1-benzyl-3-[(2S)-3-benzyloxy-2-(tritylamino)propionyl]-1,3-dihydro-indol-2-one | 1007843-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-benzyl-3-[(2S)-3-benzyloxy-2-(tritylamino)propionyl]-1,3-dihydro-indol-2-one
• 英文别名: 1-benzyl-3-[(2S)-3-phenylmethoxy-2-(tritylamino)propanoyl]-3H-indol-2-one
• CAS: 1007843-09-5
• 化学式: C₄₄H₃₈N₂O₃
• 分子量: 642.797
• InChiKey: IMNIRPHVGHBNKX-JFKYFZFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-[(2S)-3-benzyloxy-2-(tritylamino)propionyl]-1,3-dihydro-indol-2-one 、 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 、 氯仿 为溶剂， 反应 24.25h， 以62%的产率得到benzyl (2S)-3-[3-[(3S)-1-benzyl-2-oxo-3-[(2S)-3-phenylmethoxy-2-(tritylamino)propanoyl]indol-3-yl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments

  摘要：

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.

  DOI：

  10.1021/ol8014336
• 作为产物：
  描述：

  1-苄基-3H-吲哚-2-酮 、 Tr-Ser(OBn)-Im 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以50%的产率得到1-benzyl-3-[(2S)-3-benzyloxy-2-(tritylamino)propionyl]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid

  摘要：

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.

  DOI：

  10.1021/ol7025922

文献信息

• Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid
  作者：Brian S. Gerstenberger、Jinzhen Lin、Yvette S. Mimieux、Lauren E. Brown、Allen G. Oliver、Joseph P. Konopelski

  DOI：10.1021/ol7025922

  日期：2008.2.1

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.
• Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments
  作者：Jinzhen Lin、Brian S. Gerstenberger、Nhu Y T. Stessman、Joseph P. Konopelski

  DOI：10.1021/ol8014336

  日期：2008.9.18

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.