(3S,5S)-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol | 1172101-91-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3S,5S)-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol
• 英文别名: (3S,5S)-5-[tert-butyl(diphenyl)silyl]oxy-1,7-diphenylhept-1-yn-3-ol
• CAS: 1172101-91-5
• 化学式: C₃₅H₃₈O₂Si
• 分子量: 518.771
• InChiKey: KXRCSJVXGLFKKE-ZWXJPIIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,5S)-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以95%的产率得到(3R,5S)-5-tert-butyldiphenylsilanyloxy-1,7-diphenylheptan-3-ol
  参考文献：
  名称：

  Synthesis of yashabushidiol and its analogues and their cytotoxic activity against cancer cell lines

  摘要：

  A total synthesis of yashabushidiol (1a), a linear diarylheptanoid having 1,3-diol system and its analogues has been achieved by alkynylation of 3-hydroxy-5-phenyl pentanal with substituted phenyl acetylenes. All the compounds have shown significant anti-proliferative activity on human leukemia (THP-1, U-937) and melanoma (A-375) cell lines. Compounds 2a and 2b were found to be most potent with an IC50 of 12.82 mu g/mL and 12.62 mu g/mL, respectively, on THP-1 leukemia cell line. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.061
• 作为产物：
  描述：

  (S)-(3-tert-butyldiphenylsilanyloxy)-5-phenylpentanal 、 苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.25h， 生成 (3S,5S)-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol 、 (3R,5S)-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol
  参考文献：
  名称：

  Synthesis of yashabushidiol and its analogues and their cytotoxic activity against cancer cell lines

  摘要：

  A total synthesis of yashabushidiol (1a), a linear diarylheptanoid having 1,3-diol system and its analogues has been achieved by alkynylation of 3-hydroxy-5-phenyl pentanal with substituted phenyl acetylenes. All the compounds have shown significant anti-proliferative activity on human leukemia (THP-1, U-937) and melanoma (A-375) cell lines. Compounds 2a and 2b were found to be most potent with an IC50 of 12.82 mu g/mL and 12.62 mu g/mL, respectively, on THP-1 leukemia cell line. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.061

文献信息

• Synthesis of yashabushidiol and its analogues and their cytotoxic activity against cancer cell lines
  作者：M. Narasimhulu、T. Srikanth Reddy、K. Chinni Mahesh、A. Sai Krishna、J. Venkateswara Rao、Y. Venkateswarlu

  DOI：10.1016/j.bmcl.2009.03.061

  日期：2009.6

  A total synthesis of yashabushidiol (1a), a linear diarylheptanoid having 1,3-diol system and its analogues has been achieved by alkynylation of 3-hydroxy-5-phenyl pentanal with substituted phenyl acetylenes. All the compounds have shown significant anti-proliferative activity on human leukemia (THP-1, U-937) and melanoma (A-375) cell lines. Compounds 2a and 2b were found to be most potent with an IC50 of 12.82 mu g/mL and 12.62 mu g/mL, respectively, on THP-1 leukemia cell line. (C) 2009 Elsevier Ltd. All rights reserved.