methyl (3-allyl-1,4-dimethoxynaphthalene-2-yl)carboxylate | 221122-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (3-allyl-1,4-dimethoxynaphthalene-2-yl)carboxylate
• 英文别名: Methyl 1,4-dimethoxy-3-prop-2-enylnaphthalene-2-carboxylate
• CAS: 221122-91-4
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: RHTPETIBRKJMEG-UHFFFAOYSA-N

物化性质

• 沸点：
  438.5±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3-allyl-1,4-dimethoxynaphthalene-2-yl)carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以96%的产率得到2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Total Synthesis of Two Naphthoquinone Antibiotics, Psychorubrin and Pentalongin, and Their C(1)-Substituted Alkyl and Aryl Derivatives

  摘要：

  The synthesis of 1-alkyl- and 1-aryl-1H-naphtho[2,3-c]pyran-5,10-dione bearing a C(3)-C(4) double bond, was performed by two alternative cyclization strategies of 2,3-disubstituted 1,4-naphthoquinones. Lemieux-Johnson oxidation of 2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalenes and subsequent oxidative demethylation of the intermediate 3,4-dihydro-5,10-dimethoxy-1H-naphtho[2,3 -c]pyran-3-oles to the corresponding 3,4-dihydro-3-hydroxy-1H-naphtho[2,3-c]pyran-5, 10-diones gave, after acid-catalyzed dehydration, the de shed 1H-naphtho[2,3-c]pyran-5,10-diones. Alternatively, the pyranonaphthoquinone ring system was constructed by intramolecular acid-catalyzed condensation of(3-hydroxymethyl-1,4-naphthoquinone-2-yl)acetaldehyde acetals. Using this synthetic approach, the synthesis of two naturally occurring naphthoquinone antibiotics, pentalongin and psychorubrin, is reported.

  DOI：

  10.1021/jo9811975
• 作为产物：
  描述：

  2-allyl-3-bromo-1,4-naphthoquinone 在 盐酸 、 氢氧化钾 、 正丁基锂 、 tin(ll) chloride 作用下， 反应 3.5h， 生成 methyl (3-allyl-1,4-dimethoxynaphthalene-2-yl)carboxylate
  参考文献：
  名称：

  Total Synthesis of Two Naphthoquinone Antibiotics, Psychorubrin and Pentalongin, and Their C(1)-Substituted Alkyl and Aryl Derivatives

  摘要：

  The synthesis of 1-alkyl- and 1-aryl-1H-naphtho[2,3-c]pyran-5,10-dione bearing a C(3)-C(4) double bond, was performed by two alternative cyclization strategies of 2,3-disubstituted 1,4-naphthoquinones. Lemieux-Johnson oxidation of 2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalenes and subsequent oxidative demethylation of the intermediate 3,4-dihydro-5,10-dimethoxy-1H-naphtho[2,3 -c]pyran-3-oles to the corresponding 3,4-dihydro-3-hydroxy-1H-naphtho[2,3-c]pyran-5, 10-diones gave, after acid-catalyzed dehydration, the de shed 1H-naphtho[2,3-c]pyran-5,10-diones. Alternatively, the pyranonaphthoquinone ring system was constructed by intramolecular acid-catalyzed condensation of(3-hydroxymethyl-1,4-naphthoquinone-2-yl)acetaldehyde acetals. Using this synthetic approach, the synthesis of two naturally occurring naphthoquinone antibiotics, pentalongin and psychorubrin, is reported.

  DOI：

  10.1021/jo9811975

文献信息

• Pericyclic Reactions of Prenylated Naphthoquinones:  Biomimetic Syntheses of Mollugin and Microphyllaquinone
  作者：Jean-Philip Lumb、Dirk Trauner

  DOI：10.1021/ol052472u

  日期：2005.12.1

  [GRAPHICS]A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6 pi electrocyclizations.
• Total Synthesis of Two Naphthoquinone Antibiotics, Psychorubrin and Pentalongin, and Their C(1)-Substituted Alkyl and Aryl Derivatives
  作者：Bart Kesteleyn、Norbert De Kimpe、Luc Van Puyvelde

  DOI：10.1021/jo9811975

  日期：1999.2.1

  The synthesis of 1-alkyl- and 1-aryl-1H-naphtho[2,3-c]pyran-5,10-dione bearing a C(3)-C(4) double bond, was performed by two alternative cyclization strategies of 2,3-disubstituted 1,4-naphthoquinones. Lemieux-Johnson oxidation of 2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalenes and subsequent oxidative demethylation of the intermediate 3,4-dihydro-5,10-dimethoxy-1H-naphtho[2,3 -c]pyran-3-oles to the corresponding 3,4-dihydro-3-hydroxy-1H-naphtho[2,3-c]pyran-5, 10-diones gave, after acid-catalyzed dehydration, the de shed 1H-naphtho[2,3-c]pyran-5,10-diones. Alternatively, the pyranonaphthoquinone ring system was constructed by intramolecular acid-catalyzed condensation of(3-hydroxymethyl-1,4-naphthoquinone-2-yl)acetaldehyde acetals. Using this synthetic approach, the synthesis of two naturally occurring naphthoquinone antibiotics, pentalongin and psychorubrin, is reported.