(3R,6S,8R,8aR)-3-tert-Butoxycarbonylamino-4-oxo-8-(3-phenyl-propyl)-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid ethyl ester | 363599-68-2

• 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: (3R,6S,8R,8aR)-3-tert-Butoxycarbonylamino-4-oxo-8-(3-phenyl-propyl)-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid ethyl ester
• 英文别名: ethyl (3R,6S,8R,8aR)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-8-(3-phenylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[2,1-b][1,3]oxazine-6-carboxylate
• CAS: 363599-68-2
• 化学式: C₂₄H₃₄N₂O₆
• 分子量: 446.544
• InChiKey: IEOGTUKUDCCDGX-WERVVEIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,6S,8R,8aR)-3-tert-Butoxycarbonylamino-4-oxo-8-(3-phenyl-propyl)-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以100%的产率得到(3R,6S,8R,8aR)-3-tert-Butoxycarbonylamino-4-oxo-8-(3-phenyl-propyl)-hexahydro-pyrrolo[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
• 作为产物：
  描述：

  BOC-L-焦谷氨酸乙酯 在 palladium on activated charcoal 、 三氟乙酸 氢气 、 三乙基硼氢化锂 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R,6S,8R,8aR)-3-tert-Butoxycarbonylamino-4-oxo-8-(3-phenyl-propyl)-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid ethyl ester
  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