trans-2-(1-hydroxyethyl)-1,4-dimethoxy-3-(1-propenyl)naphthalene | 79054-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-2-(1-hydroxyethyl)-1,4-dimethoxy-3-(1-propenyl)naphthalene
• 英文别名: trans-2-(1-hydroxyethyl)-1,4-dimethoxy-3-prop-1-enylnaphthalene；1-[1,4-dimethoxy-3-[(E)-prop-1-enyl]naphthalen-2-yl]ethanol
• CAS: 79054-79-8
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: JAUFIOVRTSEQFQ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 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：

  trans-2-(1-hydroxyethyl)-1,4-dimethoxy-3-(1-propenyl)naphthalene 在 ammonium cerium(IV) nitrate 、 草酸 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 36.5h， 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-allyl-3-bromo-1,4-naphthoquinone 在 盐酸 、 氢氧化钾 、 正丁基锂 、 potassium tert-butylate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 8.17h， 生成 trans-2-(1-hydroxyethyl)-1,4-dimethoxy-3-(1-propenyl)naphthalene
  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

• Syntheses of naphtho[2,3-c]pyran-5,10-quinones using ceric ammonium nitrate
  作者：Trevor A. Chorn、Robin G. F. Giles、Peter R. K. Mitchell、Ivan R. Green

  DOI：10.1039/c39810000534

  日期：——

  Two 2-(alk-1-enyl)-3-(1-hydroxyalkyl)-1,4-dimethoxynaphthalenes are oxidised with silver(II) oxide to the corresponding naphthoquinones, while oxidation with cerium(IV) ammonium nitrate affords derivatives of the title compounds.

  将两个2-（烷-1-烯基）-3-（1-羟烷基）-1,4-二甲氧基萘用氧化银（II）氧化为相应的萘醌，而用硝酸铈（IV）铵氧化则可得到标题化合物。
• Synthesis of the aphin-related (±)-7,9-dideoxyquinone A and (±)-7,9-dideoxyquinone A′
  作者：Trevor A. Chorn、Robin G. F. Giles、Ivan R. Green、Peter R. K. Mitchell

  DOI：10.1039/p19830001249

  日期：——

  The oxidative cyclisation of 3-(1-hydroxyethyl)-,1,4-dimethoxy-2-prop-1-enylnaphthalene with four equivalents of ceric ammonium nitrate to afford two 4-hydroxy-1,3-dimethylnaphtho[2,3-c]pyran-5,10-quinones with the same stereochemistry as quinones A and A′, derivatives of the aphid pigments protoaphin-fb and protoaphin-sl, is described. Certain aspects of the mechanism have been established.

  3-（1-羟乙基）-，1,4-二甲氧基-2-丙-1-烯萘与四当量硝酸铈铵的氧化环化反应，得到两个4-羟基-1,3-二甲基萘[2,3-描述了具有与醌A和A'相同的立体化学的c ] pyran-5,10-醌，这是蚜虫色素protoaphin- fb和protoaphin- sl的衍生物。该机制的某些方面已经建立。
• Isochromenes and their quinones through cyclisations with bisacetonitriledichloropalladium(II)
  作者：Robin G.F. Giles、Ivan R. Green、C.Peter Taylor

  DOI：10.1016/s0040-4039(99)00899-0

  日期：1999.6

  Bisacetonitriledichloropalladium(II) is found to cyclise ortho-alkenylbenzyl alcohols rapidly to the corresponding isochromenes. The reaction also proceeds rapidly for a 2-allyl-3-hydroxyalkyl-1,4-naphthoquinon when the product is a benzoisochromenequinone. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Giles, Robin G.F.; Green, Ivan R.; Hugo, Victor I., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2309 - 2313
  作者：Giles, Robin G.F.、Green, Ivan R.、Hugo, Victor I.、Mitchell, Peter R.K.、Yorke, Selwyn C.

  DOI：——

  日期：——
• CHORN T. A.; GILES R. G. F.; MITCHELL P. R. K.; GREEN I. R., J. CHEM. SOC. CHEM. COMMUN., 1981, NO 11, 534-535
  作者：CHORN T. A.、 GILES R. G. F.、 MITCHELL P. R. K.、 GREEN I. R.

  DOI：——

  日期：——