farnesyldimethylallyl bromide | 905305-42-2

• 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: farnesyldimethylallyl bromide
• 英文别名: (2E,6E,10E)-1-bromo-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene
• CAS: 905305-42-2
• 化学式: C₂₀H₃₃Br
• 分子量: 353.386
• InChiKey: OGTPIYMTMOMLJY-FNCARBIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  farnesyldimethylallyl bromide 、 吲哚 在 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 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
• 作为产物：
  描述：

  2,7,11,15-Tetramethyl-2(E),6(E),10(E),14-hexadecatetraen-1-ol 在 三溴化磷 作用下， 以 正己烷 为溶剂， 生成 farnesyldimethylallyl bromide
  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 pyrrole-containing novel cyclic polyprenoids by bacterial squalene:hopene cyclase
  作者：Hideya Tanaka、Hisashi Noma、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1016/j.tetlet.2006.02.151

  日期：2006.5

  A convergent synthesis provided two pyrrole-containing squalene analogues, in which a C(20) isoprene unit is connected to pyrrole, 2-(geranylgeranyl)pyrrole and 2-(farnesyldimethylallyl)pyrrole. When incubated with recombinant squalene:hopene cyclase from Alicyclobacillus acidocaldarius, 2-(farnesyldimethylallyl)pyrrole wits enzymatically converted to a 10: 1 mixture of a tricyclic and a bicyclic unnatural novel polyprenoids, whereas 2-(geranylgeranyl)pyrrole was not a substrate for the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.