(S)-N-allyloxycarbonyl-α-allyl-phenylalanine methyl ester | 501380-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-allyloxycarbonyl-α-allyl-phenylalanine methyl ester
• 英文别名: methyl (2S)-2-benzyl-2-(prop-2-enoxycarbonylamino)pent-4-enoate
• CAS: 501380-80-9
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: JCKUSYNZFZLALI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-allyloxycarbonyl-α-allyl-phenylalanine methyl ester 在 甲醇 、 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R)-N-(tert-butoxycarbonyl)-α-formylmethyl-phenylalanine 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
• 作为产物：
  描述：

  Allyl (2s,4s)-4-allyl-4-benzyl-2-tert-butyl-5-oxooxazolidine-3-carboxylate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-N-allyloxycarbonyl-α-allyl-phenylalanine 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

• 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.