(3R,6S,8aR)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-2,3,6,7,8,8a-hexahydropyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid | 150852-39-4

• 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: (3R,6S,8aR)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-2,3,6,7,8,8a-hexahydropyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid
• CAS: 150852-39-4
• 化学式: C₁₃H₂₀N₂O₆
• 分子量: 300.312
• InChiKey: AEQMMOBDRXTUTB-HRDYMLBCSA-N

物化性质

• 沸点：
  537.6±50.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,6S,8aR)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-2,3,6,7,8,8a-hexahydropyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid 在 二苯基膦叠氮化物 作用下， 生成 (3R,6S,8aR)-3-[2-(2,4-Dinitro-phenylamino)-acetylamino]-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid [(4-nitro-phenylcarbamoyl)-methyl]-amide
  参考文献：
  名称：

  Synthesis of potential β-turn bicyclic dipeptide mimetics

  摘要：

  描述了四种非对映异构双环内酰胺的合成，旨在

  DOI：

  10.1039/c39930000935
• 作为产物：
  描述：

  N-Boc-O-苄基-D-丝氨酸 在 三氟乙酸 lithium hydroxide 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (3R,6S,8aR)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-2,3,6,7,8,8a-hexahydropyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid
  参考文献：
  名称：

  A convenient and versatile synthesis of 6,5- and 7,5-fused bicyclic lactams as peptidomimetics

  摘要：

  Chemo-selective reduction of the pyroglutamate ring carbonyl in a serine-pyroglutamate or homoserine to pyroglutamate dipeptide gave a hemiaminal. Treatment of the hemiaminal with a catalytic amount of TFA in CH,CI, generated an N-acyliminium ion that was intramolecularly trapped by the side-chain hydroxyl to give a 6.5 or 7,5-bicyclic lactam. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00909-1

文献信息

• A convenient and versatile synthesis of 6,5- and 7,5-fused bicyclic lactams as peptidomimetics
  作者：Xiaojun Zhang、Wen Jiang、Aaron C. Schmitt

  DOI：10.1016/s0040-4039(01)00909-1

  日期：2001.7

  Chemo-selective reduction of the pyroglutamate ring carbonyl in a serine-pyroglutamate or homoserine to pyroglutamate dipeptide gave a hemiaminal. Treatment of the hemiaminal with a catalytic amount of TFA in CH,CI, generated an N-acyliminium ion that was intramolecularly trapped by the side-chain hydroxyl to give a 6.5 or 7,5-bicyclic lactam. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of potential β-turn bicyclic dipeptide mimetics
  作者：Jack E. Baldwin、Christopher Hulme、Christopher J. Schofield、Alison J. Edwards

  DOI：10.1039/c39930000935

  日期：——

  The syntheses of four diastereoisomeric bicyclic lactams, intended for analysis as β-turn-inducing mimetics, are described; the crystal structure of one derivative has been reported.

  描述了四种非对映异构双环内酰胺的合成，旨在