(2R,3R,4R,54aS,12aS)-2-hydrohymethyl-3,4-dihydroxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione | 139147-83-4

• 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-hydrohymethyl-3,4-dihydroxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione
• 英文别名: (2R,3S,4S,4aR,12aS)-2-hydroxymethyl-3,4,-dihydroxy-3,4,4a,12a-tetrahydro-2H-naphtho[2,3-b]pyrano[2,3-e][1,4]-oxathiine-6,11-dione；U-286；(2R,3S,4S,4aR,12aS)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,12a-tetrahydro-2H-naphtho[2,3-b]pyrano[2,3-e][1,4]oxathiine-6,11-dione；(3S,5R,6S,7S,8R)-6,7-dihydroxy-5-(hydroxymethyl)-4,9-dioxa-2-thiatetracyclo[8.8.0.03,8.012,17]octadeca-1(10),12,14,16-tetraene-11,18-dione
• CAS: 139147-83-4
• 化学式: C₁₆H₁₄O₇S
• 分子量: 350.349
• InChiKey: VWUYXIYVXWUEKE-MXHIOEFQSA-N

物化性质

• 沸点：
  606.3±55.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,54aS,12aS)-2-hydrohymethyl-3,4-dihydroxy-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 34.0h， 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 甲醇 、 sodium methylate 作用下， 生成 (2R,3R,4R,54aS,12aS)-2-hydrohymethyl-3,4-dihydroxy-12-thia-1,5-dioxa-2H,3H,4H,4aH,12H-naphthacene-6,11-dione
  参考文献：
  名称：

  Unexpected heterocyclization of 1,4-naphthoquinone thioglucosides

  摘要：

  DOI：

  10.1007/bf00959744

文献信息

• The synthesis of thioglucosides substituted 1,4-naphthoquinones and their conversion in oxathiane fused quinone-thioglucoside conjugates
  作者：Yuri E. Sabutskii、Vladimir A. Denisenko、Roman S. Popov、Sergey G. Polonik

  DOI：10.24820/ark.5550190.p010.241

  日期：——

  we describe a methodology for the preparation of thioglucosides of substituted 1,4naphthoquinones via condensation of related chloronaphthoquinones with the sodium salt of 1-thio-β-Dglucopyranose in acetone-MeOH solution and subsequent base-catalytic conversion of these monoand dithioglucosides in the linear tetracyclic quinone-carbohydrate conjugates.

  在本文中，我们描述了一种通过相关氯代萘醌与 1-硫代-β-D-吡喃葡萄糖钠盐在丙酮-甲醇溶液中的缩合以及随后这些单和二硫代葡萄糖苷的碱催化转化来制备取代的 1,4 萘醌的硫代葡萄糖苷的方法。线性四环醌-碳水化合物共轭物。
• 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 of a Thioglucoside and Its Tetracyclic Conjugate Based on 6-Bromo-1,4-naphthoquinone Derivatives
  作者：S. G. Polonik、R. S. Popov、V. V. Makhankov、Yu. E. Sabutski

  DOI：10.1134/s1070428023040036

  日期：2023.4
• 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.