2,4-二乙酰基-5-甲基-间苯二酚 | 13444-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,4-二乙酰基-5-甲基-间苯二酚
• 英文名称: 2,4-diacetyl-5-methyl-resorcinol
• 英文别名: 2,4-Diacetyl-5-methyl-resorcin；1,3-Diacetyl-2,6-dihydroxy-4-methylbenzol；2,4-Diacetylorcinol；2,4-Diacetyl-orcin；1-(3-acetyl-2,4-dihydroxy-6-methylphenyl)ethanone
• CAS: 13444-19-4
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: YUHHXAPXWVJNKC-UHFFFAOYSA-N

物化性质

• 熔点：
  94–95°C
• 沸点：
  375.7±42.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二乙酰基-5-甲基-间苯二酚 在 potassium hydrogencarbonate 作用下， 生成 2,6-二羟基-4-甲基苯甲酸
  参考文献：
  名称：

  Okazaki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 547,549; dtsch. Ref. S. 190, 192

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二乙酰氧基甲苯 在 三氯化铝 作用下， 反应 1.5h， 生成 2,4-二乙酰基-5-甲基-间苯二酚
  参考文献：
  名称：

  Na⁺-Glucose Cotransporter (SGLT) Inhibitors as Antidiabetic Agents. 4. Synthesis and Pharmacological Properties of 4‘-Dehydroxyphlorizin Derivatives Substituted on the B Ring

  摘要：

  In our studies of Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents, a series of novel 4'-dehydroxyphlorizin derivatives substituted on the B ring was prepared and their effects on urinary glucose excretion were evaluated in rats. Introduction of only a small alkyl group at the 4'-position increased the activity, and 3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-beta-D-glucopyranoside (4) showed the most potent effect. To overcome hydrolysis of compound 4 by beta-glucosidase in the digestive tract, the OH groups on the glucose moiety of compound 4 were modified. Three prodrugs (5, 42, and 55) were more potent than the parent compound 4 by oral administration, and finally 3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-(6-O-methoxycarbonyl-beta-D-glucopyranoside) (5) was selected as a new promising candidate. Compound 5 was metabolized mainly by liver esterase to the active form (4), which was about 10 times more potent than 5 in inhibiting SGLT. In oral glucose tolerance test in db/db mice, compound 5 dose-dependently suppressed the elevation of glucose levels. Single administration of 5 reduced hyperglycemia concurrently with increase of glucose excretion into urine in diabetic KK-A(y) mice. Furthermore, compound 5 suppressed the elevation of blood glucose levels but did not lower it below the normal level even in fasted conditions in KK-A(y) mice. Additionally, long-term treatment with 5 dose-dependently reduced hyperglycemia and HbA1c in KK-A(y) mice. These pharmacological data strongly suggest that compound 5 has a therapeutic potential in the treatment of NIDDM.

  DOI：

  10.1021/jm990175n

文献信息

• Biocatalytic site- and enantioselective oxidative dearomatization of phenols
  作者：Summer A. Baker Dockrey、April L. Lukowski、Marc R. Becker、Alison R. H. Narayan

  DOI：10.1038/nchem.2879

  日期：2018.2

  Biocatalytic site- and enantioselective oxidative dearomatization of phenols Biocatalytic site- and enantioselective oxidative dearomatization of phenols, Published online: 13 November 2017; doi:10.1038/nchem.2879NatureArticleSnippet(type=short-summary, markup= Within natural product biosynthetic pathways, nature has evolved highly selective catalysts capable of complexity generating reactions. Leveraging

  酚类的生物催化位点和对映选择性氧化脱芳构化 苯酚的生物催化位点和对映选择性氧化脱芳构化，在线发布：2017 年 11 月 13 日；doi：10.1038/nchem.2879NatureArticleSnippet（类型=简短摘要，标记= 在天然产物生物合成途径中，大自然已经进化出能够产生复杂反应的高选择性催化剂。利用这些工具，一套具有互补位点和立体选择性的催化剂已应用于酚类化合物的氧化脱芳构化，使酚类一锅法转化为各种天然产物。, isJats=true)
• Pyridon-, Pyrazol- und Pyrimidin-Derivate aus 3,5-Diacyl-4-pyronen
  作者：Fritz Eiden、Ernst-Günther Teupe

  DOI：10.1002/ardp.19793121013

  日期：——

  Die 3,5‐Diacyl‐4‐pyrone 7a und 7b wurden mit Ammoniumacetat, Benzylamin, Hydrazin und Hydrazin‐Derivaten sowie Benzamidin umgesetzt. Dabei entstanden Pyridon‐, Pyrazol‐, Dipyrazolyl‐keton‐, Pyrazolyl‐pyrazol‐, Pyrimidin‐, Pyrazolyl‐pyrimidin‐ und Pyrazolyl‐pyrimidinyl‐keton‐Derivate.

  Die 3,5-Diacyl-4-pyrone 7a 和 7b wurden mit Ammoniumacetat, Benzylamin, Hydrazin und Hydrazin-Derivaten sowie Benzamidin umgesetzt。Dabei entstanden Pyridon-, Pyrazol-, Dipyrazolyl-keton-, Pyrazolyl-pyrazol-, Pyrimidin-, Pyrazolyl-pyrimidin- and Pyrazolyl-pyrimidinyl-keton-Dirivate。
• Synthesis, structural elucidation and DFT studies of ortho-hydroxy acetophenones
  作者：Saikat K. Seth、Dipak K. Hazra、Monika Mukherjee、Tanusree Kar

  DOI：10.1016/j.molstruc.2009.08.013

  日期：2009.11

  ortho-hydroxy acetophenones, namely 2,6-dihydroxy-4-methyl acetophenone [C9H10O3] (1) and 2,4-dihydroxy-3-acetyl-6-methyl acetophenone [C11H12O4] (2) have been synthesized and characterized by spectroscopic and X-ray structural studies. Compound (1) crystallizes in monoclinic system, space group P21/c, with a = 3.888(3) A, b = 26.974(17) A, c = 14.940(9) A, β = 91.919(8)°, Z = 8, whereas compound (2) crystallizes

  摘要 合成并表征了两种邻羟基苯乙酮，即 2,6-二羟基-4-甲基苯乙酮 [C9H10O3] (1) 和 2,4-二羟基-3-乙酰-6-甲基苯乙酮 [C11H12O4] (2)通过光谱和 X 射线结构研究。化合物(1)在单斜晶系中结晶，空间群P21/c，a = 3.888(3) A, b = 26.974(17) A, c = 14.940(9) A, β = 91.919(8)°, Z = 8, 而化合物 (2) 在正交晶系中结晶, 空间群 Pbca, a = 7.255(2) A, b = 14.410(4) A, c = 18.332(1) A, Z = 8。 ( 1) 表现出分子间 O–H…O 氢键形成平行链沿 (0 1 0) 方向传播，而在 (2) 中，分子间 C–H…O 氢键和 π–π 相互作用的组合生成二维网络。
• Desai; Mavani, Proceedings - Indian Academy of Sciences, Section A, 1947, vol. 25, p. 353,356
  作者：Desai、Mavani

  DOI：——

  日期：——
• Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1942, vol. <2> 160, p. 33,35
  作者：Mauthner

  DOI：——

  日期：——