(8S,10S)-8-(2-Bromo-2-fluoro-acetyl)-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione | 444910-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: (8S,10S)-8-(2-Bromo-2-fluoro-acetyl)-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione
• 英文别名: (7S,9S)-9-(2-bromo-2-fluoroacetyl)-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 444910-63-8
• 化学式: C₂₁H₁₆BrFO₈
• 分子量: 495.256
• InChiKey: BGVKZPXKPSAGGX-RUFKVZNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (8S,10S)-8-(2-Bromo-2-fluoro-acetyl)-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione 在 silver tetrafluoroborate 作用下， 以 二甲基亚砜 为溶剂， 以95%的产率得到(8S,10S)-8-(2-Fluoro-2-hydroxy-acetyl)-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione
  参考文献：
  名称：

  Synthesis of 14-fluorodoxorubicin

  摘要：

  Abstraet-Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00299-x
• 作为产物：
  描述：

  (2S,4S)-(+)-2-fluoroacetyl-2,4,5,11-tetrahydroxy-7-methoxy-1,2,3,4-tetrahydro-6,11-naphthacenedione 在 pyridinium hydrobromide perbromide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(8S,10S)-8-(2-Bromo-2-fluoro-acetyl)-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione
  参考文献：
  名称：

  Synthesis of 14-fluorodoxorubicin

  摘要：

  Abstraet-Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00299-x

文献信息

• Synthesis of 14-fluorodoxorubicin
  作者：M. Berettoni、A. Cipollone、L. Olivieri、D. Palomba、F. Arcamone、C.A. Maggi、F. Animati

  DOI：10.1016/s0040-4039(02)00299-x

  日期：2002.4

  Abstraet-Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system. (C) 2002 Elsevier Science Ltd. All rights reserved.