(S)-2-Benzyloxycarbonylamino-5-methyl-2-naphthalen-2-ylmethyl-hex-4-enoic acid methyl ester | 847020-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-Benzyloxycarbonylamino-5-methyl-2-naphthalen-2-ylmethyl-hex-4-enoic acid methyl ester
• CAS: 847020-75-1
• 化学式: C₂₇H₂₉NO₄
• 分子量: 431.532
• InChiKey: MRHAPPGTWLURFI-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-5-methyl-2-naphthalen-2-ylmethyl-hex-4-enoic acid methyl ester 在 palladium on activated charcoal 四氧化锇 、 氢气 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 叔丁醇 为溶剂， 反应 6.5h， 生成 methyl (2R)-2-amino-4,4-dimethoxy-2-(naphthalen-2-ylmethyl)butanoate
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  (S)-2-Allyloxycarbonylamino-5-methyl-2-naphthalen-2-ylmethyl-hex-4-enoic acid 在 四(三苯基膦)钯 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-2-Benzyloxycarbonylamino-5-methyl-2-naphthalen-2-ylmethyl-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974