7-溴-1-甲氧基甲基-1,2-二氢-吲哚-2-酮 | 1007843-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 7-溴-1-甲氧基甲基-1,2-二氢-吲哚-2-酮
• 英文名称: 7-bromo-1-methoxymethyl-1,2-dihydro-indol-2-one
• 英文别名: 7-bromo-1-(methoxymethyl)-3H-indol-2-one
• CAS: 1007843-07-3
• 化学式: C₁₀H₁₀BrNO₂
• 分子量: 256.099
• InChiKey: MAMDSGYSOKTDHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-溴-1-甲氧基甲基-1,2-二氢-吲哚-2-酮 、 Tr-Ser(OBn)-Im 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以72%的产率得到7-bromo-1-methoxymethyl-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
• 作为产物：
  描述：

  N-(2'-bromophenyl)-N-methoxymethyl-2-diazoacetamide 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以60%的产率得到7-溴-1-甲氧基甲基-1,2-二氢-吲哚-2-酮
  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

• 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.
• 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.