(1,4,5,8-tetramethoxy-2-naphthyl)methanol | 97476-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1,4,5,8-tetramethoxy-2-naphthyl)methanol
• 英文别名: 2-hydroxymethyl-1,4,5,8-tetramethoxynaphthalene；(1,4,5,8-tetramethoxynaphthalen-2-yl)methanol
• CAS: 97476-18-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: DDJJXZMFKAMQBB-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C(Solv: hexane (110-54-3); benzene (71-43-2))
• 沸点：
  466.8±40.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1,4,5,8-tetramethoxy-2-naphthyl)methanol 在 正丁基锂 、 1,1,2,2-四氟-1,2-二溴乙烷 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 Methanesulfonic acid 3-bromo-1,4,5,8-tetramethoxy-naphthalen-2-ylmethyl ester
  参考文献：
  名称：

  Absolute stereochemistry of 1,2′-linked bi(naphthoquinone)s

  摘要：

  天然存在的1,2-联萘醌和对映异构体8-羟基异二氧呋喃和对二氧呋喃的非对称合成，使得它们的绝对构型可以通过合成中间体的X射线和圆二色光谱研究来确定。

  DOI：

  10.1039/a607720j
• 作为产物：
  描述：

  1,5-二羟基萘 在 N-溴代丁二酰亚胺(NBS) 、 hydrazine hydrate 、 sodium hydroxide 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (1,4,5,8-tetramethoxy-2-naphthyl)methanol
  参考文献：
  名称：

  An efficient reduction of nitro and bromine naphthalene derivatives

  摘要：

  Reduction of 1,5-dimethoxy-4-nitronaphthalene by hydrazine hydrate was optimized in the course of current study. Influence of metals, temperature and solvents upon the process was tested. Yield of the reaction was the highest in the presence of Zn powder in DMF. Moderate heating made the process slightly more efficient than that at room temperature, whereas high temperature led to a decreased yield. The current approach made it possible to exclude high pressure and diminish experimental costs.

  DOI：

  10.1134/s1070363217040272

文献信息

• The 2- or 6-(α-Hydroxyalkyl- and α-Oxoalkyl)-5,8-dimethoxy-1,4-naphthoquinones from the Oxidative Demethylation of 2-(α-Hydroxyalkyl- and α-Oxoalkyl)-1,4,5,8-tetramethoxynaphthalenes with Cerium(IV) Ammonium Nitrate, and the Further Demethylations to Naphthazarins
  作者：Yasuhiro Tanoue、Akira Terada

  DOI：10.1246/bcsj.61.2039

  日期：1988.6

  Oxidative demethylation of 2-(α-hydroxyalkyl- and α-oxoalkyl)-1,4,5,8-tetramethoxynaphthalene with (NH4)2Ce(NO3)6 gave two isomeric dimethoxynaphthoquinones: 2-substituted and 6-substituted 5,8-dimethoxy-1,4-naphthoquinones. Further demethylations of the former isomers to the corresponding dihydroxynaphthoquinones required an AgO–40%HNO3 reagent, while the latter isomers needed AlCl3 as the demethylation

  2-(α-羟烷基-和α-氧代烷基)-1,4,5,8-四甲氧基萘与 (NH4)2Ce(NO3)6 的氧化脱甲基得到两种异构二甲氧基萘醌：2-取代和 6-取代的 5,8-二甲氧基-1,4-萘醌。前者异构体进一步去甲基化为相应的二羟基萘醌需要 AgO–40%HNO3 试剂，而后者异构体需要 AlCl3 作为去甲基化试剂。给出了关于这些用 (NH4)2Ce(NO3)6 进行氧化去甲基化的机制的一些评论。
• Regioselectivity in the Lithiation of 1,3-Disubstituted Arenes
  作者：Robert W. Baker、Song Liu、Melvyn V. Sargent、Brian W. Skelton、Allan H. White

  DOI：10.1071/c97016

  日期：——

  The regioselectivity of the lithiation of 1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde (7) with butyllithium or phenyllithium in the presence of N,N,N′-trimethylethylenediamine and the subsequent bromination of the lithiated species so generated with 1,2-dibromotetrafluoroethane were investigated. Similar investigations with butyllithium as base in the presence of N,N,N′,N′-tetramethylethylenediamine or potassium t-butoxide were carried out on 1,4,5,8-tetramethoxynaphthalene-2-methanol (14). These studies were extended to 1,5,8-trimethoxynaphthalene-3-methanol (25), 3-methoxybenzenemethanol (29) and 3,5-dimethoxybenzenemethanol (32). The X-ray crystal structure of 6-bromo-1,4,5,8-tetramethoxynaphthalene-2-methanol (17) is described.

  1,4,5,8-四甲氧基萘-2-甲醛（7）与丁基锂或 1,4,5,8-四甲氧基萘-2-甲醛 (7) 与丁基锂或 的存在下，1,4,5,8-四甲氧基萘-2-甲醛（7）与丁锂或 N,N,N′-三甲基乙二胺 并将生成的锂化物与 1,2-二溴四氟乙烷进行溴化。以 以丁基锂为碱，在 N,N,N′,N′-四甲基乙二胺 或叔丁醇钾对 1,4,5,8-四甲氧基萘-2-甲醇 (14)。这些研究 1,5,8-三甲氧基萘-3-甲醇 (25)、3-甲氧基苯甲醇 (29) 和 3,5-二甲氧基苯甲醇 (32)。的 X 射线晶体结构。 描述了 6-溴-1,4,5,8-四甲氧基萘-2-甲醇（17）的 X 射线晶体结构。
• Monosubstituted Tetramethoxynaphthalenes
  作者：Yasuhiro Tanoue、Akira Terada、Kazuhiko Torisu、Hiroshige Taniguchi

  DOI：10.1246/bcsj.62.1211

  日期：1989.4.15

  As new intermediates for the syntheses of monosubstituted naphthazarins and anthracyclines, several tetramethoxynaphthalenes having a substituent such as CH3, COOH, CN, Br, OAc, OH, and OMe groups were prepared from 1,4,5,8-tetramethoxynaphthalene and 2-formyl-1,4,5,8-tetramethoxynaphthalene.

  作为合成单取代萘扎林和蒽环类化合物的新中间体，几种具有 CH3、COOH、CN、Br、OAc、OH 和 OMe 等取代基的四甲氧基萘被从 1,4,5,8-四甲氧基萘和 2-甲酰基-1,4,5,8-四甲氧基萘合成出来。
• [EN] PROTEIN KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINE KINASE
  申请人：XAVIER UNIV OF LOUISIANA

  公开号：WO2020076905A1

  公开（公告）日：2020-04-16

  The present disclosure relates to compounds that act as protein kinase inhibitors, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for proliferative diseases, including cancer, particularly breast cancer, and especially ER+ and/or HER2+ breast cancer.

  本公开涉及作为蛋白激酶抑制剂的化合物，以及其合成。此外，本公开教导了利用这些化合物治疗增殖性疾病，包括癌症，特别是乳腺癌，尤其是ER+和/或HER2+乳腺癌。
• Convenient Synthesis of 1,4-Naphthoquinones from Polymethoxynaphthalenes. Oxidative Demethylation with Silver-Catalyzed Ammonium Peroxodisulfate
  作者：Yasuhiro Tanoue、Kazunori Sakata、Mamoru Hashimoto、Shin-ichi Morishita、Moritsugu Hamada、Norihisa Kai、Takeshi Nagai

  DOI：10.1246/bcsj.67.2593

  日期：1994.9

  The oxidative demethylation of polymethoxynaphthalenes such as 1,4-di, 1,4,5-tri, 1,4,5,8-tetra, and 1,2,4,5,8-pentamethoxynaphthalenes with silver-catalyzed ammonium peroxodisulfate gave the corresponding 1,4-naphthoquinones in good yield under mild reaction conditions.

  在银催化的过二硫酸铵作用下，1,4-二、1,4,5-三、1,4,5,8-四和 1,2,4,5,8-五甲氧基萘等多甲氧基萘在温和的反应条件下发生氧化脱甲基反应，得到了相应的 1,4-萘醌，收率很高。