(3aS,8R,9R,9aR,11aR,13aS,13bR,13cS)-13a-hydroxy-6,9a,14,14-tetramethyl-2,5-dioxo-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,9-diyl diacetate | 911285-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aS,8R,9R,9aR,11aR,13aS,13bR,13cS)-13a-hydroxy-6,9a,14,14-tetramethyl-2,5-dioxo-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,9-diyl diacetate
• CAS: 911285-66-0
• 化学式: C₂₅H₃₂O₁₀
• 分子量: 492.523
• InChiKey: ACJBWWAGHXXFAR-CENMLUABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  35.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3aS,8R,9R,9aR,11aR,13aS,13bR,13cS)-13a-hydroxy-6,9a,14,14-tetramethyl-2,5-dioxo-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,9-diyl diacetate 在 偶氮二异丁腈 、 溴 、 三正丁基氢锡 、 silver(I) acetate 作用下， 以 苯 为溶剂， 反应 0.33h， 生成 [(1S,5S,6R,13R,14R,15R)-14-acetyloxy-13,17,20,20-tetramethyl-3,7,18-trioxo-2,4,9-trioxatetracyclo[14.3.1.01,5.06,13]icos-16-en-15-yl] acetate
  参考文献：
  名称：

  Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid

  摘要：

  A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.080
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium acetate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 168.33h， 生成 (3aS,8R,9R,9aR,11aR,13aS,13bR,13cS)-13a-hydroxy-6,9a,14,14-tetramethyl-2,5-dioxo-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-3a,7-methanooxeto[2'',3'':5',6']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxole-8,9-diyl diacetate
  参考文献：
  名称：

  Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid

  摘要：

  A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.080

文献信息

• Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid
  作者：Zorana Ferjancic、Radomir Matovic、Zivorad Cekovic、James P. Snyder、Radomir N. Saicic

  DOI：10.1016/j.tetlet.2005.05.071

  日期：2005.7

  A C,D-seco-paclitaxel derivative 12 was prepared and tested for biological activity. The key step in the synthesis was a free radical fragmentation of the bicyclic tertiary alcohol 7 under the conditions of the hypobromite reaction. The compound 12 showed no activity in the tubulin test. (c) 2005 Elsevier Ltd. All rights reserved.