1,1-dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate | 452305-62-3

• 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: 1,1-dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
• 英文别名: tert-butyl N-[(1S)-1-[6-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-2-hydroxyethyl]carbamate
• CAS: 452305-62-3
• 化学式: C₂₂H₂₅BrN₂O₅S
• 分子量: 509.421
• InChiKey: NTWNIKCTAAJCOB-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate 在 4-二甲氨基吡啶 、 sodium azide 、 三丁基膦 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 三氟乙酸 为溶剂， 反应 33.0h， 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：

  氨基甲酸叔丁酯 、 N-tosyl-6-bromo-3-vinylindole 在 potassium dioxotetrahydroxoosmate(VI) sodium hydroxide 、 Hydroquinone 1,4-phthalazinediyl diether 、 次氯酸叔丁酯 作用下， 以 丙醇 、 水 为溶剂， 反应 3.0h， 生成 1,1-dimethylethyl (1R)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate 、 1,1-dimethylethyl (1R)-N-[2-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate 、 1,1-dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate 、 1,1-dimethylethyl (1S)-N-[2-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
  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.