tert-Butyl-((4R,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane | 872676-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-((4R,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane
• CAS: 872676-77-2
• 化学式: C₂₉H₄₄O₃Si
• 分子量: 468.752
• InChiKey: GKIZMAXROWXFHN-KAYWLYCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-((4R,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
  参考文献：
  名称：

  Total Synthesis as a Resource in Drug Discovery:  The First In Vivo Evaluation of Panaxytriol and Its Derivatives

  摘要：

  We have conducted key preliminary studies into the in vitro and in vivo cytotoxicity of panaxytriol. Through total synthesis, we prepared and evaluated several synthetic panaxytriol analogues, each of which exhibited enhanced cytotoxicity relative to the natural product. Consequently, we have begun to chart the first in vitro SAR map for the compound, which suggests that the C-3 hydroxyl functionality is not critical for biological activity and that, in fact, engagement of the C-9-C-10 diol as an acetonide actually leads to notably enhanced cytotoxicity. Furthermore, through in vivo investigations, we demonstrated that panaxytriol and panaxytriol acetonide (12) moderately suppress tumor growth with little or no toxicity. Finally, preliminary in vitro evaluation of panaxytriol indicates that it possesses neurotrophic activity.

  DOI：

  10.1021/jo0515475
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-Butyl-((4R,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane
  参考文献：
  名称：

  Total Synthesis as a Resource in Drug Discovery:  The First In Vivo Evaluation of Panaxytriol and Its Derivatives

  摘要：

  We have conducted key preliminary studies into the in vitro and in vivo cytotoxicity of panaxytriol. Through total synthesis, we prepared and evaluated several synthetic panaxytriol analogues, each of which exhibited enhanced cytotoxicity relative to the natural product. Consequently, we have begun to chart the first in vitro SAR map for the compound, which suggests that the C-3 hydroxyl functionality is not critical for biological activity and that, in fact, engagement of the C-9-C-10 diol as an acetonide actually leads to notably enhanced cytotoxicity. Furthermore, through in vivo investigations, we demonstrated that panaxytriol and panaxytriol acetonide (12) moderately suppress tumor growth with little or no toxicity. Finally, preliminary in vitro evaluation of panaxytriol indicates that it possesses neurotrophic activity.

  DOI：

  10.1021/jo0515475