(2SR,4RS,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-1,4-octanolactone | 628318-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2SR,4RS,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-1,4-octanolactone
• CAS: 628318-85-4
• 化学式: C₁₅H₂₄N₂O₄
• 分子量: 296.367
• InChiKey: OZWUWFHNEGRWJU-CXQJBGSLSA-N

物化性质

• 沸点：
  484.6±30.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.42
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2SR,4RS,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-1,4-octanolactone 在 platinum(IV) oxide 氢气 、 tin(II) acetate 、 三氧化硫吡啶 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 169.0h， 生成 N-[(2SR,5S)-2-[N-benzyloxycarbonylamino-L-threonylaminomethyl]-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-7-methyloctanoyl]-L-leucinamide
  参考文献：
  名称：

  Synthesis and Evaluation of Macrocyclic Transition State Analogue Inhibitors for α-Chymotrypsin

  摘要：

  Lactams 1 and 2 are readily formed from acyclic precursors in the presence of trypsin and chymotrypsin, respectively, identifying the macrocyclic ring system as a potential motif for constrained transition state analogue inhibitors of the serine peptidases. Ketone 3 was synthesized and shown to be a modest inhibitor of chymotrypsin (K-i = 220 muM), albeit 4-fold more potent than the acyclic hydroxy acid 25 (K-i = 1.5 mM as a mixture of epimers). A precursor (31) to the amino boronic acid 4 was also prepared; although this derivative was a potent inhibitor of chymotrypsin (K-i = 130 nM) by virtue of the boronic acid moiety, it showed no advantage over the des-amino analogue 32 (K-i = 120 nM), which is not capable of cyclizing.

  DOI：

  10.1021/jo034837z
• 作为产物：
  描述：

  methyl (2SR,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-4-oxooctanoate 在 sodium tetrahydroborate 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 乙二醇甲醚 、 二氯甲烷 为溶剂， 反应 24.33h， 以51%的产率得到(2SR,4RS,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-1,4-octanolactone
  参考文献：
  名称：

  Synthesis and Evaluation of Macrocyclic Transition State Analogue Inhibitors for α-Chymotrypsin

  摘要：

  Lactams 1 and 2 are readily formed from acyclic precursors in the presence of trypsin and chymotrypsin, respectively, identifying the macrocyclic ring system as a potential motif for constrained transition state analogue inhibitors of the serine peptidases. Ketone 3 was synthesized and shown to be a modest inhibitor of chymotrypsin (K-i = 220 muM), albeit 4-fold more potent than the acyclic hydroxy acid 25 (K-i = 1.5 mM as a mixture of epimers). A precursor (31) to the amino boronic acid 4 was also prepared; although this derivative was a potent inhibitor of chymotrypsin (K-i = 130 nM) by virtue of the boronic acid moiety, it showed no advantage over the des-amino analogue 32 (K-i = 120 nM), which is not capable of cyclizing.

  DOI：

  10.1021/jo034837z