Ethyl 2,7,11,15-tetramethyl-2(E),6(E),10(E),14-hexadecatetraenoate | 158897-32-6

• 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: Ethyl 2,7,11,15-tetramethyl-2(E),6(E),10(E),14-hexadecatetraenoate
• 英文别名: ethyl (2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate
• CAS: 158897-32-6
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: HBKXVTWRLRBCQZ-SETKNWSQSA-N

物化性质

• 沸点：
  423.7±34.0 °C(predicted)
• 密度：
  0.901±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal 、 乙氧甲酰基亚乙基三苯基 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到Ethyl 2,7,11,15-tetramethyl-2(E),6(E),10(E),14-hexadecatetraenoate
  参考文献：
  名称：

  Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported. Synthesis of 22 required the stereospecific generation of a vinyl sulfide. This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18). Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33. The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively. Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC50 values of 0.68 and 45 mu M, respectively.

  DOI：

  10.1021/jo00098a048

文献信息

• Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Peter G. Hartman

  DOI：10.1021/jo00098a048

  日期：1994.9

  Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported. Synthesis of 22 required the stereospecific generation of a vinyl sulfide. This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18). Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33. The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively. Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC50 values of 0.68 and 45 mu M, respectively.
• 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.