2-(1-hydroxyethyl)-1,4-dimethoxy-3-prop-2-enylnaphthalene | 81418-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-hydroxyethyl)-1,4-dimethoxy-3-prop-2-enylnaphthalene
• 英文别名: 2-allyl-3-(1'-hydroxyethyl)-1,4-dimethoxynaphthalene；2-allyl-3-(1-hydroxyethyl)-1,4-dimethoxynaphthalene；1-(1,4-Dimethoxy-3-prop-2-enylnaphthalen-2-yl)ethanol
• CAS: 81418-46-4
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: WCAXPEWJHKAFCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  431.7±45.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-(1-hydroxyethyl)-1,4-dimethoxy-3-prop-2-enylnaphthalene 在 ammonium cerium(IV) nitrate 、 potassium tert-butylate 、 草酸 作用下， 以 四氢呋喃 、 水 、 乙腈 、 苯 为溶剂， 反应 38.5h， 生成 1,3-dimethyl-1H-naphtho[2,3-c]pyrane-5,10-dione
  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-(1-羟基乙基)萘-1,4-二酮 在 sodium dithionite 、 potassium carbonate 作用下， 反应 26.0h， 生成 2-(1-hydroxyethyl)-1,4-dimethoxy-3-prop-2-enylnaphthalene
  参考文献：
  名称：

  Giles, Robin G.F.; Green, Ivan R.; Hugo, Victor I., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2309 - 2313

  摘要：

  DOI：

文献信息

• Synthesis of (±)-eleutherin, (±)-isoeleutherin, and their demethoxy analogues. A novel synthetic approach
  作者：Yoshinori Naruta、Hidemitsu Uno、Kazuhiro Maruyama

  DOI：10.1039/c39810001277

  日期：——

  (±)-Eleutherin (1) and (±)-isoeleutherin (3) are prepared by intramolecular cyclization to the naphthopyrans of 2-acetyl-3-allyl-8-methoxy-1, 4-napthoquinone, which is itself obtained by the Lewis acid-mediated allylation of 2-acetyl-8-methoxy-1, 4-naphthoquinone (5) with allyltrimethylstannane (7).

  通过分子内环化成2-乙酰基-3-烯丙基-8-甲氧基-1、4-萘醌的萘并吡喃而制备（±）-伊卢色林（1）和（±）-异弹性蛋白（3），其本身是通过路易斯酸介导的2-乙酰基-8-甲氧基-1，4-萘醌（5）与烯丙基三甲基锡烷（7）的烯丙基化。
• Base-induced cyclisations of naphthalenes into naphtho[2,3-c]pyrans. Application to stereospecific syntheses of (±)-isoeleutherin and (±)-deoxyquinone a dimethyl ether
  作者：Robin G. F. Giles、Ivan R. Green、Victor I. Hugo、Peter R. K. Mitchell

  DOI：10.1039/c39830000051

  日期：——

  2-(Alk-2-enyl)-3-(1-hydroxyalkyl)-1,4-dimethoxynaphthalenes are cyclised and then oxidised to naphtho[2,3-c]pyran-5,10-quinones which are naturally occurring quinones or their derivatives.

  将2-（烷基-2-烯基）-3-（1-羟基烷基）-1,4-二甲氧基萘环化，然后氧化成萘并[2,3 - c ]吡喃-5,10-醌，它们是天然存在的醌或它们的派生词。
• 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.
• Allylation of 2-alkanoyl 1,4-quinones with allylsilanes and allylstannanes. Efficient synthesis of pyranonaphthoquinone antibiotics
  作者：Hidemitsu Uno

  DOI：10.1021/jo00353a015

  日期：1986.2
• GILES, R. G. F.;GREEN, I. R.;HUGO, V. I.;MITCHELL, P. R. K.;YORKE, S. C., J. CHEM. SOC. PERKIN TRANS., 1983, N 10, 2309-2313
  作者：GILES, R. G. F.、GREEN, I. R.、HUGO, V. I.、MITCHELL, P. R. K.、YORKE, S. C.

  DOI：——

  日期：——