trans 3-(1'-hydroxyethyl)-1,4,5-trimethoxy-2-(prop-1'-enyl)naphthalene | 175233-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans 3-(1'-hydroxyethyl)-1,4,5-trimethoxy-2-(prop-1'-enyl)naphthalene
• 英文别名: 3-(1-hydroxyethyl)-1,4,5-trimethoxy-2-prop-1-enylnaphthalene；1-[1,4,8-trimethoxy-3-[(E)-prop-1-enyl]naphthalen-2-yl]ethanol
• CAS: 175233-22-4
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: YASAYHFSFXMHRJ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans 3-(1'-hydroxyethyl)-1,4,5-trimethoxy-2-(prop-1'-enyl)naphthalene 在 silver(II) oxide 、 ammonium cerium(IV) nitrate 、 pyridinium dichromate on alumina 、 硝酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.83h， 生成 Hongconin
  参考文献：
  名称：

  A High Yielding Synthesis of Racemic Hongconin

  摘要：

  Racemic hongconin 1 has been synthesized from adduct 2 formed by reaction between 1-methoxycyclohexa-1,4-diene and benzoquinone. The synthetic strategy includes Fries and Claisen rearrangements, base and cerium(IV) initiated pyran ring formation, C-4 pyran ring hydroxylation and silver(II) mediated oxidation.

  DOI：

  10.1080/00397919608003690
• 作为产物：
  描述：

  3-(1'-羟基乙基)-1,4,5-三甲氧基-2-(丙-2'-烯基)萘 在 双(乙腈)氯化钯(II) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到trans 3-(1'-hydroxyethyl)-1,4,5-trimethoxy-2-(prop-1'-enyl)naphthalene
  参考文献：
  名称：

  A High Yielding Synthesis of Racemic Hongconin

  摘要：

  Racemic hongconin 1 has been synthesized from adduct 2 formed by reaction between 1-methoxycyclohexa-1,4-diene and benzoquinone. The synthetic strategy includes Fries and Claisen rearrangements, base and cerium(IV) initiated pyran ring formation, C-4 pyran ring hydroxylation and silver(II) mediated oxidation.

  DOI：

  10.1080/00397919608003690

文献信息

• 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。
• Giles, Robin G. F.; Green, Ivan R.; Hugo, Victor I., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2383 - 2388
  作者：Giles, Robin G. F.、Green, Ivan R.、Hugo, Victor I.、Mitchell, Peter R.K.、Yorke, Selwyn C.

  DOI：——

  日期：——
• A High Yielding Synthesis of Racemic Hongconin
  作者：Ivan R. Green、Victor I. Hugo、F. Oosthuizen、Robin G. F. Giles

  DOI：10.1080/00397919608003690

  日期：1996.3

  Racemic hongconin 1 has been synthesized from adduct 2 formed by reaction between 1-methoxycyclohexa-1,4-diene and benzoquinone. The synthetic strategy includes Fries and Claisen rearrangements, base and cerium(IV) initiated pyran ring formation, C-4 pyran ring hydroxylation and silver(II) mediated oxidation.