methyl trans-3-methyl-5-oxo-2-pyrrolidinecarboxylate | 76251-46-2

• 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 trans-3-methyl-5-oxo-2-pyrrolidinecarboxylate
• 英文别名: methyl trans-3-methylpyroglutamate；methyl (2S,3S)-3-methyl-5-oxopyrrolidine-2-carboxylate
• CAS: 76251-46-2
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: VUGCWZURFXUZJX-NJGYIYPDSA-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

• 作为反应物：
  描述：

  methyl trans-3-methyl-5-oxo-2-pyrrolidinecarboxylate 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 21.5h， 生成 N-(p-toluenesulfonyl)-trans-3-methylproline
  参考文献：
  名称：

  Diastereoisomers of 3-methylpyroglutamic acid and .beta.-methylglutamic acid

  摘要：

  DOI：

  10.1021/jo00318a042
• 作为产物：
  描述：

  methyl (3S,2'S,5'R)-3-<5'-isopropyl-3',6'-dimethoxy-2',5'-dihydropyrazin-2'-yl>butanoate 在 盐酸 、 D,L-valine 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 methyl trans-3-methyl-5-oxo-2-pyrrolidinecarboxylate
  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
• Synthesis of non-proteinogenic amino acids using Michael addition to unsaturated orthopyroglutamate derivative
  作者：Makoto Oba、Tsuneki Saegusa、Naohiro Nishiyama、Kozaburo Nishiyama

  DOI：10.1016/j.tet.2008.10.092

  日期：2009.1

  Stereoselective synthesis of non-proteinogenic amino acids via Michael addition to 3,4-didehydropyroglutamate derivative in which the carboxyl function is protected as a 2,7,8-trioxabicyclo[3.2.1]octane (ABO ester) group is described. The obtained 3-substituted pyroglutamic ABO ester was directly converted to 3-substituted glutamic acids such as chlorpheg by acidic hydrolysis, whereas 3-substituted

  描述了通过将Michael加成3,4-didehydropyropyglutamate衍生物（其中羧基官能团被保护为2,7,8-三氧双环[3.2.1]辛烷（ABO酯））的立体选择性合成非蛋白质氨基酸的方法。所获得的3-取代的焦谷氨酸ABO酯通过酸性水解直接转化为3-取代的谷氨酸，如绿豆蔻，而内酰胺羰基的化学选择性还原获得了3-取代的脯氨酸衍生物。还描述了巴氯芬（一种γ-氨基丁酸（GABA）类似物）的正式全合成。
• Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides
  作者：Hideo Nagashima、Hidetoshi Wakamatsu、Nobuyasu Ozaki、Tsutomu Ishii、Masakazu Watanabe、Tomonori Tajima、Kenji Itoh

  DOI：10.1021/jo00032a016

  日期：1992.3

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.
• Beani; Bianchi; Baraldi, Arzneimittel-Forschung/Drug Research, 1990, vol. 40, # 11, p. 1187 - 1191
  作者：Beani、Bianchi、Baraldi、Manfredini、Pollini

  DOI：——

  日期：——
• Stereoselective Michael addition of the imines of .alpha.-amino esters in the presence of lithium bromide/1,8-diazabicyclo[5.4.0]undec-7-ene
  作者：Shuji Kanemasa、Osamu Uchida、Eiji Wada

  DOI：10.1021/jo00301a037

  日期：1990.7