(S)-N-(tert-butoxycarbonyl)-α-allyl-phenylalanine methyl ester | 143140-35-6

• 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-(tert-butoxycarbonyl)-α-allyl-phenylalanine methyl ester
• 英文别名: methyl (2S)-2-benzyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoate
• CAS: 143140-35-6
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: VWKVFUKKQTYTLP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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-(tert-butoxycarbonyl)-α-allyl-phenylalanine methyl ester 在 甲醇 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以80%的产率得到(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：

  (2S,3R)-N-叔丁氧羰基-2,3-二苯基吗啉-6-酮 在 氨 、 sodium hexamethyldisilazane 、 氢气 、 lithium 作用下， 生成 (S)-N-(tert-butoxycarbonyl)-α-allyl-phenylalanine methyl ester
  参考文献：
  名称：

  Baldwin, Jack E.; Lee, Victor; Schofield, Christopher J., Heterocycles, 1992, vol. 34, # 5, p. 903 - 906

  摘要：

  DOI：

文献信息

• Baldwin, Jack E.; Lee, Victor; Schofield, Christopher J., Heterocycles, 1992, vol. 34, # 5, p. 903 - 906
  作者：Baldwin, Jack E.、Lee, Victor、Schofield, Christopher J.

  DOI：——

  日期：——
• 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.