(S)-3-(6-bromo-1H-indol-3-yl)-6-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-5,6-dihydro-1H-pyrazin-2-one | 452305-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-(6-bromo-1H-indol-3-yl)-6-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-5,6-dihydro-1H-pyrazin-2-one
• 英文别名: (2S)-5-(6-bromo-1H-indol-3-yl)-2-[6-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-2,3-dihydro-1H-pyrazin-6-one
• CAS: 452305-69-0
• 化学式: C₂₇H₂₀Br₂N₄O₃S
• 分子量: 640.355
• InChiKey: XAAGAWLEGUCJIK-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(6-bromo-1H-indol-3-yl)-6-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-5,6-dihydro-1H-pyrazin-2-one 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 6.0h， 生成 (6S)-3-[6-bromo-1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5,6-dihydro-1-methyl-1H-pyrazin-2-one
  参考文献：
  名称：

  Asymmetric aminohydroxylation of vinyl indoles: a short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A

  摘要：

  A useful approach for the direct enantioselective synthesis of (S)-N-boc-protected alpha-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%, is described. Expeditious enantioselective syntheses of hamacanthin A and dragmacidin A have been achieved using the corresponding N-Boc-protected alpha-6-bromo-indol-3-ylglycinol as the key intermediate. Furthermore, the absolute stereochemistry of cis- and trans-dihydrohamacanthin A has been determined through the enantioselective total synthesis of the unnatural enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00111-8
• 作为产物：
  描述：

  2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride 在 三丁基膦 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.0h， 生成 (S)-3-(6-bromo-1H-indol-3-yl)-6-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-5,6-dihydro-1H-pyrazin-2-one
  参考文献：
  名称：

  Asymmetric aminohydroxylation of vinyl indoles: a short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A

  摘要：

  A useful approach for the direct enantioselective synthesis of (S)-N-boc-protected alpha-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%, is described. Expeditious enantioselective syntheses of hamacanthin A and dragmacidin A have been achieved using the corresponding N-Boc-protected alpha-6-bromo-indol-3-ylglycinol as the key intermediate. Furthermore, the absolute stereochemistry of cis- and trans-dihydrohamacanthin A has been determined through the enantioselective total synthesis of the unnatural enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00111-8

文献信息

• Asymmetric aminohydroxylation of vinyl indoles: a short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A
  作者：Cai-Guang Yang、Jun Wang、Xiao-Xia Tang、Biao Jiang

  DOI：10.1016/s0957-4166(02)00111-8

  日期：2002.3

  A useful approach for the direct enantioselective synthesis of (S)-N-boc-protected alpha-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%, is described. Expeditious enantioselective syntheses of hamacanthin A and dragmacidin A have been achieved using the corresponding N-Boc-protected alpha-6-bromo-indol-3-ylglycinol as the key intermediate. Furthermore, the absolute stereochemistry of cis- and trans-dihydrohamacanthin A has been determined through the enantioselective total synthesis of the unnatural enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.