2,3,4-trimethoxybenzyl(triphenyl)phosphonium chloride | 139214-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-trimethoxybenzyl(triphenyl)phosphonium chloride
• 英文别名: Triphenyl-[(2,3,4-trimethoxyphenyl)methyl]phosphanium;chloride
• CAS: 139214-82-7
• 化学式: C₂₈H₂₈O₃P*Cl
• 分子量: 478.955
• InChiKey: ZQUFZDLSINHZCM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxybenzyl(triphenyl)phosphonium chloride 在 palladium on activated charcoal 甲基碘化镁 、 lithium methanolate 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.5h， 生成 3,3'-dihydroxy-2,2',4,4'-tetramethoxybibenzyl
  参考文献：
  名称：

  On the synthesis of a phenanthrene-2,7-quinone

  摘要：

  Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51% yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type. Similar oxidation of the corresponding diphenylethane 55 gave the 9,10-dihydrophenanthrene-2,7-quinone 56. Attempts to synthesize the tetramethoxyphenanthrene-2,7-diol 25 from a 2,2'-bis(hydroxymethyl)hexamethoxybiphenyl precursor 28 were thwarted by the ease of intramolecular cyclization to 2,3,4,8,9,10-hexamethoxydibenz[c,e]oxepine 32. Selective demethylation of the 3- and 9-methoxy groups of this compound, and oxidation of the resulting diol 58 gave the dibenzoxepine quinone 59.The synthesis of 3,6-di-tert-butylphenanthrene-2,7-diol 3 is also described, but this could not be oxidized to the quinone. However, the preparation of 3,6-di-tert-butyl-9,10-dihydrophenanthrene-2,7-quinone 12 was successful.

  DOI：

  10.1039/p19910003033
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醇 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 45.5h， 生成 2,3,4-trimethoxybenzyl(triphenyl)phosphonium chloride
  参考文献：
  名称：

  On the synthesis of a phenanthrene-2,7-quinone

  摘要：

  Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51% yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type. Similar oxidation of the corresponding diphenylethane 55 gave the 9,10-dihydrophenanthrene-2,7-quinone 56. Attempts to synthesize the tetramethoxyphenanthrene-2,7-diol 25 from a 2,2'-bis(hydroxymethyl)hexamethoxybiphenyl precursor 28 were thwarted by the ease of intramolecular cyclization to 2,3,4,8,9,10-hexamethoxydibenz[c,e]oxepine 32. Selective demethylation of the 3- and 9-methoxy groups of this compound, and oxidation of the resulting diol 58 gave the dibenzoxepine quinone 59.The synthesis of 3,6-di-tert-butylphenanthrene-2,7-diol 3 is also described, but this could not be oxidized to the quinone. However, the preparation of 3,6-di-tert-butyl-9,10-dihydrophenanthrene-2,7-quinone 12 was successful.

  DOI：

  10.1039/p19910003033

文献信息

• CYP1-Activation and Anticancer Properties of Synthetic Methoxylated Resveratrol Analogues
  作者：Ketan C. Ruparelia、Keti Zeka、Kenneth J. M. Beresford、Nicola E. Wilsher、Gerry A. Potter、Vasilis P. Androutsopoulos、Federico Brucoli、Randolph R. J. Arroo

  DOI：10.3390/molecules29020423

  日期：——

  (Z)-stilbenoid combretastatin A4, have been considered as promising lead compounds for the development of anticancer drugs. The antitumour properties of stilbenoids are known to be modulated by cytochrome P450 enzymes CYP1A1 and CYP1B1, which contribute to extrahepatic phase I xenobiotic and drug metabolism. Thirty-four methyl ether analogues of resveratrol were synthesised, and their anticancer properties were

  天然存在的二苯乙烯类化合物，如 （E）-二苯乙烯类白藜芦醇和 （Z）-二苯乙烯类化合物 combretastatin A4，已被认为是开发抗癌药物的有前途的先导化合物。已知二苯乙烯类化合物的抗肿瘤特性受细胞色素 P450 酶 CYP1A1 和 CYP1B1 的调节，这有助于肝外 I 期外源性物质和药物代谢。合成白藜芦醇的 34 种甲基醚类似物，并在一组人乳腺细胞系上使用 MTT 细胞增殖测定评估其抗癌特性。表达 CYP1 的乳腺肿瘤细胞系比不具有 CYP1 活性的细胞系受白藜芦醇类似物的影响明显更强。使用分离的 CYP1 酶的代谢研究提供了进一步的证据，证明 （E）-二苯乙烯类化合物可以成为这些酶的底物。通过与合成标准品和 LC-MS 共洗脱研究进行比较来确认代谢产物的结构。最有前途的二苯乙烯类化合物是 （E）-4,3′，4′，5′-四甲氧基二苯乙烯 （DMU212）。该化合物本身显示出低至中度的细胞毒性，但在