2-苄基-1,4-二甲氧基萘 | 68707-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-苄基-1,4-二甲氧基萘
• 英文名称: 2-benzyl-1,4-dimethoxynaphthalene
• 英文别名: Naphthalene, 1,4-dimethoxy-2-(phenylmethyl)-
• CAS: 68707-65-3
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: BOWCMANKKYEOIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-1,4-二甲氧基萘 在 氢溴酸 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 反应 19.0h， 生成 2-Benzyl-3-(cyanomethyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  The Synthesis of Radermachol

  摘要：

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.

  DOI：

  10.1021/jo00105a046
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 三乙基硅烷 、 四丙基高钌酸铵 、 三氟化硼乙醚 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 2-苄基-1,4-二甲氧基萘
  参考文献：
  名称：

  Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells

  摘要：

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.048

文献信息

• Photoinduced benzylation of 1,4-dimethoxynaphthalene by benzyl halides
  作者：Angelo Albini、Enrico Siviero、Mariella Mella、Conor Long、Albert Pratt

  DOI：10.1039/p29950001895

  日期：——

  Irradiation of 1,4-dimethoxynaphthalene (DMNH) in the presence of 4-substituted benzyl chlorides (X–C6H4CH2Cl, X = H, Cl, CN OR NO2) in either acetonitrile or benezene solution results in benzylation of DMNH, predominantly at position 2 and to a lesser extent on the unsubstitued ring. Steady-state and flash photolysis studies show that charge transfer between singlet excited DMNH and the chlorides

  在4-取代的苄基氯（X–C 6 H 4 CH 2 Cl，X = H，Cl，CN或NO 2）存在下，在乙腈或苯溶液中辐照1,4-二甲氧基萘（DMNH）会导致苄基化DMNH的取代基，主要在2位，未取代的环上程度较小。稳态和快速光解研究表明，涉及单线态激发的DMNH与氯化物之间的电荷转移。该反应主要通过X = H或Cl，而X = NO 2时的协同电子转移和碳-氯键断裂在笼内发生。 苄基氯自由基阴离子的断裂在笼外发生，但在这种情况下，该过程由于竞争性的反向电子传递而效率低得多。
• Synthetic Studies on the Kinamycin Family of Antibiotics:  Synthesis of 2-(Diazobenzyl)-<i>p</i>-naphthoquinone, 1,7-Dideoxy-3-demethylprekinamycin, and 1-Deoxy-3-demethylprekinamycin
  作者：William Williams、Xin Sun、David Jebaratnam

  DOI：10.1021/jo9700484

  日期：1997.6.1

  give 2-(2'-N-acetaminobenzoyl)-1,4-dimethoxynaphthalene, which, following deacylation, was subjected to Pschorr cyclization to give 1,3,7-trihydro-O,O-dimethylkinafluorenone. This was then demethylated, subjected to hydrazinolysis, and then oxidized with Fetizon's reagent to complete the synthesis. 1-Deoxy-3-demethylprekinamycin was synthesized from 3-bromo-1,5-dimethoxy-4-naphthol by an identical route

  由2-苄基-1,4-二甲氧基萘通过硝酸铈铵氧化为2-苄基-对萘醌，然后与甲苯磺酰基叠氮化物进行重氮转移，合成2-（重氮苄基）-对萘醌。由1,4-二甲氧基萘经溴化，锂化和与乙腈缩合制得1,7-二甲氧基-3-脱甲基前激霉素，得到2-（2'-N-乙酰氨基苯甲酰基）-1,4-二甲氧基萘，在脱酰后，将其进行Pschorr环化，得到1,3,7-三氢-O，O-二甲基基芴酮。然后将其脱甲基，进行肼解，然后用Fetizon试剂氧化以完成合成。通过相同的路线，由3-溴-1,5-二甲氧基-4-萘酚合成1-Deoxy-3-demethylprekinamycin。
• The total synthesis of radermachol
  作者：Qingping Jiang、Balawant S. Joshi、S. William Pelletier

  DOI：10.1016/s0040-4039(00)92365-7

  日期：1991.9

  The red pigment, radermachol (1), has been synthesized from 1,4-dimethoxynaphthelene in thirteen steps.
• The Synthesis of Radermachol
  作者：Balawant S. Joshi、Quingping Jiang、Taikyun Rho、S. William Pelletier

  DOI：10.1021/jo00105a046

  日期：1994.12

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.
• Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells
  作者：Suthananda N. Sunassee、Clinton G.L. Veale、Nelusha Shunmoogam-Gounden、Omalaja Osoniyi、Denver T. Hendricks、Mino R. Caira、Jo-Anne de la Mare、Adrienne L. Edkins、Antônio V. Pinto、Eufrânio N. da Silva Júnior、Michael T. Davies-Coleman

  DOI：10.1016/j.ejmech.2012.12.048

  日期：2013.4

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.