1-[3-(furan-3-yl)-3-oxoprop-1-yl]-5-(triisopropylsilyloxy)benzocyclobutene-1-carbonitrile ethylene ketal | 917967-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-(furan-3-yl)-3-oxoprop-1-yl]-5-(triisopropylsilyloxy)benzocyclobutene-1-carbonitrile ethylene ketal
• 英文别名: 7-[2-[2-(Furan-3-yl)-1,3-dioxolan-2-yl]ethyl]-4-tri(propan-2-yl)silyloxybicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile；7-[2-[2-(furan-3-yl)-1,3-dioxolan-2-yl]ethyl]-4-tri(propan-2-yl)silyloxybicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile
• CAS: 917967-37-4
• 化学式: C₂₇H₃₇NO₄Si
• 分子量: 467.681
• InChiKey: XQCQEKWQWPSTRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-(furan-3-yl)-3-oxoprop-1-yl]-5-(triisopropylsilyloxy)benzocyclobutene-1-carbonitrile ethylene ketal 以 邻二氯苯 为溶剂， 反应 2.0h， 以59%的产率得到2,3,5a,10c-tetrahydro-1H,6H-5-oxa-3-oxo-9-(triisopropylsilyloxy)acephenanthrylene-10b-carbonitrile ethylene ketal
  参考文献：
  名称：

  Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic

  摘要：

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.046
• 作为产物：
  描述：

  4-Hydroxy-7-[3-(oxan-2-yloxy)propyl]bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile 在 正丁基锂 、 四丙基高钌酸铵 、 三氟甲磺酸三甲基硅酯 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.92h， 生成 1-[3-(furan-3-yl)-3-oxoprop-1-yl]-5-(triisopropylsilyloxy)benzocyclobutene-1-carbonitrile ethylene ketal
  参考文献：
  名称：

  Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic

  摘要：

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.046

文献信息

• Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic
  作者：Yuji Matsuya、Kazushige Sasaki、Hiroshi Ochiai、Hideo Nemoto

  DOI：10.1016/j.bmc.2006.09.046

  日期：2007.1.1

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.