2,7,11,15-Tetramethyl-2(E),6(E),10(E),14-hexadecatetraen-1-ol | 158897-33-7

• 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: 2,7,11,15-Tetramethyl-2(E),6(E),10(E),14-hexadecatetraen-1-ol
• 英文别名: (2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol
• CAS: 158897-33-7
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: QAMXLDOWIWCLMD-FNCARBIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,7,11,15-Tetramethyl-2(E),6(E),10(E),14-hexadecatetraen-1-ol 在 三溴化磷 、 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 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：

  Ethyl 2,7,11,15-tetramethyl-2(E),6(E),10(E),14-hexadecatetraenoate 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 生成 2,7,11,15-Tetramethyl-2(E),6(E),10(E),14-hexadecatetraen-1-ol
  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

• Revised structure, synthesis and absolute configuration of hippospongic acid A
  作者：Hideaki Hioki、Masayo Hamano、Yumi Mimura、Mitsuaki Kodama、Shinji Ohta、Mihoko Yanai、Susumu Ikegami

  DOI：10.1016/s0040-4039(98)01688-8

  日期：1998.10

  The structure of hippospongic acid A was reinvestigated and new evidence supporting the revised structure previously proposed was obtained. The structure, including absolute configuration, was established by the enantioselective synthesis.

  对马六甲酸A的结构进行了重新研究，并获得了支持先前提出的修订结构的新证据。通过对映选择性合成建立了包括绝对构型在内的结构。
• Titanium-Mediated Dehydroxylative Cross-Coupling of Allylic Alcohols with Electron-Deficient Olefins
  作者：Liangcai Yao、Jiajing Bao、Yun Wang、Jinghan Gui

  DOI：10.1021/acs.orglett.4c00061

  日期：2024.2.16

  Herein we report a Ti(III)-mediated dehydroxylative cross-coupling reaction of allylic alcohols with electron-deficient olefins. This reaction is amenable to various synthetically versatile allylic alcohols, including geraniol and farnesol, providing a general method for dehydroxylative C–C bond formation. We demonstrated the reaction’s utility by simplifying the syntheses of eight useful building

  在此，我们报道了Ti(III)介导的烯丙醇与缺电子烯烃的脱羟基交叉偶联反应。该反应适用于各种合成多功能烯丙醇，包括香叶醇和金合欢醇，为脱羟基 C-C 键形成提供了通用方法。我们通过简化八种有用的构建模块的合成来证明该反应的实用性，否则这些构建模块的制备起来很费力。
• 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.
• Enantioselective total synthesis and absolute stereostructure of hippospongic acid A
  作者：Hideaki Hioki、Hidenori Ooi、Masayo Hamano、Yumi Mimura、Suzuyo Yoshio、Mitsuaki Kodama、Shinji Ohta、Mihoko Yanai、Susumu Ikegami

  DOI：10.1016/s0040-4020(00)01129-7

  日期：2001.2

  A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.