3-((2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-1H-indole | 871834-08-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-((2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-1H-indole
• 英文别名: 3-[(2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-1H-indole
• CAS: 871834-08-1
• 化学式: C₂₈H₃₉N
• 分子量: 389.624
• InChiKey: CXRJFOQJGMTHSG-ZTNXXJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-((2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-1H-indole 在 squalene:hopene cyclase 、 sodium citrate 、 Triton X-100 作用下， 反应 16.0h， 以5%的产率得到3-[2-[(3R,3aR,5aS,9aS)-3,6,6,9a-tetramethyl-2,3a,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-3-yl]propyl]-1H-indole
  参考文献：
  名称：

  Enzymatic Formation of Indole-Containing Unnatural Cyclic Polyprenoids by Bacterial Squalene:Hopene Cyclase

  摘要：

  [GRAPHICS]Two indole-containing substrate analogues, in which a C-20 isoprene unit is connected to indole (3-(geranylgeranyl)indole and 3-(farnesyldimethylallyl)indole), were synthesized and tested for enzymatic cyclization by squalene:hopene cyclase from Alicyclobacillus acidocaidarius. Interestingly, 3-(geranylgeranyl)indole was not a substrate for the bacterial squalene cyclase, while 3-(farnesyldimethylallyl)indole was efficiently converted to a 2:1 mixture of unnatural novel products.

  DOI：

  10.1021/ol052507q
• 作为产物：
  描述：

  Ethyl 2,7,11,15-tetramethyl-2(E),6(E),10(E),14-hexadecatetraenoate 在 三溴化磷 、 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 生成 3-((2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-1H-indole
  参考文献：
  名称：

  Enzymatic Formation of Indole-Containing Unnatural Cyclic Polyprenoids by Bacterial Squalene:Hopene Cyclase

  摘要：

  [GRAPHICS]Two indole-containing substrate analogues, in which a C-20 isoprene unit is connected to indole (3-(geranylgeranyl)indole and 3-(farnesyldimethylallyl)indole), were synthesized and tested for enzymatic cyclization by squalene:hopene cyclase from Alicyclobacillus acidocaidarius. Interestingly, 3-(geranylgeranyl)indole was not a substrate for the bacterial squalene cyclase, while 3-(farnesyldimethylallyl)indole was efficiently converted to a 2:1 mixture of unnatural novel products.

  DOI：

  10.1021/ol052507q

文献信息

• Enzymatic Formation of Indole-Containing Unnatural Cyclic Polyprenoids by Bacterial Squalene:Hopene Cyclase
  作者：Hideya Tanaka、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1021/ol052507q

  日期：2005.12.1

  [GRAPHICS]Two indole-containing substrate analogues, in which a C-20 isoprene unit is connected to indole (3-(geranylgeranyl)indole and 3-(farnesyldimethylallyl)indole), were synthesized and tested for enzymatic cyclization by squalene:hopene cyclase from Alicyclobacillus acidocaidarius. Interestingly, 3-(geranylgeranyl)indole was not a substrate for the bacterial squalene cyclase, while 3-(farnesyldimethylallyl)indole was efficiently converted to a 2:1 mixture of unnatural novel products.