(3S,6S)-3,6-Bis-(6-bromo-1H-indol-3-yl)-piperazine-2,5-dione

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,6S)-3,6-Bis-(6-bromo-1H-indol-3-yl)-piperazine-2,5-dione
• 英文别名: (3S,6S)-3,6-bis(6-bromo-1H-indol-3-yl)piperazine-2,5-dione
• 化学式: C₂₀H₁₄Br₂N₄O₂
• 分子量: 502.165
• InChiKey: ODRKYJVSPNBJMV-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3,6-Bis-(6-bromo-1H-indol-3-yl)-piperazine-2,5-dione 在 硼烷四氢呋喃络合物 作用下， 以20%的产率得到cis-2,5-bis(6'-bromo-3'-indolyl)piperazine
  参考文献：
  名称：

  Syntheses of bis(indolyl)-piperazine alkaloids, dragmacidin B and C, and dihydrohamacanthin A

  摘要：

  The syntheses of trans- and cis-isomers of dragmacidin C and 3,4-dihydrohamacanthin A, and dragmacidin B have been accomplished by condensation of two indolylglycines followed by cyclization and reduction. The relative stereochemistry of dragmacidin C was confirmed to be cis, which is distinct from that of other dragmacidins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00771-2
• 作为产物：
  描述：

  Prop-2-enyl 2-(1-acetyl-6-bromoindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate 在 甲酸 、 RhCl(PPh₃)3 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (3S,6S)-3,6-Bis-(6-bromo-1H-indol-3-yl)-piperazine-2,5-dione
  参考文献：
  名称：

  Syntheses of bis(indolyl)-piperazine alkaloids, dragmacidin B and C, and dihydrohamacanthin A

  摘要：

  The syntheses of trans- and cis-isomers of dragmacidin C and 3,4-dihydrohamacanthin A, and dragmacidin B have been accomplished by condensation of two indolylglycines followed by cyclization and reduction. The relative stereochemistry of dragmacidin C was confirmed to be cis, which is distinct from that of other dragmacidins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00771-2

文献信息

• Syntheses of bis(indolyl)-piperazine alkaloids, dragmacidin B and C, and dihydrohamacanthin A
  作者：Tomomi Kawasaki、Kohsuke Ohno、Hidetaka Enoki、Yasuko Umemoto、Masanori Sakamoto

  DOI：10.1016/s0040-4039(02)00771-2

  日期：2002.6

  The syntheses of trans- and cis-isomers of dragmacidin C and 3,4-dihydrohamacanthin A, and dragmacidin B have been accomplished by condensation of two indolylglycines followed by cyclization and reduction. The relative stereochemistry of dragmacidin C was confirmed to be cis, which is distinct from that of other dragmacidins. (C) 2002 Elsevier Science Ltd. All rights reserved.