2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene | 168153-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene
• 英文别名: 4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-1-ol
• CAS: 168153-84-2
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: LPZYYIOLDRLZLK-UHFFFAOYSA-N

物化性质

• 沸点：
  511.3±50.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene 在 三氯化铝 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 5,8-dihydroxy-2-(1-hydroxy-4-methylpentyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Shikalkin (±Shikonin) 和相关化合物的合成

  摘要：

  关键中间体2-甲酰基-1,4,5,8-四甲氧基萘是以1,4,5,8-四甲氧基萘为原料，由1,5-萘二醇三步法或萘甲素一步法制得。shikalkin 和二氢shikalkin 的全合成已经用这种醛通过侧链引入与格氏反应和以下去甲基化完成。

  DOI：

  10.1246/bcsj.60.205
• 作为产物：
  描述：

  1,5-二羟基萘 在 sodium hydroxide 、 copper(l) iodide 、 溴 、 三氯氧磷 作用下， 以 甲醇 、 四氯化碳 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene
  参考文献：
  名称：

  shikalkin [（±）-shikonin]的全合成

  摘要：

  首次完成了二氢鹿角蛋白和希卡尔金的全合成。

  DOI：

  10.1039/c39830000987

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。
• Synthesis of Shikalkin (±Shikonin) and Related Compounds
  作者：Akira Terada、Yasuhiro Tanoue、Akira Hatada、Hiroshi Sakamoto

  DOI：10.1246/bcsj.60.205

  日期：1987.1

  2-formyl-1,4,5,8-tetramethoxynaphthalene, was prepared through 1,4,5,8-tetramethoxynaphthalene, which was obtained from 1,5-naphthalenediol via three steps or from naphthazarin via one step. A total synthesis of shikalkin and dihydroshikalkin have been accomplished with this aldehyde via a side-chain introductions with Grignard reactions and the following demethylations.

  关键中间体2-甲酰基-1,4,5,8-四甲氧基萘是以1,4,5,8-四甲氧基萘为原料，由1,5-萘二醇三步法或萘甲素一步法制得。shikalkin 和二氢shikalkin 的全合成已经用这种醛通过侧链引入与格氏反应和以下去甲基化完成。
• Process for preparing 5,8-dihydroxynaphthoquinone derivatives, novel
  申请人：Kuhnil Pharmaceutical Co., Ltd.

  公开号：US05696276A1

  公开（公告）日：1997-12-09

  5,8-dihydroxynaphthoquinone derivatives represented by the following general formula (IA): ##STR1## in which R.sup.1 represents alkyl or alkenyl, R.sup.2a represents alkyl or a group --C(O)R wherein R represents alkyl, alkenyl, aryl, aralkyl or aralkenyl, which can be substituted or unsubstituted with one or more halogen(s), and R.sup.3 represents hydrogen or alkyl, provided that when R.sup.2a is a group --C(O)R and R.sup.3 is hydrogen, R.sup.1 is other than 3-methyl-2-butenyl; and when R.sup.2a represents methyl and R.sup.3 independently represents hydrogen or methyl, R.sup.1 is other than 3-methylbutyl. Processes for preparing 5,8-dihydroxynaphthoquinone derivatives are also provided.

  以如下一般式（IA）代表的5,8-二羟基萘醌衍生物：##STR1## 其中R.sup.1代表烷基或烯基，R.sup.2a代表烷基或一个基团--C(O)R，其中R代表烷基、烯基、芳基、芳基烷基或芳基烯基，可以被一个或多个卤素取代或未取代，R.sup.3代表氢或烷基，条件是当R.sup.2a是一个基团--C(O)R且R.sup.3是氢时，R.sup.1不是3-甲基-2-丁烯基；当R.sup.2a代表甲基且R.sup.3独立地代表氢或甲基时，R.sup.1不是3-甲基丁基。提供了制备5,8-二羟基萘醌衍生物的方法。
• 6-Substituted 1,4-Naphthoquinone Oxime Derivatives (III): Synthesis and Cytotoxic Evaluation
  作者：G. Huang、M. C. Liu、Q. Q. Meng、S. S. Li

  DOI：10.1134/s1070363218050316

  日期：2018.5

  As a continuous study, a set of 23 new 6-substituted 1,4-naphthoquinone oxime derivatives are synthesized and screened for their in vitro cytotoxic activity. Four of those oxime derivatives demonstrate more potent cytotoxic activity towards K562, HCT-15, and HCT-116 cell lines than a reference drug 5-Fu. In particular, compound 21g exhibits the strongest inhibitory activity against K562 cell lines with IC50 values of 1.25 mu M. According to flow cytometry data, compound 21g can arrest cell cycle at S phase and induce a strong apoptotic response in K562 cells. The preliminary structure-activity relationship study shows that the nature of substituents in positions 6 and 1' of 1,4-naphthoquinone derivatives significantly affect their cytotoxic activity.
• TANOUE, YASUHIRO;TERADA, AKIRA, BULL. CHEM. SOC. JAP., 61,(1988) N 6, 2039-2045
  作者：TANOUE, YASUHIRO、TERADA, AKIRA

  DOI：——

  日期：——