2,3-dibromo-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid | 935659-21-5

• 分子结构分类: 有机化合物
• 英文名称: 2,3-dibromo-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid
• CAS: 935659-21-5
• 化学式: C₁₈H₁₅Br₂NO₄S
• 分子量: 501.195
• InChiKey: UESSZOZDSWNUEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.37
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-dibromo-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(Z)-3-(2-bromovinyl)-1-tosyl-1H-indole
  参考文献：
  名称：

  Highly Efficient and Stereoselective N-Vinylation of Oxiranecarboxamides and Unprecedented 8-endo-Epoxy-arene Cyclization:  Expedient and Biomimetic Synthesis of Some Clausena Alkaloids

  摘要：

  Catalyzed by CuI/N,N-dimethylglycine, oxiranecarboxamides underwent a highly efficient and stereoselective N-vinylation reaction with (Z)-1-aryl-2-bromoethenes to afford the corresponding enamides. The method has been applied to a straightforward synthesis of (-)-(2R,3S)-SB204900, the enantiomer of the natural product. Following a hypothetic biomimetic pathway, both (+)-(5R,6S)-xi-Clausenamide and (-)-(5R,6S)-balasubramide have been efficiently synthesized for the first time through the unprecedented intramolecular 8-endo-epoxy-arene cyclization of (Z)-N-(phenylvinyl)oxiranecarboxamides.

  DOI：

  10.1021/ol070292+
• 作为产物：
  描述：

  (2E)-3-{1-[(4-甲基苯基)磺酰基]-1H-吲哚-3-基}丙烯酸 在 溴 作用下， 以 氯仿 为溶剂， 以100%的产率得到2,3-dibromo-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid
  参考文献：
  名称：

  Highly Efficient and Stereoselective N-Vinylation of Oxiranecarboxamides and Unprecedented 8-endo-Epoxy-arene Cyclization:  Expedient and Biomimetic Synthesis of Some Clausena Alkaloids

  摘要：

  Catalyzed by CuI/N,N-dimethylglycine, oxiranecarboxamides underwent a highly efficient and stereoselective N-vinylation reaction with (Z)-1-aryl-2-bromoethenes to afford the corresponding enamides. The method has been applied to a straightforward synthesis of (-)-(2R,3S)-SB204900, the enantiomer of the natural product. Following a hypothetic biomimetic pathway, both (+)-(5R,6S)-xi-Clausenamide and (-)-(5R,6S)-balasubramide have been efficiently synthesized for the first time through the unprecedented intramolecular 8-endo-epoxy-arene cyclization of (Z)-N-(phenylvinyl)oxiranecarboxamides.

  DOI：

  10.1021/ol070292+