methyl (4R,5S)-4-methyl-2-oxotetrahydopyrrole-5-carboxylate | 120239-79-4

• 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: methyl (4R,5S)-4-methyl-2-oxotetrahydopyrrole-5-carboxylate
• 英文别名: (+)-(2S,3R)-methyl-3-methyl-5-oxopyrrolidine-2-carboxylate；L-Proline, 3-methyl-5-oxo-, methyl ester, cis-；methyl (2S,3R)-3-methyl-5-oxopyrrolidine-2-carboxylate
• CAS: 120239-79-4
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: VUGCWZURFXUZJX-XINAWCOVSA-N

物化性质

• 沸点：
  301.2±35.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3R)-3-methylglutamic acid 以 水 为溶剂， 反应 12.0h， 生成 methyl (4R,5S)-4-methyl-2-oxotetrahydopyrrole-5-carboxylate
  参考文献：
  名称：

  Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid

  摘要：

  Arndt-Eistert homologation of suitably-protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3- Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether. of cyclo-(R-Val-Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid. Both conjugate additions occurred with high diastereoselectivity.

  DOI：

  10.1039/p19940002525

文献信息

• Organocatalytic Asymmetric Conjugate Addition to Allenic Esters and Ketones
  作者：Petteri Elsner、Luca Bernardi、Giorgio Dela Salla、Jacob Overgaard、Karl Anker Jørgensen

  DOI：10.1021/ja710689c

  日期：2008.4.1

  having different ring sizes, ring systems, and substituents in high yields and enantioselectivities. Glycine imine derivatives also undergo the asymmetric conjugate addition to electron-deficient allenes in high yields and with enantioselectivities in the range of 60-88% ee, thus providing a rapid entry to optically active alpha-vinyl-substituted alpha-amino acid derivatives. It is shown that the enantioselectivity

  描述了环状β-酮酯和甘氨酸亚胺衍生物与缺电子丙二烯的有机催化对映选择性共轭加成的第一个例子。我们公开了相应的手性 β，γ-不饱和羰基化合物仅在相转移条件下使用金鸡纳生物碱衍生或联苯基手性季铵盐作为催化剂形成。β-酮酯的反应范围概述了具有酮或酯基序作为吸电子基团的丙二烯以及在 3 位具有不同取代基的丙二烯，从而以高产率和优异的非对映选择性和对映选择性得到旋光产物（ 90-96% ee)。对于许多具有不同环大小、环系统、和高产率和对映选择性的取代基。甘氨酸亚胺衍生物还以高产率与缺电子丙二烯进行不对称共轭加成，对映选择性在 60-88% ee 范围内，从而快速进入光学活性 α-乙烯基取代的 α-氨基酸衍生物。结果表明，对映选择性强烈依赖于亲核试剂的酯部分与所用催化体系的结合。这些新的催化过程产生的手性产物的高合成价值通过两种直接的转化得到证明，一种是光学活性的六氢苯并吡喃酮，另一种是取代的焦谷氨
• 2-Hydroxy-3-pinamone as chiral auxiliary in the asymmetric synthesis of α-amino acids
  作者：Abdelrani El Achqar、Mohamed Boumzebra、Marie-Louise Roumestant、Philippe Viallefont

  DOI：10.1016/s0040-4020(01)86039-7

  日期：1988.1

  The reactivity of lithiated chiral Schiff bases 2 with carbonyl compounds is studied. They do not react with ketones but with aldehydes good chemical yields are obtained in the presence of cosolvents. On the other hand, the reaction with unsaturated carbonyl compounds (ethylenic, acetylenic, allenic) is very rapid and affords a variety of amino esters with good chemical and optical yields. With the

  研究了锂化手性席夫碱2与羰基化合物的反应性。它们不与酮反应，但与醛反应，在助溶剂存在下可获得良好的化学收率。另一方面，与不饱和羰基化合物（烯键，炔键，烯丙基）的反应非常迅速，并提供了具有良好化学和光学收率的多种氨基酯。对于通过将甘氨酸的酯与2-羟基3-吡喃酮环化而制备的内酯7，用卤代烷，醛和环氧化物得到的第一个结果显示出极好的立体选择性和良好的化学收率。
• Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid
  作者：Basil Hartzoulakis、David Gani

  DOI：10.1039/p19940002525

  日期：——

  Arndt-Eistert homologation of suitably-protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3- Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether. of cyclo-(R-Val-Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid. Both conjugate additions occurred with high diastereoselectivity.