3-((2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-pyrrole | 887403-62-5

• 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)-pyrrole
• 英文别名: 2-(farnesyldimethylallyl)pyrrole；2-[(2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-1H-pyrrole
• CAS: 887403-62-5
• 化学式: C₂₄H₃₇N
• 分子量: 339.564
• InChiKey: WABYJMOGOZFDJM-HZOREIBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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)-pyrrole 在 Alicyclobacillus acidocaldarius SHC 、 sodium citrate 、 Triton X-100 作用下， 以 水 为溶剂， 反应 16.0h， 以0.2 mg的产率得到2-[2-((3R,3aS,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyl-dodecahydro-cyclopenta[a]naphthalen-3-yl)-allyl]-1H-pyrrole
  参考文献：
  名称：

  Enzymatic formation of pyrrole-containing novel cyclic polyprenoids by bacterial squalene:hopene cyclase

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.02.151
• 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)-pyrrole
  参考文献：
  名称：

  Enzymatic formation of pyrrole-containing novel cyclic polyprenoids by bacterial squalene:hopene cyclase

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.02.151

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.