4-噁唑羧酸,4,5-二氢-2-(4-甲氧苯基)-5-苯基-,甲基酯,反- | 50706-89-3

• 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
• 中文名称: 4-噁唑羧酸,4,5-二氢-2-(4-甲氧苯基)-5-苯基-,甲基酯,反-
• 英文名称: (4S)-2-(4-methoxy-phenyl)-5t-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid methyl ester
• CAS: 50706-89-3；50707-32-9；139334-33-1；139334-34-2
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: DRYCEUITNNQANX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.12
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-噁唑羧酸,4,5-二氢-2-(4-甲氧苯基)-5-苯基-,甲基酯,反- 生成 dl-threo-phenylserine
  参考文献：
  名称：

  Enantioselective synthesis of cis-2-oxazoline-4-car☐ylates by Lewis acid catalyzed formal [3 + 2] cycloadditions of 5-alkoxyoxazoles with aldehydes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10752-3
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 (R)-methylaluminum β-binaphthoxide 、 三乙胺 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 89.0h， 生成 4-噁唑羧酸,4,5-二氢-2-(4-甲氧苯基)-5-苯基-,甲基酯,反-
  参考文献：
  名称：

  Enantioselective synthesis of cis-2-oxazoline-4-car☐ylates by Lewis acid catalyzed formal [3 + 2] cycloadditions of 5-alkoxyoxazoles with aldehydes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10752-3

文献信息

• Cis and Enantioselective Synthesis of 2-Oxazoline-4-carboxylates through Lewis Acid-Catalyzed Formal [3 + 2] Cycloaddition of 5-Alkoxyoxazoles with Aldehydes
  作者：Hiroyuki Suga、Kosei Ikai、Toshikazu Ibata

  DOI：10.1021/jo990525d

  日期：1999.9.1

  In the presence of 2 equiv of (R)-methylaluminum beta-binaphthoxide, which was prepared from (R)-2,2'-dihydroxy-1,1'-binaphthyl and trimethylaluminum, the reaction of 5-methoxy-2-(p-methoxyphenyl)oxazole with benzaldehyde in MeCN gave the corresponding 2-oxazoline-4-carboxylate in high yield (89%) with high stereoselectivity (cis/trans = 92:8) and high enantioselectivity (88% ee (cis)). Under the same conditions, enantioselectivity of the cis products obtained from the reaction with para-substituted benzaldehydes was moderate. On the other hand, formal [3 + 2] cycloaddition of 5-methoxy-2-(o-methoxyphenyl)oxazole with benzaldehyde or para- and meta-substituted benzaldehydes successfully proceeded only in the presence of 30 mol % of (R)-methylaluminum beta-binaphthoxide, which was prepared from (R)-2,2'-dihydroxy-1,1'-binaphthyl and 1.1-1.05 equiv of trimethylaluminum, to give cis-2-oxazoline-4-carboxylates in high enantioselectivity (up to 90% eel.