3-isopropyl-1,5-diacetoxybenzene | 97025-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-isopropyl-1,5-diacetoxybenzene
• 英文别名: 3,5-diacetoxy-1-isopropylbenzene；m-Isopropylresorcinyl-diacetat；(3-Acetyloxy-5-propan-2-ylphenyl) acetate；(3-acetyloxy-5-propan-2-ylphenyl) acetate
• CAS: 97025-07-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: SWSCAFFUYAIHGM-UHFFFAOYSA-N

物化性质

• 沸点：
  300.6±22.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-isopropyl-1,5-diacetoxybenzene 在 三氯化铝 作用下， 以 氯苯 为溶剂， 反应 1.0h， 以77%的产率得到2',6'-dihydroxy-4'-iso-propylacetophenone
  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
• 作为产物：
  描述：

  5-isopropylbenzene-1,3-diol 、 乙酸酐 在 吡啶 作用下， 生成 3-isopropyl-1,5-diacetoxybenzene
  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

• Aerobic oxidation of 1,3,5-triisopropylbenzene using N-hydroxyphthalimide (NHPI) as key catalyst
  作者：Yasuhiro Aoki、Naruhisa Hirai、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/j.tet.2005.08.087

  日期：2005.11

  The first systematic study on the aerobic oxidation of 1,3,5-triisopropylbenzene was examined by the use of N-hydroxyphthalimide (NHPI) as a key catalyst. It was found that 1,3,5-triisopropylbenzene was efficiently oxidized with 02 in the presence of a catalytic amount of NHPI and azobisisobutyronitrile (AIBN) at 75 degrees C. Upon treatment of the resulting products with sulfuric acid followed by acetic anhydride led to 5-acetoxy-1,3-diisopropyl benzene and 3,5-diacetoxy-1-isopropyl benzene as major products and a small amount of 1,3,5-triacetoxybenzene. When t-butyl peroxypivalate (BPP) was employed as a radical initiator, the oxidation could be achieved in good yield even at 50 degrees C. This oxidation provides a facile method for preparing phenol derivatives bearing an isopropyl moiety, which can be used as pharmaceutical starting materials. (c) 2005 Elsevier Ltd. All rights reserved.