(2E,6E,10E)-3,7,11-trimethyl-14-oxotetradeca-2,6,10-trien-1-yl acetate | 142673-23-2

• 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: (2E,6E,10E)-3,7,11-trimethyl-14-oxotetradeca-2,6,10-trien-1-yl acetate
• 英文别名: 13-Formyl-3,7,11-trimethyltrideca-2(E),6(E),10(E)-trienyl ethanoate；(4E,8E,12E)-14-Acetoxy-4,8,12-trimethyltetradeca-2,6,10-trienal；(E,E,E)-14-acetoxy-4,8,12-trimethyl-4,8,12-tetradecatrienal；[(2E,6E,10E)-3,7,11-trimethyl-14-oxotetradeca-2,6,10-trienyl] acetate
• CAS: 142673-23-2
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: OGEPAMCEQAELHM-ZJOIEPKXSA-N

物化性质

• 沸点：
  413.6±45.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,6E,10E)-3,7,11-trimethyl-14-oxotetradeca-2,6,10-trien-1-yl acetate 在 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (E,E,E)-14-(dimethylamino)-3,7,11-trimethyl-2,6,10-hexadecatrienol
  参考文献：
  名称：

  SN2置换磷酸二乙酯合成烯丙基异戊二烯二磷酸酯

  摘要：

  烯丙基多烯基二磷酸酯如香叶基和 (E,E,E)-香叶基香叶基二磷酸酯是类异戊二烯生物合成中单萜和二萜合酶和转移酶普遍存在的底物。这些酶底物是通过用 (R)-和 (S)-Alpine boranes® 还原 1-氘醛前体，转化为磷酸二乙酯，以及用焦磷酸三（四丁基铵）缓慢发生的 SN2 置换，以不对称标记的形式制备的在 2-5 天内完成配置反转。用去甲二醇 11、(15S)-[15-] 类似地制备了 8α-和 8β-羟基-17-nor 类似物（13 和 14）以及 13 的（15R）-氘标记形式2H1]-11 和 12 通过烯丙基羟基的区域选择性磷酸化和焦磷酸阴离子置换。SN2 置换前后氘标记香叶醇的构型和对映纯度，以及双环酮醇中间体 (15S)-[15-2H1]-15 的非对映纯度通过转化为 (1S)-莰酸酯和1H-NMR分析。氨基醇 18 类似地转化为氨基二磷酸 19, 15-aza-14

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1401::aid-ejoc1401>3.0.co;2-p
• 作为产物：
  描述：

  香叶基香叶醇 在 N-溴代丁二酰亚胺(NBS) 、 过碘酸 作用下， 以 吡啶 、 水 为溶剂， 生成 (2E,6E,10E)-3,7,11-trimethyl-14-oxotetradeca-2,6,10-trien-1-yl acetate
  参考文献：
  名称：

  Synthesis of Plaunotol Derivatives and their Antibacterial Activities against Helicobacter pylori

  摘要：

  Plaunotol, a known antiulcer drug, has antibacterial activities against Helicobacter pylori. Plaunotol thiourea derivatives 2-4 and diol derivatives 6-10 were designed in search For a compound with high amtobacteroa; activities. Thiourea derivatives 2-4 were synthesized regioselectively using our effective synthetic route for plaunotol (1), and diol derivatives 6 10 were also synthesized. Their antibacterial activities against H. pylori are described and we found that the most potent antibacterial agent was Cl-thiourea derivative 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00080-3

文献信息

• Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for<i>in vivo</i>mass spectrometric quantification
  作者：Thangaiah Subramanian、Karunai Leela Subramanian、Manjula Sunkara、Fredrick O. Onono、Andrew J. Morris、H. Peter Spielmann

  DOI：10.1002/jlcr.3049

  日期：2013.6.30

  A Wittig reaction employing Li(CD3)2CP(C6H5)3 was used to prepare d6-farnesol and d6-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d5 was used to prepare the unnatural isoprenoid analogues d5-anilinogeraniol and d5-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis.

  使用 Li(CD3)2CP(C6H5)3 的 Wittig 反应合成了 d6-法尼醇和 d6-戊烯醇。利用 2,3,4,5,6-d5-苯胺的还原胺化反应合成了不自然的异戊烯类类似物 d5-苯胺戊烯醇和 d5-苯胺法尼醇。所有这些重氢化异戊醇均被转化为其二磷酸盐和半胱氨酸硫醚衍生物，这些衍生物适合用作定量质谱分析的稳定同位素标记标准。
• Synthesis of lurlene, the sex pheromone of the green flagellate Chlamydomonas allensworthii
  作者：Kenji Mori、Shin-ichi Takanashi

  DOI：10.1016/0040-4039(96)00127-x

  日期：1996.3

  Lurlene [(4E,8E,12E)-14-[2'-hydroxy-3',4'-dimethyl-5'-(1 ''-beta-D-xylopyranosyloxy)phenyl]-4,8,12-trimethyltetradeca-4,8,12-trienoic acid, 1], the sex pheromone produced by the female gametes of Chlamydomonas allensworthii, was synthesized as a mixture of 1 and its (12Z)-isomer, and the mixture was bioactive.
• Cox, Nicolas J. G.; Mills, Stuart D.; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1992, # 11, p. 1313 - 1322
  作者：Cox, Nicolas J. G.、Mills, Stuart D.、Pattenden, Gerald

  DOI：——

  日期：——
• Synthesis of Allylic Isoprenoid Diphosphates by SN2 Displacement of Diethyl Phosphate
  作者：Matthew M. Ravn、Qingwu Jin、Robert M. Coates

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1401::aid-ejoc1401>3.0.co;2-p

  日期：2000.4

  Allylic polyenyl diphosphates such as geranyl and (E,E,E)-geranylgeranyl diphosphates are ubiquitous substrates for monoterpene and diterpene synthases and transferases in isoprenoid biosynthesis. These enzyme substrates were prepared in asymmetrically labeled form by reduction of 1-deuterio aldehyde precursors with (R)- and (S)-Alpine boranes®, conversion into diethyl phosphates, and SN2 displacements

  烯丙基多烯基二磷酸酯如香叶基和 (E,E,E)-香叶基香叶基二磷酸酯是类异戊二烯生物合成中单萜和二萜合酶和转移酶普遍存在的底物。这些酶底物是通过用 (R)-和 (S)-Alpine boranes® 还原 1-氘醛前体，转化为磷酸二乙酯，以及用焦磷酸三（四丁基铵）缓慢发生的 SN2 置换，以不对称标记的形式制备的在 2-5 天内完成配置反转。用去甲二醇 11、(15S)-[15-] 类似地制备了 8α-和 8β-羟基-17-nor 类似物（13 和 14）以及 13 的（15R）-氘标记形式2H1]-11 和 12 通过烯丙基羟基的区域选择性磷酸化和焦磷酸阴离子置换。SN2 置换前后氘标记香叶醇的构型和对映纯度，以及双环酮醇中间体 (15S)-[15-2H1]-15 的非对映纯度通过转化为 (1S)-莰酸酯和1H-NMR分析。氨基醇 18 类似地转化为氨基二磷酸 19, 15-aza-14
• Synthesis of Plaunotol Derivatives and their Antibacterial Activities against Helicobacter pylori
  作者：Keiko Tago、Emiko Minami、Kayoko Masuda、Toshiyuki Akiyama、Hiroshi Kogen

  DOI：10.1016/s0968-0896(01)00080-3

  日期：2001.7

  Plaunotol, a known antiulcer drug, has antibacterial activities against Helicobacter pylori. Plaunotol thiourea derivatives 2-4 and diol derivatives 6-10 were designed in search For a compound with high amtobacteroa; activities. Thiourea derivatives 2-4 were synthesized regioselectively using our effective synthetic route for plaunotol (1), and diol derivatives 6 10 were also synthesized. Their antibacterial activities against H. pylori are described and we found that the most potent antibacterial agent was Cl-thiourea derivative 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.