1,4-dihydroxy-5,8-dimethoxy-2-naphthonitrile | 197573-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dihydroxy-5,8-dimethoxy-2-naphthonitrile
• 英文别名: 1,4-Dihydroxy-5,8-dimethoxynaphthalene-2-carbonitrile
• CAS: 197573-93-6
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: FMTVITSNZYLWBD-UHFFFAOYSA-N

物化性质

• 沸点：
  515.3±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-dihydroxy-5,8-dimethoxy-2-naphthonitrile 在 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 7.0h， 生成 1,4,5,8-四甲氧基萘-2-甲醛
  参考文献：
  名称：

  A New Efficient Route for Multigram Asymmetric Synthesis of Alkannin and Shikonin

  摘要：

  A short and convergent approach for the synthesis of alkannin, shikonin and shikalkin is presented. A Hauser-type annulation of cyanophthalide 26 with enone 7 affords the complete aromatic system in just one step with concomitant attachment of the entire side chain. Subsequent Corey's oxazaborolidine mediated asymmetric reduction of the above advanced intermediate, leads to the required isomer in high enantiomeric excess. Finally, a selective and high yielding deprotection protocol furnishes the title compounds as pure crystalline precipitates. Thus, a multigram synthesis of shikonin, alkannin and shikalkin is achieved in high yield and enantioselectivity.

  DOI：

  10.1002/1521-3765(20020415)8:8<1795::aid-chem1795>3.0.co;2-v
• 作为产物：
  描述：

  1(3H)-Isobenzofuranone, 4,7-dimethoxy-3-(phenylsulfonyl)- 、 丙烯腈 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1,4-dihydroxy-5,8-dimethoxy-2-naphthonitrile
  参考文献：
  名称：

  Asymmetric synthesis of alkannin and shikonin

  摘要：

  A new general and convergent route for the synthesis of the title compounds is presented. The polyoxygenated aromatic ring system is annulated in one operation by the condensation of a Michael type acceptor with an 1,4 dipole equivalent. The chiral center of the target is introduced via an asymmetric allyl boration in high ee. Overall, the fully protected natural product is constructed within 8 steps in 35% total yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01687-0

文献信息

• Electroreductive Coupling of Phthalic Anhydrides with α,β-Unsaturated Carbonyl Compounds: Synthesis of 1,4-Dihydroxynaphthalenes
  作者：Naoki Kise、Shota Yamamoto、Toshihiko Sakurai

  DOI：10.1021/acs.joc.0c02000

  日期：2020.11.6

  Electroreductive coupling of phthalic anhydrides with α,β-unsaturated carbonyl compounds in the presence of TMSCl and subsequent treatment with 1 M HCl gave 1,4-dihydroxynaphthalenes and 2-methyl-2,3-dihydronaphthalene-1,4-diones.

  在TMCSI存在下，邻苯二甲酸酐与α，β-不饱和羰基化合物的电还原偶联，随后用1M HCl处理，得到1，4-二羟基萘和2-甲基-2，3-二氢萘-1，4-二酮。