aloe-emodin ω-acetate | 65615-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: aloe-emodin ω-acetate
• 英文别名: aloe-emodin acetate；Aloe emodin w-acetate；(4,5-dihydroxy-9,10-dioxoanthracen-2-yl)methyl acetate
• CAS: 65615-58-9
• 化学式: C₁₇H₁₂O₆
• 分子量: 312.279
• InChiKey: FUECAILUKAJTBR-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  213-214°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  aloe-emodin ω-acetate 在 sodium hydroxide 作用下， 反应 24.0h， 以94%的产率得到芦荟大黄素
  参考文献：
  名称：

  Preparation of functionalized juglone acetates and juglones via 1,4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin

  摘要：

  DOI：

  10.1021/jo00079a042
• 作为产物：
  描述：

  芦荟素,葡糖基蒽酮,芦荟大黄素甙 在 三氯化铁 、 tin(ll) chloride 作用下， 以 盐酸 、 水 为溶剂， 反应 1.0h， 生成 aloe-emodin ω-acetate
  参考文献：
  名称：

  An efficient total synthesis of chrysophanol and the sennoside C aglycon

  摘要：

  A rapid synthetic approach to the naturally occurring chrysophanol and the sennoside C aglycon is reported. The method involves a three-step protocol starting with commercially available aloin-A to give the two title compounds. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.08.154

文献信息

• Studies in anthracycline synthesis: simple Diels-Alder routes to pachybasin, .omega.-hydroxypachybasin, aloe-emodin, and fallacinol
  作者：Nicholas Benfaremo、Michael P. Cava

  DOI：10.1021/jo00201a033

  日期：1985.1
• Substituent effects upon the peak potentials and reductive cleavage rate constants of hydroxy- and methoxy-substituted 9,10-anthraquinones in 50% aqueous CH3CN: do they correlate?
  作者：Ronald L. Blankespoor、Elise L. Kosters、Alan J. Post、Derek P. Van Meurs

  DOI：10.1021/jo00004a049

  日期：1991.2

  A variety of hydroxy- and methoxy-substituted 2-(acetoxymethyl)-9,10-anthraquinones (2a-7a) were reduced electrochemically and with dithionite (S2O-4(2-)) in 50% aqueous CH3CN buffers over a wide pH range. Good to excellent yields of their corresponding reductive cleavage products, the substituted 2-methyl-9,10-anthraquinones 2b-7b, were obtained from most of these anthraquinone acetates, but only at higher pH. Rate constants for the reaction of 2-(acetoxymethyl)-9,10-anthraquinone (1a) with excess dithionite ranged from 1.0 x 10(-4) S-1 at pH values less than 7 to 4.0 x 10(-4) S-1 at a pH of 10, demonstrating that loss of acetate occurs in the rate-determining step and that cleavage occurs slower via the anthrahydroquinone of 1a than the conjugate base of the anthrahydroquinone. Substituent effects upon the reductive cleavage process were determined by measuring rate constants for those acetates that react cleanly with dithionite at pH 8. These effects, which are rationalized on the basis of resonance theory and intramolecular H bonding, correlate fairly well with the peak potentials (E(p)) of the reductive cleavage products of these acetates. Thus, electron-donating substituents on an anthraquinone acetate not only make it more difficult to reduce resulting in a more negative E(p) but also enhance the rate of acetate cleavage in the corresponding anthrahydroquinone.
• Preparation of functionalized juglone acetates and juglones via 1,4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin
  作者：James L. Bloomer、Kenneth W. Stagliano、Joseph A. Gazzillo

  DOI：10.1021/jo00079a042

  日期：1993.12
• An efficient total synthesis of chrysophanol and the sennoside C aglycon
  作者：Nikolai Kuhnert、Hoshiar Y. Molod

  DOI：10.1016/j.tetlet.2005.08.154

  日期：2005.10

  A rapid synthetic approach to the naturally occurring chrysophanol and the sennoside C aglycon is reported. The method involves a three-step protocol starting with commercially available aloin-A to give the two title compounds. (c) 2005 Published by Elsevier Ltd.