1,4-dimethoxy-3-(hyroxymethyl)-2-methylnaphthalene | 35993-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dimethoxy-3-(hyroxymethyl)-2-methylnaphthalene
• 英文别名: 1,4-dimethoxy-3-methyl-2-hydroxymethylnaphthalene；2-Methyl-3-oxymethyl-1,4-dimethoxynaphthalin；2-Naphthalenemethanol, 1,4-dimethoxy-3-methyl-；(1,4-dimethoxy-3-methylnaphthalen-2-yl)methanol
• CAS: 35993-25-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: DMWKSKNQUBGQRK-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  405.3±40.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-3-(hyroxymethyl)-2-methylnaphthalene 在 二甲基氧化硒 作用下， 以 苯 为溶剂， 反应 4.5h， 以98%的产率得到1,4-dimethoxy-3-methylnaphthalene-2-carbaldehyde
  参考文献：
  名称：

  A Convenient Oxidation of Halomethylarenes and Alcohols to Aldehydes with Dimethyl Selenoxide and Potassium Benzeneselenite

  摘要：

  DOI：

  10.1055/s-1984-30956
• 作为产物：
  描述：

  1,4-二甲氧基-3-(乙氧羰基)-2-甲基萘 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到1,4-dimethoxy-3-(hyroxymethyl)-2-methylnaphthalene
  参考文献：
  名称：

  Total synthesis of 11-deoxydaunomycinone by a new annulation process

  摘要：

  DOI：

  10.1021/jo00248a014

文献信息

• Phosphoramide compounds
  申请人：——

  公开号：US20030008850A1

  公开（公告）日：2003-01-09

  The invention provides a compound of formula I: 1 wherein R 1 , R a , R b , R c , and R d have any of the values defined in the specification, as well as pharmaceutical compositions comprising such compounds or salts. The compounds are useful for treating cancer in animals.

  本发明提供了一种I式化合物：1，其中R1、Ra、Rb、Rc和Rd的任何值均定义在规范中，以及包含这种化合物或盐的药物组合物。这些化合物对于治疗动物的癌症具有用处。
• Quinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0234729B1

  公开（公告）日：1991-12-27
• Development of Novel Quinone Phosphorodiamidate Prodrugs Targeted to DT-Diaphorase
  作者：Carolee Flader、Jiwen Liu、Richard F. Borch

  DOI：10.1021/jm000179o

  日期：2000.8.1

  A series of naphthoquinone and benzimidazolequinone phosphorodiamidates has been synthesized and studied as potential cytotoxic prodrugs activated by DT-diaphorase. Reduction of the quinone moiety in the target compounds was expected to provide a pathway for expulsion of the phosphoramide mustard alkylating agent. All of the compounds synthesized were excellent substrates for purified human DT-diaphorase (k(cat)/K-m = 3 x 10(7) - 3 x 10(8) M-1 s(-1)). The naphthoquinones were toxic to both HT-29 and BE human colon cancer cell lines in a clonogenic assay; however, cytotoxicity did not correlate with DT-diaphorase activity in these cell lines. The benzimidazolequinone analogues were 1-2 orders of magnitude less cytotoxic than the naphthoquinone analogues. Chemical reduction of the naphthoquinone led to rapid expulsion of the phosphorodiamidate anion; in contrast, the benzimidazole reduction product was stable. Michael addition of glutathione and other sulfur nucleophiles provides an alternate mechanism for activation of the naphthoquinone phosphorodiamidates, and this mechanism may contribute to the cytotoxicity of these compounds.
• TEHRAO, SINDZI;NISIKAVA, KOXEHJ
  作者：TEHRAO, SINDZI、NISIKAVA, KOXEHJ

  DOI：——

  日期：——
• TERAO, SHINJI;NISHIKAWA, KOHEI
  作者：TERAO, SHINJI、NISHIKAWA, KOHEI

  DOI：——

  日期：——