(3S,6R)-3-Allyl-5-ethoxy-3-ethyl-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one | 204272-88-8

• 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: (3S,6R)-3-Allyl-5-ethoxy-3-ethyl-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one
• 英文别名: (2R,5S)-3-ethoxy-5-ethyl-2-methyl-1-[(1S)-1-phenylethyl]-5-prop-2-enyl-2H-pyrazin-6-one
• CAS: 204272-88-8
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: KXMCWRMNAJHMRI-YRNRMSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,6R)-3-Allyl-5-ethoxy-3-ethyl-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one 在 盐酸 、 氨 、 sodium 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 3.08h， 生成 (R)-2-((S)-2-Amino-2-ethyl-pent-4-enoylamino)-propionic acid ethyl ester; hydrochloride
  参考文献：
  名称：

  Stereoselective synthesis of sterically constrained dipeptides. Part 2

  摘要：

  The alkylation of the diastereomeric mixture of lactims 2 and 3 occurs in total regioselectivity and good to high facial stereoselectivity (d.s. ranging from 82 to 97%). Cleavage of the lactim 4e gives enantiomerically pure dipeptide 12, sterically constrained at the alpha-carbon. The absolute configuration of the new stereocentres has been assigned on the basis of H-1-NMR data and NOE measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00609-5
• 作为产物：
  描述：

  丙烯酰碘 、 (R)-5-Ethoxy-3-ethyl-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one 在 lithium hexamethyldisilazane 作用下， 生成 (3S,6R)-3-Allyl-5-ethoxy-3-ethyl-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one 、 (3R,6R)-3-Allyl-5-ethoxy-3-ethyl-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of sterically constrained dipeptides. Part 2

  摘要：

  The alkylation of the diastereomeric mixture of lactims 2 and 3 occurs in total regioselectivity and good to high facial stereoselectivity (d.s. ranging from 82 to 97%). Cleavage of the lactim 4e gives enantiomerically pure dipeptide 12, sterically constrained at the alpha-carbon. The absolute configuration of the new stereocentres has been assigned on the basis of H-1-NMR data and NOE measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00609-5

文献信息

• Stereoselective synthesis of sterically constrained dipeptides. Part 2
  作者：Gianni Porzi、Sergio Sandri、Piera Verrocchio

  DOI：10.1016/s0957-4166(97)00609-5

  日期：1998.1

  The alkylation of the diastereomeric mixture of lactims 2 and 3 occurs in total regioselectivity and good to high facial stereoselectivity (d.s. ranging from 82 to 97%). Cleavage of the lactim 4e gives enantiomerically pure dipeptide 12, sterically constrained at the alpha-carbon. The absolute configuration of the new stereocentres has been assigned on the basis of H-1-NMR data and NOE measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.