(R)-α-allyl-norleucine methyl ester | 501380-81-0

• 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: (R)-α-allyl-norleucine methyl ester
• 英文别名: methyl (2R)-2-amino-2-prop-2-enylhexanoate
• CAS: 501380-81-0
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: HMHFTFMYBSSCNL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-α-allyl-norleucine methyl ester 在 甲醇 、 sodium acetate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 methyl 3(R)-[N-(tert-butoxycarbonyl)amino]-3-butyl-2-oxo-1-pyrrolidineacetate
  参考文献：
  名称：

  Synthesis and Dopamine Receptor Modulating Activity of 3-Substituted γ-Lactam Peptidomimetics of l-Prolyl-l-leucyl-glycinamide

  摘要：

  gamma-Lactam. peptidomimetic 2 of Pro-Leu-Gly-NH2 (PLG) was substituted at the 3-position with isobutyl, butyl, and benzyl moieties to give the PLG peptidomimetics 3-5, respectively. These compounds were synthesized to test the hypothesis that attaching a hydrophobic moiety to the lactam ring to mimic the isobutyl side chain of the leucyl residue of PLG would increase the dopamine receptor modulating activity of such peptidomimetics. These peptidomimetics were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to dopamine receptors isolated from bovine striatal membranes. The rank order of effectiveness of the 3-substituent was benzyl > n-butyl > isobutyl > H.

  DOI：

  10.1021/jm020441o
• 作为产物：
  描述：

  (2S,4R)-2-tert-butyl-3-(allyloxycarbonyl)-4-butyl-4-allyloxazolidinone 在 sodium hydroxide 、 四(三苯基膦)钯 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-α-allyl-norleucine methyl ester
  参考文献：
  名称：

  Synthesis and Dopamine Receptor Modulating Activity of 3-Substituted γ-Lactam Peptidomimetics of l-Prolyl-l-leucyl-glycinamide

  摘要：

  gamma-Lactam. peptidomimetic 2 of Pro-Leu-Gly-NH2 (PLG) was substituted at the 3-position with isobutyl, butyl, and benzyl moieties to give the PLG peptidomimetics 3-5, respectively. These compounds were synthesized to test the hypothesis that attaching a hydrophobic moiety to the lactam ring to mimic the isobutyl side chain of the leucyl residue of PLG would increase the dopamine receptor modulating activity of such peptidomimetics. These peptidomimetics were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to dopamine receptors isolated from bovine striatal membranes. The rank order of effectiveness of the 3-substituent was benzyl > n-butyl > isobutyl > H.

  DOI：

  10.1021/jm020441o

文献信息

• Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to α,α-Disubstituted α-Amino Acids
  作者：Liang Wei、Shi-Ming Xu、Qiao Zhu、Chao Che、Chun-Jiang Wang

  DOI：10.1002/anie.201707019

  日期：2017.9.25

  Double duty: An enantioselective allylic alkylation of aldimine esters has been developed by using a synergistic Cu/Pd catalyst system. This strategy provides access to nonproteinogenic α,α-disubstituted α-amino acids in high yield with excellent enantioselectivity. The more challenging double allylic alkylation of glycinate-derived imine esters was also be realized. LG=leaving group.

  双重职责：通过使用协同的Cu / Pd催化剂体系，开发了醛亚胺酯的对映选择性烯丙基烷基化反应。该策略提供了以优异的对映选择性高产率获得非蛋白原性的α，α-二取代的α-氨基酸的途径。还实现了更具挑战性的甘氨酸衍生的亚胺酯的双烯丙基烷基化。LG =离开小组。
• Synthesis and Dopamine Receptor Modulating Activity of 3-Substituted γ-Lactam Peptidomimetics of <scp>l</scp>-Prolyl-<scp>l</scp>-leucyl-glycinamide
  作者：Kristine Dolbeare、Giuseppe F. Pontoriero、Suresh K. Gupta、Ram K. Mishra、Rodney L. Johnson

  DOI：10.1021/jm020441o

  日期：2003.2.1

  gamma-Lactam. peptidomimetic 2 of Pro-Leu-Gly-NH2 (PLG) was substituted at the 3-position with isobutyl, butyl, and benzyl moieties to give the PLG peptidomimetics 3-5, respectively. These compounds were synthesized to test the hypothesis that attaching a hydrophobic moiety to the lactam ring to mimic the isobutyl side chain of the leucyl residue of PLG would increase the dopamine receptor modulating activity of such peptidomimetics. These peptidomimetics were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to dopamine receptors isolated from bovine striatal membranes. The rank order of effectiveness of the 3-substituent was benzyl > n-butyl > isobutyl > H.