3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-(2,6-dichlorobenzyloxyphenyl))propanoyl]-5-oxazolidinone | 306775-54-2

• 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: 3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-(2,6-dichlorobenzyloxyphenyl))propanoyl]-5-oxazolidinone
• 英文别名: 2-[(2S)-3-[4-[(2,6-dichlorophenyl)methoxy]phenyl]-1-oxo-1-(5-oxo-1,3-oxazolidin-3-yl)propan-2-yl]isoindole-1,3-dione
• CAS: 306775-54-2
• 化学式: C₂₇H₂₀Cl₂N₂O₆
• 分子量: 539.372
• InChiKey: QXDKMLAEOUPYHX-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-(2,6-dichlorobenzyloxyphenyl))propanoyl]-5-oxazolidinone 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到4(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-benzazepin-2-acetic acid
  参考文献：
  名称：

  Efficient Synthesis of (S)-4-Phthalimido-1,3,4,5- tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-benzazepin-2-acetic Acid (Pht-Hba(2,6-Cl₂-Bn)-Gly-OH)¹

  摘要：

  4-Amino-2-benzazepin-3-ones have proven very useful for studying the biologically active conformations of peptides. The synthesis of Pht-Aba-Xaa-OH by reaction of the corresponding 1,3-oxazolidin-5-one with trifluoromethanesulfonic acid (TFMSA) has been reported in the literature. However, when this procedure was applied to the preparation of Pht-Hba(Bn)-Gly-OH 8, many byproducts were formed and the yield of the desired aminobenzazepinones 7 and 8 was very low. We report in this paper an efficient methodology for the synthesis of Pht-Hba(2,6-Cl-2-Bn)-Gly-OH 17 starting from the commercially available tyro sine. In our procedure, the dipeptide Pht-Tyr(2,6-Cl-2-Bn)-Gly-OH 15 is converted,to the 1,3-oxazolidin-5-one 16 Which then undergoes Friedel-Crafts cyclization in the presence of tin tetrachloride to afford the desired 4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-2-benzazepin-3-one 17 in excellent yield.

  DOI：

  10.1021/jo000530d
• 作为产物：
  描述：

  L-酪氨酸 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 对甲苯磺酸 、 copper(II) sulfate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 23.0h， 生成 3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-(2,6-dichlorobenzyloxyphenyl))propanoyl]-5-oxazolidinone
  参考文献：
  名称：

  Efficient Synthesis of (S)-4-Phthalimido-1,3,4,5- tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-benzazepin-2-acetic Acid (Pht-Hba(2,6-Cl₂-Bn)-Gly-OH)¹

  摘要：

  4-Amino-2-benzazepin-3-ones have proven very useful for studying the biologically active conformations of peptides. The synthesis of Pht-Aba-Xaa-OH by reaction of the corresponding 1,3-oxazolidin-5-one with trifluoromethanesulfonic acid (TFMSA) has been reported in the literature. However, when this procedure was applied to the preparation of Pht-Hba(Bn)-Gly-OH 8, many byproducts were formed and the yield of the desired aminobenzazepinones 7 and 8 was very low. We report in this paper an efficient methodology for the synthesis of Pht-Hba(2,6-Cl-2-Bn)-Gly-OH 17 starting from the commercially available tyro sine. In our procedure, the dipeptide Pht-Tyr(2,6-Cl-2-Bn)-Gly-OH 15 is converted,to the 1,3-oxazolidin-5-one 16 Which then undergoes Friedel-Crafts cyclization in the presence of tin tetrachloride to afford the desired 4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-2-benzazepin-3-one 17 in excellent yield.

  DOI：

  10.1021/jo000530d