(2R,3R,4R,54aS,12aS)-2-acetoxymethyl-3,4-diacetoxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione | 139147-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3R,4R,54aS,12aS)-2-acetoxymethyl-3,4-diacetoxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione
• 英文别名: (2R,3R,4S,4aR,12aS)-2-[(acetyloxy)methyl]-6,11-dioxo-3,4,4a,6,11,12a-hexahydro-2H-naphtho[2,3-b]pyrano[2,3-e][1,4]oxathiine-3,4-diyl diacetate；[(3S,5R,6R,7S,8R)-6,7-diacetyloxy-11,18-dioxo-4,9-dioxa-2-thiatetracyclo[8.8.0.03,8.012,17]octadeca-1(10),12,14,16-tetraen-5-yl]methyl acetate
• CAS: 139147-84-5
• 化学式: C₂₂H₂₀O₁₀S
• 分子量: 476.461
• InChiKey: NJUKYOCSAOODHG-NUMOICBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,54aS,12aS)-2-acetoxymethyl-3,4-diacetoxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione 在 吡啶 、 sodium dithionite 、 水 、 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Synthesis and properties of fused tetracyclic derivatives of 1,4-naphthoquinone thioglycosides

  摘要：

  通过1-硫代-d-木糖、1-硫代-L-阿拉伯糖、1-硫代-d-半乳糖、1-硫代-d-半乳糖、1-硫代-d-半乳糖的全O-乙酰化衍生物缩合合成了一系列1,4-萘醌O-乙酰硫代糖苷。硫代-d-甘露糖和1-硫代麦芽糖与3-氯-2-甲氧基-1,4-萘醌。它们用 MeONa/MeOH 进行脱乙酰化，同时进行杂环化，生成含直链碳水化合物的四环醌。碳水化合物和醌环转接的四环化合物难溶于水和有机溶剂。

  DOI：

  10.1007/s11172-009-0135-y
• 作为产物：
  描述：

  2,3-bis(tetra-O-acetyl-β-D-glucopyranosylthio)-1,4-naphthoquinone 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (2R,3R,4R,54aS,12aS)-2-acetoxymethyl-3,4-diacetoxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione
  参考文献：
  名称：

  Reaction of acetylated 1,4-naphthoquinone thioglucosides with nucleophilic reagents

  摘要：

  Acetylated thioglucosides of the 1,4-naphthoquinone series readily undergo heterocyclization into linear tetracyclic 2,3-(2'-oxy-beta-D-glucopyranosyl-1'-thio)-1,4-naphthoquinone under the action of MeONa/MeOH. The treatment of these thioglucosides with NH3/MeOH affords 2-amino-3-(glucopyranosyl-1'-thio)-1,4-naphthoquinone.

  DOI：

  10.1007/bf01433995

文献信息

• Unexpected heterocyclization of 1,4-naphthoquinone thioglucosides
  作者：A. M. Tolkach、S. G. Polonik、N. I. Uvarova

  DOI：10.1007/bf00959744

  日期：1991.12
• Synthesis and properties of fused tetracyclic derivatives of 1,4-naphthoquinone thioglycosides
  作者：S. G. Polonik、V. A. Denisenko

  DOI：10.1007/s11172-009-0135-y

  日期：2009.5

  A series of 1,4-naphthoquinone O-acetylthioglycosides have been synthesized by the condensation of fully O-acetylated derivatives of 1-thio-d-xylose, 1-thio-L-arabinose, 1-thio-d-galactose, 1-thio-d-mannose, and 1-thiomaltose with 3-chloro-2-methoxy-1,4-naphtho-quinone. Their deacetylation with MeONa/MeOH proceeded with simultaneous heterocyclization to yield linear carbohydrate-containing tetracyclic quinones. Tetracycles with trans junction of the carbohydrate and quinone rings are poorly soluble in water and organic solvents.

  通过1-硫代-d-木糖、1-硫代-L-阿拉伯糖、1-硫代-d-半乳糖、1-硫代-d-半乳糖、1-硫代-d-半乳糖的全O-乙酰化衍生物缩合合成了一系列1,4-萘醌O-乙酰硫代糖苷。硫代-d-甘露糖和1-硫代麦芽糖与3-氯-2-甲氧基-1,4-萘醌。它们用 MeONa/MeOH 进行脱乙酰化，同时进行杂环化，生成含直链碳水化合物的四环醌。碳水化合物和醌环转接的四环化合物难溶于水和有机溶剂。
• Reaction of acetylated 1,4-naphthoquinone thioglucosides with nucleophilic reagents
  作者：S. G. Polonik、A. M. Tolkach、N. I. Uvarova

  DOI：10.1007/bf01433995

  日期：1996.2

  Acetylated thioglucosides of the 1,4-naphthoquinone series readily undergo heterocyclization into linear tetracyclic 2,3-(2'-oxy-beta-D-glucopyranosyl-1'-thio)-1,4-naphthoquinone under the action of MeONa/MeOH. The treatment of these thioglucosides with NH3/MeOH affords 2-amino-3-(glucopyranosyl-1'-thio)-1,4-naphthoquinone.