(6R,12S)-1-aza-3-(pyroglutamylamino)-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene | 325460-76-2

• 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: (6R,12S)-1-aza-3-(pyroglutamylamino)-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene
• 英文别名: (2S)-N-[(8aR)-8a-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-7-phenyl-1,2,3,8-tetrahydroindolizin-6-yl]-5-oxopyrrolidine-2-carboxamide
• CAS: 325460-76-2
• 化学式: C₂₆H₃₇N₃O₄Si
• 分子量: 483.683
• InChiKey: KMVXQSXAIQKRQL-RXFWQSSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  87.74
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6R,12S)-1-aza-3-(pyroglutamylamino)-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 在 重铬酸吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 硫酸 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.25h， 生成 (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carboxamoyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene
  参考文献：
  名称：

  Constrained Peptidomimetics for TRH: cis-Peptide Bond Analogs

  摘要：

  Two constrained analogs of the tripeptide hormone thyroliberin (TRH) have been synthesized. In both, the HisPro peptide bond of the hormone has been 'locked' into a cis-conformation. In the first analog, the constraint used was identical to the constraint used in an earlier trans-peptide bond analog that was a potent agonist for the TRH endocrine receptor TRH-R-1. The second analog was built in order to take advantage of a tetrazole ring as the cis-peptide bond constraint. Neither analog showed agonist or antagonist behavior toward TRH-R1 suggesting that the cis-peptide bond conformation may not play a role in the affinity of TRH for TRH-R1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00886-3
• 作为产物：
  描述：

  (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane 在 2,6-二甲基吡啶 、 氨 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 146.02h， 生成 (6R,12S)-1-aza-3-(pyroglutamylamino)-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene
  参考文献：
  名称：

  Constrained Peptidomimetics for TRH: cis-Peptide Bond Analogs

  摘要：

  Two constrained analogs of the tripeptide hormone thyroliberin (TRH) have been synthesized. In both, the HisPro peptide bond of the hormone has been 'locked' into a cis-conformation. In the first analog, the constraint used was identical to the constraint used in an earlier trans-peptide bond analog that was a potent agonist for the TRH endocrine receptor TRH-R-1. The second analog was built in order to take advantage of a tetrazole ring as the cis-peptide bond constraint. Neither analog showed agonist or antagonist behavior toward TRH-R1 suggesting that the cis-peptide bond conformation may not play a role in the affinity of TRH for TRH-R1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00886-3