2,3,4,7-tetrahydro-5-(2-hydroxyethyl)-2,6-dimethyl-4,7-dioxo-1H-indene-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,7-tetrahydro-5-(2-hydroxyethyl)-2,6-dimethyl-4,7-dioxo-1H-indene-2-carboxylic acid
• 英文别名: (+/-)-puraquinonic acid；puraquinonic acid；5-(2-hydroxyethyl)-2,6-dimethyl-4,7-dioxo-1,3-dihydroindene-2-carboxylic acid
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: VARWYGCUQOXJRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2,3,7,8-tetrahydro-5H-4,9-dimethoxy-2-methyl-1-oxo-6-oxacyclopenta[b]naphthalen-2-carboxylate 在 吡啶-2,6-二羧酸 n-氧化物 、 lithium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 ammonium cerium(IV) nitrate 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 19.17h， 生成 2,3,4,7-tetrahydro-5-(2-hydroxyethyl)-2,6-dimethyl-4,7-dioxo-1H-indene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of (±)-Puraquinonic Acid:  An Inducer of Cell Differentiation

  摘要：

  Puraquinonic acid (1) was synthesized from 2,5-dimethoxybenzoic acid by way of isochroman 2 and the indanone derivative 3, a Nazarov cyclization being used to construct the five-membered ring.

  DOI：

  10.1021/jo001523s

文献信息

• Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd⁰-Catalyzed Asymmetric C(sp³)–H Activation
  作者：Romain Melot、Marcus V. Craveiro、Thomas Bürgi、Olivier Baudoin

  DOI：10.1021/acs.orglett.8b04086

  日期：2019.2.1

  divergent enantioselective synthesis of (nor)illudalane sesquiterpenes was designed by using a Pd0-catalyzed asymmetric C(sp3)–H arylation as a key step to control the isolated, highly symmetric quaternary stereocenter of the target molecules. A matched combination of chiral substrate and catalyst proved optimal to reach good levels of stereoselectivity. This approach enabled the synthesis of three

  通过使用Pd 0催化的不对称C（sp 3）-H芳基化作为控制目标分子离体的，高度对称的四元立体中心的关键步骤，设计了（正）伊拉达拉烷倍半萜的不同对映体选择性合成。手性底物和催化剂的匹配组合被证明是最佳的，可以达到良好的立体选择性。该方法使得能够合成三种（去甲）illudalanes，包括首次以对映体富集形式合成的（S）-地苯醌和（S）-鲁su香酚F。
• Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp³)–H Activation Strategy
  作者：Romain Melot、Marcus V. Craveiro、Olivier Baudoin

  DOI：10.1021/acs.joc.9b01669

  日期：2019.10.18

  Three (nor)illudalane sesquiterpenes were synthesized from a common intermediate in racemic and enantioenriched forms using Pd0-catalyzed C(sp3)-H arylation as a key step. The configuration of the isolated, highly symmetric quaternary stereocenter of the target molecules was controlled through a matched combination of chiral substrate and catalyst. Moreover, the recently developed Ir-catalyzed C-H

  使用Pd0催化的C（sp3）-H芳基化为关键步骤，从外消旋和对映体富集形式的一种常见中间体合成了三（正）伊拉达拉烷倍半萜。通过手性底物和催化剂的匹配组合来控制靶分子的分离的，高度对称的四元立体中心的构型。此外，采用最近开发的Ir催化的CH硼化/ Cu催化的甲基化方法将甲基安装在苯环上。这种策略允许高效合成外消旋和（S）构型的嘌呤奎尼酸，地喹醌和russujaponol F.
• A synthesis of puraquinonic acid
  作者：Soleiman Hisaindee、Derrick L.J Clive

  DOI：10.1016/s0040-4039(01)00144-7

  日期：2001.3

  2-Methyl-1,4-benzenediol (10) was acylated with alpha -chloroisobutyroyl chloride and converted by treatment with AlCl3 into the indanone derivative 12, which was elaborated into the substituted indane acid 24. Oxidation then afforded racemic puraquinonic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of (±)-Puraquinonic Acid:  An Inducer of Cell Differentiation
  作者：Derrick L. J. Clive、Mousumi Sannigrahi、Soleiman Hisaindee

  DOI：10.1021/jo001523s

  日期：2001.2.1

  Puraquinonic acid (1) was synthesized from 2,5-dimethoxybenzoic acid by way of isochroman 2 and the indanone derivative 3, a Nazarov cyclization being used to construct the five-membered ring.