(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-6-(2-cyanoethyl)-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate | 204764-83-0

• 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: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-6-(2-cyanoethyl)-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
• CAS: 204764-83-0
• 化学式: C₃₈H₅₃NO₉Si
• 分子量: 695.926
• InChiKey: LTWBKUHRAGUNEY-NLDOSCHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  152.38
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-6-(2-cyanoethyl)-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 在 镍 4-二甲氨基吡啶 、 ammonium hydroxide 、 甲酸 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-12-(3-aminopropyl)-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs

  摘要：

  An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00040-7
• 作为产物：
  描述：

  丙烯腈 、 10-deacetyl-10-(S-methylxanthyl)-7-(triethylsilyl)baccatin III 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以58%的产率得到(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-6-(2-cyanoethyl)-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs

  摘要：

  An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00040-7