(S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester | 87113-91-5

• 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: (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester
• 英文别名: N-(1-adamantylacetyl)-L-proline benzyl ester；benzyl (2S)-1-[2-(1-adamantyl)acetyl]pyrrolidine-2-carboxylate
• CAS: 87113-91-5
• 化学式: C₂₄H₃₁NO₃
• 分子量: 381.515
• InChiKey: MGLBROJRXJWPLP-PQCJFMQRSA-N

物化性质

• 沸点：
  533.2±43.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester 在 palladium on activated charcoal N-乙基马来酰亚胺 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N-(1-adamantylacetyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester
  参考文献：
  名称：

  Tri- and tetrapeptide analogs of kinins as potential renal vasodilators

  摘要：

  Tri- and tetrapeptide analogues were synthesized and evaluated as renal vasodilators. These peptides were prepared by standard coupling reactions, which also provided good yields with hindered alpha-methyl amino acid derivatives. Preliminary evidence of renal vasodilator activity was determined in anesthetized dogs by measuring the effects on renal blood flow and calculating the accompanying changes in renal vascular resistance. The most potent compounds contained, in their basic structure, the L-prolyl-DL-alpha-methylphenylalanyl-L-arginine and L-prolyl-DL-alpha-methylphenylalanylglycyl-L-proline arrays. Substitution on the N-terminal proline with 4-phenylbutyryl and 4-(4-hydroxyphenyl)butyryl side chains produced enhanced renal vasodilator activity and, in certain cases, selectivity for the renal vasculature.

  DOI：

  10.1021/jm00369a017
• 作为产物：
  描述：

  L-脯氨酸苄酯盐酸盐 、 1-金刚烷乙酸 在 N-乙基马来酰亚胺 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Tri- and tetrapeptide analogs of kinins as potential renal vasodilators

  摘要：

  Tri- and tetrapeptide analogues were synthesized and evaluated as renal vasodilators. These peptides were prepared by standard coupling reactions, which also provided good yields with hindered alpha-methyl amino acid derivatives. Preliminary evidence of renal vasodilator activity was determined in anesthetized dogs by measuring the effects on renal blood flow and calculating the accompanying changes in renal vascular resistance. The most potent compounds contained, in their basic structure, the L-prolyl-DL-alpha-methylphenylalanyl-L-arginine and L-prolyl-DL-alpha-methylphenylalanylglycyl-L-proline arrays. Substitution on the N-terminal proline with 4-phenylbutyryl and 4-(4-hydroxyphenyl)butyryl side chains produced enhanced renal vasodilator activity and, in certain cases, selectivity for the renal vasculature.

  DOI：

  10.1021/jm00369a017

文献信息

• PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation
  作者：Eric Valeur、Mark Bradley

  DOI：10.1016/j.tet.2007.06.019

  日期：2007.9

  Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and

  由Merrifield树脂分三步合成了聚合物支撑的偶联剂聚苯乙烯-IIDQ，总转化率为86％。该试剂以高收率和高纯度将羧酸有效地偶联到胺上，不需要预活化步骤，并且可以耐受试剂添加的顺序。观察到PS-IIDQ比聚合物负载的碳二亚胺（PS-EDC和PS-DCC）更有效，并且在一般的酰胺键形成（包括苯胺和受阻底物偶联）方面，其收率高于HATU。用五种羧酸和九种胺（包括苯胺和仲胺）进行评估时，PS-IIDQ的平均分离收率为73％。
• PFEIFFER, F. R.
  作者：PFEIFFER, F. R.

  DOI：——

  日期：——
• US4387049A
  申请人：——

  公开号：US4387049A

  公开（公告）日：1983-06-07
• US4448972A
  申请人：——

  公开号：US4448972A

  公开（公告）日：1984-05-15