1,2,3,4-tetramethoxy-5-methyl-6-<(2E)-farnesyl>benzene | 95778-33-9

• 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: 1,2,3,4-tetramethoxy-5-methyl-6-<(2E)-farnesyl>benzene
• 英文别名: (2'E,6'E)-1-(3,7,11-trimethyldodeca-2,6,10-trienyl)-6-methyl-2,3,4,5-tetramethoxybenzene；1,2,3,4-tetramethoxy-5-methyl-6-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)benzene；1,2,3,4-Tetramethoxy-5-methyl-6-(3,7,11-trimethyl-2,6,10-dodecatrienyl)benzene；1,2,3,4-tetramethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene
• CAS: 95778-33-9
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: XUKZWFXRDDPNAW-XHGFWWIISA-N

物化性质

• 沸点：
  515.7±50.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetramethoxy-5-methyl-6-<(2E)-farnesyl>benzene 在 吡啶-2,6-二甲酸 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以84%的产率得到2,5-环己二烯-1,4-二酮,2,3-二甲氧基-5-甲基-6-[(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-基]-
  参考文献：
  名称：

  Total synthesis of linear polyprenoids. 2. Improved preparation of the aromatic nucleus of ubiquinone

  摘要：

  DOI：

  10.1021/jo00226a028
• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 盐酸 、 bis(triphenylphosphine)nickel(II) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 生成 1,2,3,4-tetramethoxy-5-methyl-6-<(2E)-farnesyl>benzene
  参考文献：
  名称：

  A Convergent Approach to Coenzyme Q

  摘要：

  Syntheses of coenzyme Q(3-8) are described, as well as related systems such as plastoquinone-5. Preparation of thr higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.

  DOI：

  10.1021/ja992164p

文献信息

• Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities
  作者：Hitoshi Kamauchi、Takumi Oda、Kanayo Horiuchi、Koichi Takao、Yoshiaki Sugita

  DOI：10.1016/j.bmc.2019.115156

  日期：2020.1

  natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values < 25 μM) and the inhibition mode and molecular docking of two (8c and 16c) were investigated. Compounds inhibiting MAO-B activity were additionally tested for their ability to protect

  合成了27种天然产物状的聚异戊二烯基酚和醌，并使用人单胺氧化酶B（MAO-B）和SH-SY5Y细胞测试了它们的神经保护活性。八种化合物抑制了MAO-B（IC50值<25μM），并研究了两种化合物（8c和16c）的抑制模式和分子对接。还测试了抑制MAO-B活性的化合物保护SH-SY5Y细胞免于过氧化物损伤的能力。三种衍生物（3c，8c和16c）同时具有MAO-B抑制和神经保护作用。结构活性关系研究表明，酚羟基和较长的侧链对于这两种活性都很重要。
• Convenient Syntheses of Vitamin K and Coenzyme Q by the Coupling of Grignard Reagents with Allylic Phosphate
  作者：Shuki Araki、Takashi Sato、Hiroyuki Miyagawa、Yasuo Butsugan

  DOI：10.1246/bcsj.57.3523

  日期：1984.12

  described. Grignard coupling of polyprenyl diethyl phosphates with 1,4-dimethoxy-3-methyl-2-naphthylmagnesium bromide gave high yields of the polyprenylated hydroquinone dimethyl ethers regioselectively with the preservation of the stereochemistry. The precursors of coenzyme Q were similarly obtained by the coupling of 2,3,4,5-tetramethoxy-6-methylphenylmagnesium bromide and the polyprenyl phosphates. The

  描述了维生素 K 和辅酶 Q 的方便合成。聚异戊二烯二乙基磷酸酯与 1,4-二甲氧基-3-甲基-2-萘基溴化镁的格氏偶联在保留立体化学的情况下区域选择性地得到高产率的聚异戊二烯化氢醌二甲醚。辅酶 Q 的前体类似地通过 2,3,4,5-四甲氧基-6-甲基苯基溴化镁和聚异戊二烯基磷酸酯的偶联获得。已知合成的（聚异戊二烯基）氢醌二甲醚被氧化为具有生物活性的醌。
• Synthesis of 1,2,3,4-Tetrahydroxybenzene from <scp>d</scp>-Glucose:  Exploiting <i>myo</i>-Inositol as a Precursor to Aromatic Chemicals
  作者：Chad A. Hansen、Amy B. Dean、K. M. Draths、J. W. Frost

  DOI：10.1021/ja9840293

  日期：1999.4.1
• KEINAN, EHUD;EREN, DORON, J. ORG. CHEM., 52,(1987) N 17, 3872-3875
  作者：KEINAN, EHUD、EREN, DORON

  DOI：——

  日期：——
• A Convergent Approach to Coenzyme Q
  作者：Bruce H. Lipshutz、Gerd Bulow、Fernando Fernandez-Lazaro、Sung-Kyu Kim、Richard Lowe、Paul Mollard、Kirk L. Stevens

  DOI：10.1021/ja992164p

  日期：1999.12.1

  Syntheses of coenzyme Q(3-8) are described, as well as related systems such as plastoquinone-5. Preparation of thr higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.