3-Vinyl-benzoic acid (2S,8S,8aR)-5-oxo-2-triisopropylsilanyloxy-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester | 728896-05-7

• 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: 3-Vinyl-benzoic acid (2S,8S,8aR)-5-oxo-2-triisopropylsilanyloxy-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester
• CAS: 728896-05-7
• 化学式: C₂₆H₃₇NO₄Si
• 分子量: 455.67
• InChiKey: SWOONKLKDCRNRP-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Vinyl-benzoic acid (2S,8S,8aR)-5-oxo-2-triisopropylsilanyloxy-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester 在 4-吡咯烷基吡啶 、 氟化氢吡啶 、 达卡巴嗪 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 41.0h， 生成 3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester
  参考文献：
  名称：

  Design and synthesis of de novo cytotoxic alkaloids through mimicking taxoid skeleton

  摘要：

  Based on a common pharmacophore model and the hypothesis that the baccatin core of taxoids is a scaffold securing the proper orientation of the side chains, a bicyclic alkaloid scaffold was designed as a baccatin surrogate. Using this scaffold, two novel macrocyclic and open-chain 'taxoid-mimicking' compounds were synthesized. Two of these 'taxoid-mimics', 2 and 3, were found to possess cytotoxicity with micromolar level IC50 values against human breast cancer cell lines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.060
• 作为产物：
  描述：

  (2R,4S)-4-Triisopropylsilanyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 锂硼氢 、 pyridine-SO3 complex 、 potassium carbonate 、 二甲基亚砜 、 达卡巴嗪 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 3-Vinyl-benzoic acid (2S,8S,8aR)-5-oxo-2-triisopropylsilanyloxy-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester
  参考文献：
  名称：

  Design and synthesis of de novo cytotoxic alkaloids through mimicking taxoid skeleton

  摘要：

  Based on a common pharmacophore model and the hypothesis that the baccatin core of taxoids is a scaffold securing the proper orientation of the side chains, a bicyclic alkaloid scaffold was designed as a baccatin surrogate. Using this scaffold, two novel macrocyclic and open-chain 'taxoid-mimicking' compounds were synthesized. Two of these 'taxoid-mimics', 2 and 3, were found to possess cytotoxicity with micromolar level IC50 values against human breast cancer cell lines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.060