(S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester | 187087-44-1

• 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-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
• 英文别名: (1R,2S,3R,4S)-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-1-carbonyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS: 187087-44-1
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: ULDZHRYGFBWNMU-HTOAHKCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (1S,2S,3R,4R)-3-((S)-2-Hydroxycarbamoyl-pyrrolidine-1-carbonyl)-bicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  ACE抑制剂Idrapril构象受限类似物的合成

  摘要：

  ACE抑制剂Idrapril的受构象约束的类似物3已经通过五步合成法制备。合成中的关键步骤是通过与叔丁基（S）-脯氨酸酯反应来脱去内-降冰片烯5-烯-2,3-二羧酸酐4。

  DOI：

  10.1016/s0040-4020(98)01033-3
• 作为产物：
  描述：

  L-脯氨酸叔丁酯 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 以 二氯甲烷 为溶剂， 反应 18.0h， 以57%的产率得到(S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Peptides and Pseudopeptides Incorporating an endo-(2S,3R)-Norborn-5-ene Residue as a Turn Inducer

  摘要：

  The desymmetrization of endo-norborn-5-ene-2,3-dicarboxylic anhydride (5) by proline derivatives is used to prepare peptides and pseudopeptides incorporating an endo-(2S,3R)-2-amino-3-carboxynorborn-5-ene (1) residue. The peptides contain a single conformationally constrained beta-amino acid residue, while the pseudopeptides also contain a urea linkage and two peptide chains running in parallel directions. The key step in the synthesis is a Curtius rearrangement on the amido acids 6a,b to generate an isocyanate that is then directly reacted with suitably protected amino acids and peptides to give the peptides and pseudopeptides. The synthesis of the peptide analogue 4 is also described; in this compound, the two peptide chains run parallel to one another, and the stereochemistry of the norbornene unit within compound 4 was determined by X-ray analysis of the related peptide analogue 23.

  DOI：

  10.1021/jo9717651

文献信息

• The Synthesis of Conformationally Constrained Peptides and <i>Pseudo</i>-Peptides Incorporating an <i>Endo</i>-(2<i>S</i>,3<i>R</i>)-2-Amino-3-Carboxy-Norborn-5-ene Residue
  作者：Iwan Jones、Wyn Jones、Michael North

  DOI：10.1055/s-1997-706

  日期：——

  Methodology has been developed to carry out a Curtius rearrangement on enantiomerically pure amido-acids derived from (S)-proline esters. The resulting isocyanates were used to prepare conformationally constrained peptides incorporating and endo-(2S,3R)-2-amino-3-carboxy-norborn-5-ene residue.

  已经开发出一种方法来对源自(S)-脯氨酸酯的对称纯氨基酸进行Curtius重排。所得到的异氰酸酯被用于制备包含内源性(2S,3R)-2-氨基-3-羧基-诺喹烯残基的构象受限肽。
• Synthesis of Peptides and Pseudopeptides Incorporating an <i>endo-</i>(2<i>S</i>,3<i>R</i>)-Norborn-5-ene Residue as a Turn Inducer
  作者：David E. Hibbs、Michael B. Hursthouse、Iwan G. Jones、Wyn Jones、K. M. Abdul Malik、Michael North

  DOI：10.1021/jo9717651

  日期：1998.3.1

  The desymmetrization of endo-norborn-5-ene-2,3-dicarboxylic anhydride (5) by proline derivatives is used to prepare peptides and pseudopeptides incorporating an endo-(2S,3R)-2-amino-3-carboxynorborn-5-ene (1) residue. The peptides contain a single conformationally constrained beta-amino acid residue, while the pseudopeptides also contain a urea linkage and two peptide chains running in parallel directions. The key step in the synthesis is a Curtius rearrangement on the amido acids 6a,b to generate an isocyanate that is then directly reacted with suitably protected amino acids and peptides to give the peptides and pseudopeptides. The synthesis of the peptide analogue 4 is also described; in this compound, the two peptide chains run parallel to one another, and the stereochemistry of the norbornene unit within compound 4 was determined by X-ray analysis of the related peptide analogue 23.
• The synthesis of conformationally constrained analogues of the ACE inhibitor Idrapril
  作者：Iwan G Jones、Wyn Jones、Michael North

  DOI：10.1016/s0040-4020(98)01033-3

  日期：1999.1

  A conformationally constrained analogue 3 of the ACE inhibitor Idrapril has been prepared by a five-step synthesis. The key step in the synthesis is the desymmetrization of endo-norborn-5-ene-2,3-dicarboxylic anhydride 4 by reaction with t-butyl (S)-prolinate.

  ACE抑制剂Idrapril的受构象约束的类似物3已经通过五步合成法制备。合成中的关键步骤是通过与叔丁基（S）-脯氨酸酯反应来脱去内-降冰片烯5-烯-2,3-二羧酸酐4。