tert-butyl (2S)-N-tert-butoxycarbonyl-2-((4R)-2,3,4,5-tetrahydropyridazin-3-on-4-yl)glycinate | 449153-24-6

• 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: tert-butyl (2S)-N-tert-butoxycarbonyl-2-((4R)-2,3,4,5-tetrahydropyridazin-3-on-4-yl)glycinate
• 英文别名: tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(5R)-6-oxo-4,5-dihydro-1H-pyridazin-5-yl]acetate
• CAS: 449153-24-6
• 化学式: C₁₅H₂₅N₃O₅
• 分子量: 327.381
• InChiKey: ZOVOQQIPXGPNAD-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-N-tert-butoxycarbonyl-2-((4R)-2,3,4,5-tetrahydropyridazin-3-on-4-yl)glycinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-Amino-((R)-3-oxo-2,3,4,5-tetrahydro-pyridazin-4-yl)-acetic acid
  参考文献：
  名称：

  Versatile synthesis of ibotenic acid analogues with potential for activity at glutamate receptors by use of a homochiral β-lactam template in our ‘ring switching’ strategy

  摘要：

  The activated eta-lactam aldehydes 31 and 55 were synthesised and found to be excellent substrate for our 'ring switching' strategy for preparation of libraries of homochiral compounds with potential for activity at specific glutamate receptor sub-types. The product heteroaromatic glycine derivatives were ibotenate analogues and the beta-lactam templates proved to be more versatile than the previously used pyroglutamic templates. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00590-7
• 作为产物：
  描述：

  tert-butyl (3R,4S)-N-tert-butoxycarbonyl-3-oxoethylazetidin-2-one-4-carboxylate 在 一水合肼 作用下， 以 苯 为溶剂， 反应 24.0h， 以203 mg的产率得到tert-butyl (2S)-N-tert-butoxycarbonyl-2-((4R)-2,3,4,5-tetrahydropyridazin-3-on-4-yl)glycinate
  参考文献：
  名称：

  β-Lactams as versatile synthons for homochiral ibotenate analogues with potential for activity at glutamate receptors1

  摘要：

  我们合成了活化的δ-内酰胺醛 37、41 和 57。与焦谷氨酸或 6-oxopipecolinate 系列中的相应化合物相比，醛 37 和 57 被证明是我们的 "环转 "策略中同手性谷氨酸拮抗剂的通用底物。从这些醛类化合物中制备出了大量在特定谷氨酸受体亚型上具有潜在活性的同手性杂芳香族甘氨酸衍生物库。醛 41 含有一个额外的阴离子稳定基团，在 "环状切换 "条件下进行了逆醛化过程。

  DOI：

  10.1039/b304607a

文献信息

• Versatile synthesis of ibotenic acid analogues with potential for activity at glutamate receptors by use of a homochiral β-lactam template in our ‘ring switching’ strategy
  作者：Konstantinos Papadopoulos、Douglas W Young

  DOI：10.1016/s0040-4039(02)00590-7

  日期：2002.5

  The activated eta-lactam aldehydes 31 and 55 were synthesised and found to be excellent substrate for our 'ring switching' strategy for preparation of libraries of homochiral compounds with potential for activity at specific glutamate receptor sub-types. The product heteroaromatic glycine derivatives were ibotenate analogues and the beta-lactam templates proved to be more versatile than the previously used pyroglutamic templates. (C) 2002 Published by Elsevier Science Ltd.
• β-Lactams as versatile synthons for homochiral ibotenate analogues with potential for activity at glutamate receptors1
  作者：Peter B. Hitchcock、Konstantinos Papadopoulos、Douglas W. Young

  DOI：10.1039/b304607a

  日期：——

  The activated β-lactam aldehydes 37, 41 and 57 were synthesised. Aldehydes 37 and 57 proved to be more versatile substrates for our “ring switching” strategy to homochiral glutamate antagonists than the corresponding compounds in the pyroglutamate or 6-oxopipecolinate series had been. Substantial libraries of homochiral heteroaromatic glycine derivatives with potential for activity at specific glutamate receptor sub-types were prepared from these aldehydes. The aldehyde 41, containing an additional anion stabilising group, underwent a retro-aldol process under “ring switching” conditions.

  我们合成了活化的δ-内酰胺醛 37、41 和 57。与焦谷氨酸或 6-oxopipecolinate 系列中的相应化合物相比，醛 37 和 57 被证明是我们的 "环转 "策略中同手性谷氨酸拮抗剂的通用底物。从这些醛类化合物中制备出了大量在特定谷氨酸受体亚型上具有潜在活性的同手性杂芳香族甘氨酸衍生物库。醛 41 含有一个额外的阴离子稳定基团，在 "环状切换 "条件下进行了逆醛化过程。