 英文别名: methyl (4S,5R)-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 139334-35-3；139334-36-4
• 化学式: C₁₈H₁₆N₂O₆
• 分子量: 356.335
• InChiKey: QAPDVAAQHJJBDV-JKSUJKDBSA-N

物化性质

• 沸点：
  539.7±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  100.26
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-methoxy-5-(3-methoxyphenyl)-1,3-oxazole 、 对硝基苯甲醛 、 13-Methyl-12,14-dioxa-13-aluminapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 生成 trans-4-Methoxycarbonyl-2-(p-methoxyphenyl)-5-(p-nitrophenyl)-2-oxazoline
  参考文献：
  名称：

  Suga Hiroyuki, Shi Xiaolan, Ibata Toshikazu, J. Org. Chem, 58 (1993) N 26, S 7397-7405

  摘要：

  DOI：

文献信息

• Reactions of 5-alkoxyoxazoles with aldehydes in the presence of Lewis acid: regio- and stereoselective formation of 4-alkoxycarbonyl-2-oxazolines
  作者：Hiroyuki Suga、Xiaolan Shi、Hiroki Fujieda、Toshikazu Ibata

  DOI：10.1016/0040-4039(91)80442-9

  日期：1991.11

  The [3 + 2] cycloaddition of 5-alkoxyoxazoles with aldehydes in the presence of the organoaluminum reagent, which was prepared from (±)-2,2′-dihydroxy-1,1′-dinaphthyl and AlMe3, gave cis-4-alkoxycarbonyl-2-oxazolines in high regio- and stereoselective manner.

  由（±）-2,2'-二羟基-1,1'-二萘基和AlMe 3制备的有机铝试剂在5-烷氧基恶唑与醛的[3 + 2]环加成反应中得到顺式-4 -烷氧基羰基-2-恶唑啉具有高区域和立体选择性。
• Enantioselective synthesis of cis-2-oxazoline-4-car☐ylates by Lewis acid catalyzed formal [3 + 2] cycloadditions of 5-alkoxyoxazoles with aldehydes
  作者：Hiroyuki Suga、Kosei Ikai、Toshikazu Ibata

  DOI：10.1016/s0040-4039(97)10752-3

  日期：1998.2

  Formal [3 + 2] cycloaddition of 2-o-methoxyphenyl-5-methoxyoxazole with benzaldehyde, m- and p-substituted benzaldehydes in the presence of 30 mol% of (R)-methylaluminum beta-binaphthoxide, which was prepared from (R)-2,2'-dihydroxy-1,1'-dinaphthyl and 1.1-1.05 equiv. of trimethylaluminum, gave cis-2-oxazoline-4-carboxylates in high enantoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of 2-oxazoline-4-carboxylates through Lewis acid-catalyzed formal [3+2] cycloadditions of 5-alkoxyoxazoles with aldehydes: catalytic effect of methylaluminum .beta.-binaphthoxide on cis-selectivity
  作者：Hiroyuki Suga、Xiaolan Shi、Toshikazu Ibata

  DOI：10.1021/jo00078a018

  日期：1993.12

  The formal [3 + 2] cycloadditions of 5-methoxy-2-(p-methoxyphenyl)oxazole with benzaldehyde, para- and meta-substituted benzaldehydes, propanal, cinnamaldehyde, and heterocyclic carboxaldehydes in the presence of methylaluminum beta-binaphthoxide gave the corresponding methyl 5-alkyl-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylates with high cis-selectivity (up to 98%). The use of ortho-substituted benzaldehydes resulted in a decrease in the cis-selectivity. The reaction of 5-methoxy-2-(p-methoxyphenyl)oxazole with benzaldehyde in the presence of titanium(IV) chloride or tin(IV) chloride gave the corresponding trans-2-oxazoline-4-carboxylate with 85-86% trans-selectivity. The reaction of ethyl glyoxylate with 5-ethoxy-2-phenyloxazole catalyzed by a 1:1 mixture of titanium(IV) chloride and titanium tetraisopropoxide gave diethyl 2-phenyl-2-oxazoline-4,5-dicarboxylate with a preference for cis-selectivity (cis/trans = 84:6). The cis-selectivity of the reaction in the presence of methylaluminum beta-binaphthoxide can be explained by an antiperiplanar approach of the C4-C5 double bond of the oxazole to the aldehyde coordinated to the catalyst, followed by ring opening of the oxazole through a stepwise pathway involving zwitterionic intermediates.