thiaplidiaquinone A

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: thiaplidiaquinone A
• 英文别名: 6-(2,6-Dimethylhepta-1,5-dienyl)-4-(3,7-dimethylocta-2,6-dienyl)-2-hydroxy-8,8-dioxo-6,9,10,11-tetrahydrochromeno[4,3-g][1,4]benzothiazine-7,12-dione；6-(2,6-dimethylhepta-1,5-dienyl)-4-(3,7-dimethylocta-2,6-dienyl)-2-hydroxy-8,8-dioxo-6,9,10,11-tetrahydrochromeno[4,3-g][1,4]benzothiazine-7,12-dione
• 化学式: C₃₄H₄₁NO₆S
• 分子量: 591.769
• InChiKey: QDJNMAHTJHYJNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-dibromo-5-methoxy-2-(methoxymethoxy)benzene 在 四(三苯基膦)钯 、 正丁基锂 、 salcomine 、 copper(I) bromide dimethylsulfide complex 、 camphor-10-sulfonic acid 、 硝酸 、 caesium carbonate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 103.67h， 生成 thiaplidiaquinone A 、 6-(2,6-dimethylhepta-1,5-dienyl)-4-(3,7-dimethylocta-2,6-dienyl)-2-hydroxy-11,11-dioxo-6,8,9,10-tetrahydrochromeno[3,4-g][1,4]benzothiazine-7,12-dione
  参考文献：
  名称：

  Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A

  摘要：

  A concise total synthesis of the apoptosis-inducing, marine metabolite thiaplidiaquinone A is described. The key ring forming steps are both based on biosynthetic considerations and involve the construction of the central benzo[c]chromene quinone unit by an extremely facile oxa-6 pi-electrocyclic ring closure reaction of an ortho-quinone intermediate, derived by tautomerization of a bis-benzoquinone, readily accessed from two simple phenolic precursors. This is followed by the installation of the 1,4-thiazine-dioxide ring by reaction of the benzo[c]chromene quinone with hypotaurine.

  DOI：

  10.1021/jo301738u

文献信息

• Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A
  作者：Anna Carbone、Catherine L. Lucas、Christopher J. Moody

  DOI：10.1021/jo301738u

  日期：2012.10.19

  A concise total synthesis of the apoptosis-inducing, marine metabolite thiaplidiaquinone A is described. The key ring forming steps are both based on biosynthetic considerations and involve the construction of the central benzo[c]chromene quinone unit by an extremely facile oxa-6 pi-electrocyclic ring closure reaction of an ortho-quinone intermediate, derived by tautomerization of a bis-benzoquinone, readily accessed from two simple phenolic precursors. This is followed by the installation of the 1,4-thiazine-dioxide ring by reaction of the benzo[c]chromene quinone with hypotaurine.